Gerrymandering is dominating the national political conversation.

Virginia voters last week narrowly approved a constitutional amendment allowing the state to redraw its political maps ahead of the 2026 midterms—joining a brushfire of mid-decade gerrymandering sparked in Texas.

But mapmaking isn’t just a game for congressional districts. Chicago local government uses cartoonish cartography, too. And unlike the craze of partisan gerrymandering sweeping states across the nation, there is no “tit-for-tat” excuse for Chicago’s system.

It is simply voter suppression. And there’s a straightforward fix to stop it.

Chicago’s gerrymandered ward maps

The waterslide. The pool noodle. The barbell. The seesaw. These are a few of the terms used to describe the boundaries of Chicago’s 36th Ward.

An equally apt descriptor: the punishment.

Incumbent 36th Ward Ald. Gil Villegas led Latino Caucus opposition to the ward maps following the 2020 census. Consequently, his home ended up 8 miles away from some of his new constituents.

At least his home was still in the ward. The most gerrymandered ward in Chicago following the 2010 Census was the 2nd Ward. Dubbed the “lobster,” its bizarre shape was owed in part to drawing the incumbent’s residence out of the ward entirely.

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The petty political dramas that play out in mapmaking create problems for neighborhoods like Englewood, which is sliced up across five wards. One longtime resident summed up the political dynamic: “too many cooks in the kitchen.”

All of this happens because under Chicago’s current mapmaking system, politicians pick their voters.

How Chicago politicians pick their voters

State law requires Chicago to redraw its ward boundaries after each federal census. Those wards must have roughly equal numbers of residents.

If City Council can’t agree on a map by the deadline, any group of 10 aldermen can put a map to voters via referendum. This has only happened once in the city’s modern history. In 1992, Chicago voters approved a map drawn by the Daley administration and aldermanic allies. (For context: The political fight following the 1990 census was so contentious that Ald. Dorothy Tillman allegedly pulled a gun at a community meeting on the topic.)

In practice, this system means City Council whips 41 votes every decade to pass a new map. Members trade favors behind closed doors in a “map room” at City Hall, drawing boundaries block-by-block, often in concert with the sitting mayor.

How other big cities draw council maps

The sordid details of big-city political mapmaking are typically hidden from the public.

But in Los Angeles, those details leaked. In 2022, a secret recording surfaced that contained a conversation between three City Council members about gerrymandering, laced with racist insults, recorded at a local union headquarters.

In the wake of that scandal, council members passed an amendment to the LA city charter creating an independent mapmaking commission for the 15 city council districts. Voters approved that charter amendment overwhelmingly.

In New York City, the process for local mapmaking is still vulnerable to political meddling. But the city charter does prevent monstrosities like Chicago’s 36th Ward, mandating that a district “shall be no more than twice as long as it is wide.”

Chicago has no city charter to govern basic governance matters, like how to draw its City Council maps. Getting one requires a change to state law.

Short of that, voters should demand candidates for office in the February 2027 municipal elections support creating an independent citizens commission to redraw the maps following the 2030 census.1

In the news

Last week I joined ABC7, Fox32, and WGN Radio to discuss the “millionaires tax” constitutional amendment highlighted in last week’s edition of The Last Ward.

The constitutional amendment failed to secure enough Democratic votes to pass the full House last week. It will not appear on the November ballot.

How should Chicago deal with the city’s persistent financial problems?

That might be the most common question posed to Mayor Brandon Johnson since he took office in 2023.

And his answer has always been a variation on one theme: Hike taxes on millionaires.

So I joined WTTW’s Chicago Tonight to debate whether Johnson is right. You can watch the full debate here.

Discussion around a millionaires tax in Illinois is heating up due to two constitutional amendments introduced in Springfield: HJRCA 21 and HJRCA 26.

If either passes with supermajorities in the House and Senate, and voters approve at the ballot box, the state would impose an extra 3% tax on income over $1 million.1

To be clear: these proposals are unlikely to end up on the ballot in November.2

But the perennial demand to scrap the Illinois Constitution’s flat income tax requirement is still worth taking seriously. Even the mere discussion of taxes like these can chase away opportunity and investment.3

Here are three reasons Illinois lawmakers should reject Johnson’s demand.

1. It would make Illinois’ biggest problem even worse

Illinois lost nearly 1 million taxpayers on net to migration over the last decade. And those earners took a combined $88 billion in income with them, according to IRS data. It was the second-worst loss of taxpayers in the nation over that time period.

For context, that’s as if the seven largest cities in Illinois outside of Chicago were wiped off the map: Aurora, Joliet, Naperville, Rockford, Elgin, Springfield, and Peoria.

The taxpayers Illinois is losing the fastest? Those earning over $200,000: the highest income bracket published in IRS migration data.

Chicago lawmakers and Gov. JB Pritzker torpedoed Johnson’s “head tax” proposal last year because they understood it would throw up a red flag to those seeking to invest here.

The same argument applies to the millionaires tax. Illinois and Chicago can’t afford to accelerate the loss of higher-income earners. And must do everything in their power to reverse the trend.

Think of it this way: If Illinois simply broke even on migration over the last decade, Chicago and Illinois wouldn’t be staring down budget deficits today.

2. It unfairly punishes small businesses

Small businesses create the overwhelming majority of new jobs in Illinois. In Cook County, businesses with fewer than 20 employees have driven all new jobs growth since the COVID-19 pandemic.

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But a “millionaires tax” would hit roughly 22,000 of those Illinois small businesses (S Corps) that take in more than $1 million, hurting hiring and investment across the state.

Meanwhile, large corporations (C Corps) in Illinois would not pay the new millionaire’s surcharge.

3. Massachusetts already learned this lesson the hard way

Massachusetts passed a new 4% tax on income over $1 million in 2023. New IRS data show in the first full year after that, Massachusetts saw:

• $4.2 billion in Adjusted Gross Income (AGI) leave the commonwealth, up 8% from $3.9 billion the previous year.

• 70% of that loss came from high-income earners, which is double the share from just a few years earlier.

Most concerningly, total AGI in Massachusetts shrunk year-over-year, meaning higher taxes are hitting a smaller tax base.

Massachusetts did get a sugar high of new tax revenue. But it came at the cost of shrinking the pie for everyone.

Illinois should not be copying this model.

In the news

May Day update: Mayor Brandon Johnson and the Chicago Teachers Union have failed to secure the school board votes necessary to make May 1 a non-attendance day. Thanks to all The Last Ward readers who contacted their school board member following last week’s newsletter!4

New zoning chair: The Chicago City Council elected Ald. Gil Villegas as chair of the powerful Zoning Committee. His selection, compared with who Johnson wanted as chair (socialist Ald. Byron Sigcho-Lopez), is among the biggest swings in favor of healthier economic growth in Chicago this decade.

Villegas was a featured speaker at the Chicago Policy Center’s Charter Symposium at Northwestern’s Pritzker School of Law, and has been a champion of governance reform to make City Council a true legislative branch.

ShotSpotter update: The Last Ward was first to report on the connection between former Deputy Mayor of Community Safety Garien Gatewood’s firing and the severely delayed procurement process for a new gunshot detection technology to replace ShotSpotter. Now, City Council is demanding answers. Last week, 35 aldermen signed on to a new resolution demanding hearings “on status and reason for delays of Chicago Police Department’s procurement of [a] new records management system and appropriation for procuring [a] new acoustic gunshot technology system.”

Crisis Cast: I joined Thom Serafin and Lissa Druss on their podcast to talk about Illinois’ fiscal challenges and Chicago governance. (Apple Podcasts, Spotify)

Will the Chicago Teachers Union lock students out of school on May 1?

More than 300,000 Chicago schoolchildren—and their parents—still don’t know the answer to that question.

Whether schools will proceed with arts programming, senior milestones, AP exam prep, field trips and more on May Day remains up in the air.

But one thing is certain.

If the CTU and Mayor Brandon Johnson have their way, Chicago will be the only big city in the country to proactively close its public schools on May 1, according to Chicago Policy Center analysis.

Chicago is an outlier. But why?

What’s happening?

Several key actions led the district up to this point. Here’s a timeline of what you need to know.

The resolution: CTU’s House of Delegates passed a resolution in March declaring May 1 a day of “no school, no work, no shopping.”

The grievance: CTU then filed a grievance April 6, alleging Chicago Public Schools violated their contract by refusing to move a planned, teacher-led professional development day from June 5 to May 1.

The response: CPS CEO Dr. Macquline King responded to the grievance with a detailed memo to the school board, showing that while CTU’s contract does have a provision allowing for a teacher-led professional development day:

• The provision doesn’t take effect until next school year.

• The date of that professional development must be agreed upon by the union and the board.

• A professional development day is not the same as declaring a district-wide non-attendance day.

A closed-door vote: Chicago Board of Education President Sean Harden sent a brief letter to King on April 9 saying the school board had approved (in closed session) a “day of civic action” on May 1.

King reaffirms position: In response to the confusion caused by Harden, King then sent a letter to CPS staff and families stating that her position is to maintain May 1 as an instructional day. But if the school board wants to change the calendar to make it a non-attendance day, “they may convene a special Board meeting for a formal vote on this matter.”

What’s next? The school board’s next scheduled meeting is April 23, just a week before May Day. But the board could hold a special meeting before then to take a vote, with 48 hours notice to the public.1

Why is this up for debate?

Chicago’s outlier status among other big cities on May Day raises an important question.

Why is shutting down schools for a union-led protest part of a contract discussion in the first place?

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In part, it’s because of a state law passed in 2021 that repealed limits on CTU’s collective bargaining powers. There are now virtually no limits on what CTU can demand at the bargaining table, which means unlimited political moves and unlimited grievances.

It’s one of five ways state law gives CTU leadership more power than Chicago parents, students and even elected officials in deciding how schools are run.

What can you do?

Chicagoans who don’t agree with the push to close schools on May 1 should consider the following.

1. Contact your school board member: Tell your school board member to keep schools open on May 1. You can look up and contact your board member here.

2. Reject CTU-backed school board candidates in the November elections: While CTU-backed candidates lost a majority of their school board races in 2024, the board is still mostly composed of Johnson appointees backed by the union. But this November, all 20 seats and the president will be up for election.

3. Tell your state lawmaker to reinstate limits on CTU’s power: Political protest days should not be the subject of collective bargaining. State law should explicitly ban this practice. (CTU’s current contract ensures this same chaos will come up again next year around May Day. And the year after that.) Find your Illinois House and Senate member here.

4. Watch your public officials: Lawmakers’ response in this moment, or lack thereof, is worth noting. Are they denouncing the push to shut down schools? And if so, are they highlighting the state’s role in enabling it?

In the news

I joined WTTW’s Chicago Tonight to debate whether Illinois should adopt a proposed “millionaire’s tax.” More on that topic in a future edition of The Last Ward.

I also joined the Mincing Rascals on WGN to discuss how to bring professional excellence to the Chicago Police Department, the Iran war ceasefire, the May 1 walkout, and more. (Apple, Spotify, Youtube)

Chicago Bears Head Coach Ben Johnson went viral last year for his call to greatness.

“Good, better, best. Never let it rest. ‘Til your good gets better. And your better gets best.”

Chicago government has fallen short of that expectation for decades. And the Chicago Police Department is no exception.

Two landmark reports published last week provide a game plan to make the Chicago Police Department the most effective, professional, trustworthy big city police department in the country.1

Here are the five most important takeaways.

1. CPD is a national outlier on civilian staffing. And that’s costing the city real police work.

Of the 30 largest police departments in the United States, CPD has the lowest percentage of civilian employees, at less than 8% of its workforce.

For comparison, NYPD is at 31%. LAPD is at 24%.

The workforce allocation study identified 604 sworn police officers — people with badges, guns, and the authority to make arrests — currently assigned to jobs that require none of those things, such as timekeeper (42 officers), watch secretary (98 officers) and police district administrative support staff (85 officers).

These police officers are not on patrol. They’re not building relationships. They’re not responding to calls.

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CPD can move these officers into roles where sworn expertise is actually needed, and hire civilian professionals to back-fill the positions at a fraction of the cost.

This misuse of talent is hurting public safety.

2. Some neighborhoods are not proactively policed.

The workforce allocation study also measured “proactive time” — the share of a patrol officer’s shift not consumed by responding to 911 calls, handling backup, and writing reports.

The industry benchmark for proactive time is 40%. Below that level, officers are chasing the radio. Above that level, officers have enough time to build community relationships and engage in problem-solving.

CPD averages 40% proactive time citywide. But that average conceals some shockingly low numbers at the district level.

The 12th District, which includes the West Loop neighborhood, ran at just 9% proactive time. The lowest rate in the city.

As the report states bluntly: “When proactive time levels are as low as 9% ... virtually no time is available for proactive work or community engagement, and low-priority calls will frequently go without a response for extended periods of time.”

Fixing this imbalance without reducing current force in any district, according to the study, requires 273 additional patrol officers. And those slots can be filled by taking sworn officers off the jobs civilians could do instead.2

3. CPD is missing basic management fundamentals

The average Portillo’s employee often enjoys better management practices at his workplace than do rank-and-file CPD officers.

The workforce study revealed CPD lacks basic management information about its own operations. For example, the department does not have a unified system for tracking how many officers are redirected to special events, how often, or for how long. In practice, that means no reliable, centralized record of what those officers are doing.

Beyond missing data, the reports identify management practices that any professional organization would treat as standard, and that CPD has never consistently applied. Practices like:

• Standardized supervisor-to-officer ratios. Critical for performance evaluations and early intervention when officers show signs of misconduct or underperformance.

• Unity of command. Officers working with the same supervisor every day. Mentorship and accountability require stable supervisory relationships.

• Geographic integrity. Officers and supervisors working the same neighborhoods consistently is a precondition for community relationships.

• Built-in time for community engagement by every officer. This is critical for proactive problem-solving.

None of these are advanced reforms. They are the basic management systems that shape how officers show up in everyday interactions with the public.

4. Poor management is producing poor customer service.

The management failures above have a direct human consequence.

When officers have no beat integrity, they don’t know the communities they serve. When they’re chasing the radio all day, they have no time for meaningful interaction. And when there’s no standard for how to treat people, there’s no accountability when it goes wrong.

Released in tandem with the workforce allocation study was an analysis on community policing practices within CPD. Its core finding was that community policing has failed not because the concept is wrong, but because it was never actually adopted as a philosophy.3 It was adopted as a program. Far too many programs, in fact.

There are currently about 400 specialized community policing roles across nearly 40 distinct titles, running alongside 19 different departmental policies that are, in some cases, contradictory. There are at least 112 separate trainings at CPD that reference community policing concepts. And yet, one officer in a focus group put it this way: “We’ve never been trained. Yet CPD has so many trainings! Our duties are not clearly outlined.”

The practical result is that every officer in the department knows community policing is someone else’s job.

Most surprisingly, the report found CPD has no clear, department-wide framework guiding how officers are expected to engage with the public in everyday interactions.

The result, documented in community focus groups across 21 neighborhoods, is that officers are too often described as unapproachable, unwilling to engage, aggressive, or disrespectful.

The only way to fix this is to stop treating community policing as a specialized function and make it the baseline expectation for every officer in every interaction.

“If we want to build true and lasting partnership in every community, community-focused policing has to guide every member of our department, regardless of their assignment,” Superintendent Larry Snelling said last year.

“We’re committed to making the needed changes to put this into practice, and we must break down existing silos internally to ensure every officer holds the responsibility of building trust with the residents we serve.”

The department has a long way to go.

5. Governance is still a missing ingredient

Read together, these reports chart a path that does not require a fiscal miracle or a generational culture shift to begin.

Stop deploying sworn officers in administrative roles. Rebalance patrol staffing to match workload. Merge redundant community policing programs into a coherent structure. Give every officer clear expectations for community engagement as part of their daily job.

The analysis is done.

But the deepest obstacle is outside the purview of these reports: Chicago’s police governance is structured to be overly political, rather than professional.

Last week The Last Ward reported on the firing of Garien Gatewood, Brandon Johnson’s first deputy mayor of community safety. That story, and many others, show what it looks like when policing is governed by political coalition rather than professional standards.

Chicago currently has eight overlapping bodies with some claim to police accountability. Los Angeles — a city 50% larger than Chicago — manages its police department through one primary civilian body: the LA Police Commission.

As Ed Bachrach and I argued in The New Chicago Way, and as we wrote in the Chicago Sun-Times, that model — combined with a consent decree and serious charter reform — helped bring LAPD from among the most troubled big-city departments in America to one of its most improved.

CPD has the analyses and recommendations it needs. What it lacks is a governance structure that Chicagoans can trust will implement them.

That’s the piece neither report can write for us.

In the news

I joined the Ray Stevens Show on WLS to discuss recent departures from Mayor Brandon Johnson’s office.

My colleagues Micky Horstman and Mailee Smith published an analysis of the Chicago Teachers Union’s track record in the Illinois primary elections for the Chicago Tribune. More on that here.

When Garien Gatewood walked into a meeting with top mayoral aides on March 19, he thought he was there to finalize the paperwork putting one of his team members on a performance improvement plan.

He was actually walking into his own termination.

Gatewood served as Johnson’s first deputy mayor of community safety. But Chief of Staff Cristina Pacione-Zayas and Senior Adviser Jason Lee told him the administration was moving in a different direction. Gatewood was fired. Mayor Brandon Johnson never spoke to him directly. Gatewood’s deputy Manny Whitfield was fired the same day.

As Gatewood later put it, “This didn’t have anything to do with work. Just yesterday, they were tagging me on social media highlighting our work together.”

This personnel drama highlights what it looks like when a city’s public safety function is political rather than professional.

Readers of The New Chicago Way and The Last Ward know that’s not unique to Johnson’s administration. Rather, it’s baked into how Chicago government is structured.

‘Hostility toward law enforcement’

After speaking with sources close to the mayor’s office last week, it’s clear there are two main reasons Gatewood and Whitfield were fired. Both point to a public safety operation accountable to a political coalition rather than to outcomes.

First: Alyx Goodwin.

No outlet has named Goodwin as the employee at the center of the performance improvement plan (PIP) dispute. But we can confirm she was the employee in question.

Goodwin serves as a senior policy advisor in the Office of Community Safety. Before joining City Hall, she helped lead the Stop ShotSpotter campaign, the activist effort that preceded Johnson’s cancellation of the ShotSpotter contract.

Goodwin’s allies on the fifth floor include Kennedy Bartley, the mayor’s chief external affairs officer, who previously served as executive director of United Working Families, the Chicago Teachers Union-aligned organization instrumental in electing Johnson.

Bartley survived calls for her own firing in 2024 after podcast clips surfaced of her referring to police as “f---ing pigs,” and calling for the abolition of policing and prisons. The latter was captured on a recording with Goodwin.

Bartley and Goodwin stayed. Gatewood and Whitfield are gone.

When asked if there is a hostility toward law enforcement in the mayor’s office, Whitfield did not mince words.

“There is a hostility toward law enforcement among senior leadership in the mayor’s office,” he said.

Second: the gunshot detection contract.

In October 2025, Gatewood filed a formal complaint with Inspector General Deborah Witzburg accusing Pacione-Zayas and Lee—the two people who fired him—of improper interference in City Hall’s “contracting process.” The Chicago Sun-Times reported this but was careful not to specify which contracts.

One is almost certainly for a new gunshot detection system, replacing ShotSpotter.

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Office of Public Safety Administration Executive Director Era Patterson told aldermen during November 2025 budget hearings that the scoring and recommendations for the replacement bids had already been submitted to the Chief Procurement Officer.

It’s now the end of March 2026. But there’s no contract. No announcement. And no explanation.

Why the delay?

If SoundThinking (the company behind ShotSpotter) scored highest in a professional evaluation—the one the mayor’s own process produced—awarding them the contract means admitting the city went 18 months without gunshot detection for a campaign promise that accomplished little to nothing.

That would be a significant political problem for an administration heading into election season.

One more detail: Lee, who delivered Gatewood’s termination, was previously recommended for firing by the same Inspector General — for threatening to withhold public safety services from an alderman who wouldn’t vote the mayor’s way. Johnson declined to act.

As Gatewood said, “There is a culture in this office where when you work to hold people accountable, you become a target.”

How to make Chicago policing more professional, less political

Chicago’s police governance is not working well.

“I came into this role, God’s honest truth, expecting to find a dirty police department that needed to be cleaned up,” said Community Commission for Public Safety and Accountability President Anthony Driver last year.

“What I found was a dirty city — and every aspect of the city of Chicago touches the Chicago Police Department.”

The drama surrounding the mayor’s office is just one part of a fragmented, confusing, and ineffective system. At least eight overlapping bodies can claim some kind of “police accountability” function in Chicago.1

Los Angeles, by contrast, has one primary body for police oversight. The LA Police Commission.2 Plus the City Council’s Public Safety Committee.

As The New Chicago Way co-author Ed Bachrach and I wrote in the Chicago Sun-Times, this model—in concert with a consent decree and changes to the city charter—helped bring LAPD from among the most infamous big-city police departments in America to among the best.3

With every killing, Chicago officials react somberly and predictably. But with the stark contrast in organization and results between Chicago and Los Angeles, any reasonable citizen would be justified in asking if our leaders are serious about professional policing, or if they prefer to keep it political.

For the current administration, the answer seems clear. They prefer to keep it political.

In the news

CTU fails to kill the audits lawsuit

A judge last week rejected CTU’s motion for summary judgment, meaning the case now moves to discovery. The CTU produced several years of audits but has failed to assure members they will abide by their own bylaws and release audits in the future. Here’s everything you need to know.

Chicago’s Chief Homelessness Officer is out

Sources say another senior leader in Johnson’s administration will be leaving shortly.

Mincing Rascals

I joined the Mincing Rascals on WGN to discuss the tragic murder of Loyola University student Sheridan Gorman, among other topics (YouTube, Apple, Spotify).

My “green light” recommendation: Duane Powell’s series at The Land School, “1976: A Retrospective.” Last week’s edition on the work of Chicago-born producer Charles Stepney was extraordinary. You can find the schedule here.

The Washington Post published an ominous and accurate editorial last Sunday: “Chicago careens toward insolvency.”

The piece echoes a clear message from ratings agencies: Without immediate action, Chicago will become the only “junk” rated big city in the nation by the end of this budget cycle.

It’s an emergency. But Chicago’s elected officials and most of its civic institutions are not acting like it.

The typical response to this emergency has been simple: yell at Mayor Brandon Johnson to act more responsibly. Or worse, complain behind closed doors and quietly hope he changes course.

It’s not working. The mayor has ignored calls for more responsible budgeting for three years. He’s rapidly accelerated the city’s financial decline through reckless borrowing and a refusal to slow spending. Barring divine intervention, Johnson will not change.

Superman will not emerge from the fifth floor of City Hall to stop this runaway train.

(And hoping voters elect Superman as the new mayor in February 2027 isn’t enough. Far too much damage is possible between now and then.)

So what can be done?

How City Council can stop the bleeding

Chicago City Council has shown willingness to publicly embarrass Mayor Johnson. This is a new dynamic for a city in which the mayor wields king-like authority.

But there’s a difference between insurgency and statecraft. Council needs to engage in the latter.

City Council has the power to make several immediate improvements that would be credit-positive and bring lasting benefits to city government. The Civic Federation points to a few simple, short-term fixes:

• Pass an ordinance to guarantee that City Council has equal access to all financial information and expertise available to the mayor’s office.

• Elect a council president to serve as the lead budget negotiator with the mayor’s office and nominate committee chairs.

• Expand and professionalize the City Council Office of Financial Analysis.

• Expand substantive committee staff and limit their work to legislative matters rather than constituent services.

• Pass an ordinance requiring the proposed budget to be released earlier in the year, including a formal process for proposing budget amendments from the council that require response from the mayor’s office.

Johnson will not support any of this, which is exactly why the council must take matters into its own hands.

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And council members shouldn’t stop there.

Building better institutions

When Chicago was hit with two credit downgrades in February, local officials hardly made a peep.

Now watch how New York City’s independently elected comptroller, Mark Levine, reacted to a change in his city’s credit outlook last week (this is an action short of a downgrade that signals a future downgrade is more likely.)

Notice the difference?

The New York City Comptroller has the power to audit every agency, review every contract for fiscal compliance, and manage the five city pension funds as a fiduciary.

Meanwhile, Chicago’s elected treasurer is designed to be a bookkeeper with a press team.

Current Chicago Treasurer Melissa Conyears-Ervin lost her bid for Congress last Tuesday, leading insiders to suspect she’s vulnerable to a challenge in 2027. Council should transform that office into a real watchdog, with changes taking effect following next year’s election.

In fact, that was one of four structural changes recommended by the Washington Post in their recent editorial on Chicago.

All four will be familiar to readers of The Last Ward:

1. Create independent oversight of the budget.

2. Allow Chicago to access debt relief in Chapter 9 bankruptcy court.

3. Implement $1 billion in structural efficiencies identified by EY but ignored by the mayor’s office.

4. Change municipal election timing to double turnout in local elections.

Chicago doesn’t need a superhero.

It needs a better system, producing better results, that lasts beyond any one mayor.

In the news

The Wall Street Journal editorial board provided an Illinois primary election recap with their piece, “A Glimmer of Hope in Illinois.”1

An excerpt:

Voters in more than 30 counties or townships—out of 102 counties in [Illinois]—weighed in on a nonbinding ballot question asking if the state should opt into the new federal tax-credit scholarship program. Some 64% of voters said yes, and the referendum passed in all jurisdictions that have final results, says the Illinois Policy Institute (IPI) …

State lawmakers last month introduced a bill to ban the state from opting in, but Democratic state Sen. Adriane Johnson has introduced a bill to opt in. Democratic comptroller Susana Mendoza called the decision to do so an “easy one.”

Why let Illinois money go to students in other states? The answer is that too many state Democrats bend to the teachers union. The CTU gave $72,500 to the campaign of Democrat state Sen. Graciela Guzman about the time she introduced the ban on opting into the tax-credit program, says IPI.

But Tuesday’s results also showed how the union is out of step with the public. The CTU endorsed 13 candidates with primary opponents and donated hundreds of thousands of dollars to the campaigns. Five of those state candidates, plus a U.S. House contender and a Cook County commissioner, lost.

Here in Chicago, I joined WGN’s John Williams and Fox to go deeper on the Washington Post editorial.

“A Lithuanian won’t vote for a Pole, a Pole won’t vote for a Lithuanian, [and] a German won’t vote for either of them,” a Chicago politician once told University of Illinois Chicago Prof. Milton Rakove.

“But all three will vote for a ‘Turkey,’ an Irishman.”

The first two major ethnic groups who came to Chicago from Europe were the Germans and the Irish. Their differences would define the city’s political landscape for a century.

First, the Irish spoke and understood English. Many Germans did not.

Second, the Irish were neutral bystanders in centuries-old feuds between central and eastern European groups. The Germans were not.

And third—as every Chicagoan can see firsthand this weekend—the Irish were drinkers. So were the Germans. But unlike the Irish, they didn’t own the saloons around which so much of the city’s social life was organized.

This all played out at the polls.

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Of the 28 most influential Chicago aldermen of the 1890s, 24 were Irish.1 In 1926, 33 of the 50 ward committeemen for the Democratic Party were Irish.

And by 1970, despite constituting less than 10% of the city’s population, the Irish held the following leadership positions in local government:

• Mayor of Chicago (held since 1933, ~40,000 patronage jobs)

• President of Cook County (~6,000 patronage jobs)

• Cook County clerk

• Cook County assessor

• Member of the Cook County board of appeals

• Cook County state’s attorney

• Clerk of the Cook County circuit court (~1,500 patronage jobs)

• President of the park district

• Corporation counsel for the city of Chicago

• Superintendent of police

• Fire commissioner

• Superintendent of the public schools

• President of the board of education

• President of the Metropolitan Sanitary District

• Purchasing agent for the city of Chicago

• President of the Chicago Civil Service Commission

• President of the Chicago Plan Commission

• City collector

• Cook County civil defense director

• Commissioners of the departments of streets and sanitation, water and sewers, buildings, consumer sales, and weights and measures

• 25 of 66 Cook County circuit court judges

How? Simple. The patronage system.

“I mean, everybody wanted to be a ward committeeman. They knew the power of the patronage system,” former Illinois House Speaker Michael Madigan said in a 2009 interview granted as part of an oral history on Richard J. Daley.

“They wanted a job in the patronage system … I would tell them, ‘Yes, we can put you in a job. But you’re going to work for the Democratic Party.’”

The end of that system ultimately came from the courts. The Shakman Decrees, and decades of court monitors overseeing them, dismantled pure patronage hiring in Chicago and across Illinois.

Indeed, Madigan was the last Irish-Chicagoan political boss. He currently resides in a West Virginia prison, after being indicted on corruption charges.

The machine’s legacy

Chicago’s Irish machine is gone. No longer are tens of thousands of patronage jobs flowing to somebodys-that-somebody-sent.

But two mental models from the machine era remain dominant, and are worth highlighting.

1. There’s a division of the spoils in Chicago government along segregated racial lines. It is common for public officials to claim, in public, that certain elected offices “belong” to one racial group or another, including the city clerk, city treasurer, and powerful City Council committee chairmanships, to name a few. The unfair Irish dominance of public institutions for decades gives license to this behavior, which further divides an already hyper-segregated city.

2. The “where’s mine?” attitude in government persists. Politicians collude with government unions to leverage public resources for the advancement of their own power. Chicagoans see it when collective bargaining agreements with the police union override state law. They see it when 40% of the city’s budget goes toward pensions and debt, a hangover from decades of corrupt deals. They see it when the Chicago firefighters’ union, among others, actively works to make that problem worse. And they see it in the belligerence of Chicago Teachers Union leadership.

This St. Patrick’s Day, it’s worth considering what lawmakers can do to better balance that power, and truly end the machine.

Friendly reminder

Tuesday, March 17, is Election Day in Illinois. Haven’t voted yet? Here’s everything you need to know.

In the news

Whodunit?

I joined Fox32 to discuss why the Chicago Board of Education is wasting money on an investigation into how residents learned of a meeting to hike their property taxes.2

On a related note, the CTU just recorded record-low popularity. Just 27% of Chicagoans have a favorable opinion of the union. Here’s why.

Headlines that can’t happen here

San Francisco Mayor Daniel Lurie is pursuing major changes to his city’s charter, per ABC7:

“This system works for the insider. It’s bred corruption,” Lurie told reporters Wednesday.

If the measures qualify and are approved by voters, they would make significant changes to how San Francisco’s government is structured, how contracts are handled and how future ballot measures reach voters.

“Our city charter has grown so calcified and convoluted that it makes it harder for City Hall to respond to the needs of residents,” said Supervisor Rafael Mandelman, board president. “These measures take a practical approach to modernizing our government to be more accountable to the people it’s meant to serve, while maintaining strong checks and balances.”

Meanwhile, Chicago is the only big city in the country without a city charter.

And in Washington D.C., the City Council is suing the mayor, per the Washington Post:

The D.C. Council sued the mayor last week, seeking to force Bowser to deliver a host of budget documents prepared by agency directors that she has withheld for years —despite city laws, and a recent court ruling, requiring that she provide them.

Mendelson said in an interview Tuesday that the documents are critical to understanding the full scope of financial pressure points or program needs at each city agency, especially in a tough budget year in which cuts and difficult policy trade-offs are on the table.

Still, Mendelson downplayed the legal drama. It was “not a big deal,” he said, and can easily go away if Bowser hands over the documents. “We shouldn’t have to seek a court order,” he said.

Meanwhile, when Chicago’s mayor ignores city laws and the City Council, no one sues.

One reason is that Chicago lacks an independently elected city attorney, as seen in cities like Los Angeles and Columbus.

Another is that if City Council members were to sue the mayor, they would be forced to use the city’s corporation counsel, who reports to the mayor.

Chicago Ald. Mathias “Paddy” Bauler was holding court at his ward headquarters in Old Town.

It was election night, 1964.

Precinct captains queued up to deliver their reports to the boss. A tally board loomed over them, displaying precincts won and lost.

One captain who failed to carry his precinct stood before Bauler, awaiting his fate.

“What kind of a job are you going to look for now?” asked the alderman. The precinct captain slunk away, dejected.

The next captain approached the big board.

“Your brother didn’t vote,” said Bauler.

“My brother didn’t vote!” shouted the captain. “I’ll kill him!”

“Okay,” Bauler said, “bring in the evidence, and you’ll keep your job.”

The Cook County Democratic machine, as described in that story from Milton Rakove’s masterwork “Don’t Make No Waves…Don’t Back No Losers,” no longer exists.

But an underlying truth remains.

With Illinois’ primary elections set for Tuesday, March 17, powerful interests are already tallying your vote. And they have a lot to lose.1

Illinoisans must choose a party ballot when voting in the primary elections:2

• Democrats have a cornucopia of competitive races. I recommend the voting guide from Conor Durkin and Richard Day over at A City That Works.

• Republicans have a meaningful choice in the primary for governor. This piece in the Chicago Contrarian explains why those interested in mounting credible opposition to Gov. JB Pritzker should vote for Ted Dabrowski.

Chicagoans can choose from 51 early voting centers open now through Election Day. You can vote at any one of them. For early vote hours and locations outside of Chicago, click here.

Vote like your brother’s life—or his patronage job—depends on it.

Chicago’s “pay later” political culture was on full display last week.

It started with two credit downgrades on Wednesday, Feb. 25, with Fitch and Kroll each knocking Chicago credit down a notch.

Both agencies pointed to the city’s persistent deficit spending. And disputes between Mayor Brandon Johnson and the City Council.

Kroll made special note of the $11 billion Chicago pension sweetener signed into law by Gov. JB Pritzker last year, following token opposition from Mayor Brandon Johnson’s administration.

But the best example of why Chicago’s credit is sliding toward junk status came to light just two days later, when the Chicago Tribune editorial board revealed a secret, reckless new borrowing plan floated by the Johnson administration.

Here’s what’s happening. And how to stop it.

Johnson’s new borrowing scheme

The Chicago Tribune editorial board revealed Johnson’s administration has been furtively floating a $500 million bond on which the city would make no payments at all for three years.

Not interest-only payments. Literally $0 in payments on the debt.

For the remainder of Johnson’s term, and beyond.

Here’s what the editorial found, specifically:

Wednesday’s downgrades come as the city prepares to solicit bond investors next month for close to $500 million to cover back pay owed to firefighters due to a lengthy contract negotiation and hundreds of millions in anticipated costs to settle lawsuits, most of which pertain to alleged police misconduct. The downgrades will make the debt more expensive for the city, as investors will be expected to demand higher yields in response to the higher risk tied to Chicago’s precarious financial condition.

But here’s the real shocker: The city is structuring this debt so it doesn’t have to make payments for the next three-plus years, extending the time frame for paying off the bonds and making the entire enterprise considerably more expensive than was envisioned during the fraught budget discussions late last year.

In short: Johnson gets to spend the money now. But the next mayor—and the next generation of Chicagoans—are stuck with the tab.

Johnson’s bait-and-switch

This backloaded payment structure is not what Johnson’s team sold to City Council members last year.

Back in November, Chicago CFO Jill Jaworski briefed the Council on a borrowing package that included new debt to cover, among other items, retroactive raises for firefighters.

Ald. Bill Conway wisely kept receipts on that briefing. Borrowing for this kind of operating expense in itself is a terrible financial practice. But as Conway noted, at least the payment schedule was relatively straightforward.

As we know now, that was all a bait-and-switch.

It’s happening again

This isn’t the first time Johnson has dumped a massively backloaded repayment schedule on the backs of young Chicagoans.

Last year, the mayor broke a tie vote on an $830 million bond deal that made no payments at all for two years (again, through the remainder of his term) and no payments on the principal for 18 years after that.

This ballooned the total cost of that borrowing to $2 billion.

At the time, I dubbed it Johnson’s parking meter deal.

In research for our book The New Chicago Way: Lessons from Other Big Cities, my co-author Ed Bachrach was fortunate to interview the late Dick Ravitch. Ravitch is arguably the single person most responsible for saving New York City from bankruptcy in the 1970s, among many other achievements throughout his career in public service.

In Ravitch’s book So Much to Do, he wrote, “Cities need access to the credit markets for two reasons that are respectable and one that is not.”

The first respectable reason is short-term borrowing to balance emergency mismatches of revenue and spending in a given year, due to an economic shock, for example. The second respectable reason is to borrow in the long term to fund capital projects.

The third reason, which is not respectable, is to cover operating deficits. That is exactly what Johnson—and mayors before him—have done.

How can Chicago stop this?

City Council should be calling public hearings and demanding answers on Johnson’s new borrowing package.

The extent of their authority to stop the deal already in progress remains murky, but vocal opposition from the Council could give the bond market pause.

Beyond the short term, Chicago governance is riddled with shortcomings that make the city vulnerable to bad deals like this, including:

• Lacking an independently elected CFO with real authority, as is common in other big cities.

• Lacking a requirement for voters to approve new debt, as is common in other big cities.

• Lacking a fully resourced budget office within the City Council.

• Lacking an independently elected city attorney. (Today, if the Council wanted to sue the mayor’s office, they would be required to use corporation counsel…which reports to the mayor’s office.)

Many of these safeguards are typically found in a city charter. But Chicago is the only big city without one.

In the news

Pesca podcast: I joined the great Mike Pesca on his podcast Not Even Mad alongside The Bulwark’s Andrew Egger. We discussed the State of the Union address, tariffs, and the Department of War’s treatment of Anthropic. (Apple, Spotify).

Charter chatter: The leader of the nonprofit legal team that brought down Trump’s emergency tariffs at the Supreme Court penned an op-ed in the Chicago Tribune about why constitutional limits matter, and why we should have them here in Chicago via a modern city charter (“Sara Albrecht: What Chicago can learn about the separation of powers from the Supreme Court tariff ruling”). Also worth noting: Newly announced Chicago mayoral candidate Liam Stanton includes a city charter in his platform.

The Chicago City Council is like no other. Just ask the man holding the gavel.

“Chicago is unique in that the mayor, the executive, also presides over the legislative branch,” Chicago Mayor Brandon Johnson told Twitch streamer Hasan Piker last week.

“Don’t get any ideas you all. That’s working for me.”

This is an unprecedented remark for a Chicago mayor to make. And it’s correct on two counts.

First, Chicago government is unique in granting the mayor so much authority over City Council. No other big city works this way.

Second, the structure does work well for the sitting mayor. And the interests who have the mayor’s ear.

But it doesn’t work well for Chicago.

The freakish power of Chicago’s mayor

When Johnson calls full City Council meetings to order, he bangs a custom gavel engraved with his name, two Bible verses,1 and two words: “Stay Strong.”

The flourish is fitting.

Chicago stands alone, according to a new analysis from the Chicago Policy Center.2 It is the only big city in the country where the mayor has the power to preside over the council directly, and the power to veto its output.

In cities that put real executive authority in the mayor’s office—as opposed to a council-manager form of government—it is common for the city council to elect its own speaker or president to preside.

The only exception, aside from Chicago, is Houston. But the mayor of Houston does not enjoy veto power.3

Presiding over City Council isn’t the only way the executive dominates the legislative branch in Chicago. Consider a few others:

• Chicago is the only big city where the mayor directly fills council vacancies. This empowers the mayor to trade appointments for votes, often resulting in family political dynasties, such as the new Burnett dynasty in the 27th Ward.

• The prevailing norm is that the mayor appoints committee chairs, creating an inherent conflict-of-interest when committees are supposed to oversee executive-branch operations.

• The mayor’s office dominates the budget process. Check out this great new primer from the Civic Federation on how that played out during the budget fight last year.

Taken together, these structural features make City Council less a check on the fifth floor than an extension of it.

How to change the dynamic

“Who presides over the council?” is a basic governance question. The answer typically rests in city charters.

But Chicago is the only major city in the country without a charter. So these rules live in state law. Per the Illinois Municipal Code: “Mayor presides. The mayor shall preside at all meetings of the city council.”

Booting the mayor from City Council will require help from Springfield.

Aldermen should ask for it.

In the news

Praise for The Last Ward: I was honored to see The Last Ward cited in a new report on Chicago’s media ecosystem published last week by researchers at Northwestern University’s Medill School of Journalism. Thank you all for your readership, feedback, and action.

High-ranking Democrat calls for Illinois to opt-in to federal scholarship program: Two weeks ago we urged Illinois Democrats to unlock more than $100 million for Chicago students by opting-in to the federal tax credit scholarship program. Last week, Comptroller Susana Mendoza became the highest-ranking Illinois Democrat to call for the same. Her op-ed supporting the program in the Chicago Tribune is a must-read: “Susana Mendoza | Put Illinois students above politics, and opt in to the federal scholarship program.”

Update to the treasurer-boycotting-treasuries controversy: The Chicago Tribune’s Alice Yin ran an important follow-up story on the Chicago treasurer’s boycott of U.S. treasuries. In short: city portfolio managers warned Treasurer Melissa Conyears-Ervin that announcing a boycott of U.S. treasuries would call their fiduciary duty into question. But Conyears-Ervin did it anyway. Readers of The Last Ward know why the city treasurer is a waste of an elected office, and how Chicago can reform it.

Illinois primary season is in full swing, with Election Day just a month away.

The political shakeup is unprecedented in the Chicago area.

Five open congressional seats, plus an open seat for U.S. Senate, several open seats in the state House and Senate, and a competitive race for Cook County board president.

All will largely be decided by the March 17 Democratic primary.

And the latter saw one of the most interesting developments of any race last week, with news of an auspicious endorsement. Or lack thereof.

‘Didn’t seek’ endorsement from the Chicago Teachers Union

The Chicago Tribune’s Alice Yin reported that Cook County Board President Toni Preckwinkle did not seek an endorsement from the Chicago Teachers Union.

“I didn’t seek their endorsement,” Preckwinkle told reporters Thursday, before rattling off a list of unions like the Chicago Federation of Labor and other left-leaning groups who are backing her campaign. “And I’m proud of those endorsements,” she said. “I’ve also been endorsed by the governor of the state, JB Pritzker, the speaker of the House and the president of the Senate…”

[T]he former public school teacher’s choice to skip the CTU’s endorsement slate, which has long been viewed as an early signal to progressives about which candidates they should coalesce around, was striking.

Under heavy fire from political opponents, the union and its close ally Johnson have been struggling to hold together their coalition that got him elected in 2023 after backing Preckwinkle for her 2019 mayoral bid. That’s led a few on the left to jump ship early, as evidenced in the mayor’s grueling budget fight last fall.

But it’s unclear whether the famously tight-lipped Preckwinkle is actually on the outs with CTU or merely distancing herself out of concern that the firebrand group’s brand — or Johnson’s — has grown toxic. Preckwinkle is in the midst of one of her most heated primaries yet, and moderate challenger Ald. Brendan Reilly has been attacking her early support of Johnson as being instrumental to his rise.

Preckwinkle, head of the Cook County Democratic Party, is the most prominent Illinois Democrat to snub the union in this manner.

And it’s happening even as CTU-backed Mayor Brandon Johnson is touting his support for Preckwinkle’s campaign. (A fact quickly highlighted by her opponent, Chicago Ald. Brendan Reilly.)

So what’s really happening here?

Gates’ laundry list of controversies

The union’s influence has waned in part due to an endless string of controversies from CTU President Stacy Davis Gates.

Here’s the comprehensive list, with receipts, in no particular order.

• Threatened a principal and former CTU delegate with physical violence

• Insulted critics as “slow”

• Mocked Chicago Public Schools CEO Pedro Martinez by comparing him to a “terrible” special education student who can’t be suspended

• Called a prominent local journalist a “stalker” for reporting on her actions as union president

• Told a senior SEIU executive: “Y’all ain’t shit and you ain’t shit”

• Hid five years of union audits from CTU members and then bullied teachers who were forced to file a lawsuit to see those audits, calling them “extreme right wing” and claiming they were associated with Project 2025

• Called the Chicago Tribune “bullshit” and the Illinois Policy Institute “freak shows”

• Killed a school choice scholarship program that served thousands of low-income Chicago children, including several who attended the same private school as her own child.

• Took an illegal property tax break on a home in Indiana

• Failed to pay $5,700 in city trash, sewer, and water bills despite making more than $289,000 a year

• Improperly funneled CTU member dues into Brandon Johnson’s campaign for mayor, forcing teachers to file an unfair labor practice complaint

• Pulled CPS students out of class for the explicit purpose of voting “yes” on the “Bring Chicago Home” referendum, in clear violation of CPS ethics rules

• Pushed for a $300 million high-interest payday loan to fund a new CTU contract

• Spurred local and national backlash after claiming standardized testing is “junk science rooted in white supremacy”

• Fought for lower property taxes on CTU headquarters while advocating for higher taxes on others

Her actions and ideological extremism have come with compounding costs for the union’s political muscle.

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No longer winning

Has CTU’s pull really weakened since Johnson went from the union’s payroll to occupying the fifth floor of City Hall?

Consider the following:

1. Voters rejected the CTU-backed Bring Chicago Home referendum in a low-turnout election that should have favored the union and Mayor Brandon Johnson.

2. Gates claimed supporters of a bill in Springfield to protect against closure of selective enrollment CPS schools were “racist.” The bill then passed the Illinois House 92-8.

   1. The bill, filed by state Rep. Margaret Croke, D-Chicago, was inspired by fears that a CTU-dominated school board would close or significantly alter selective enrollment schools. It would have barred CPS from any school closures until a fully elected board was seated in 2027. “That kind of criticism is uncalled for,” Gov. JB Pritzker said in response to the union’s attack. “Especially about the bill that was being discussed and about the person that was leading that bill.”

3. Six of 9 CTU-backed candidates lost their elections for Chicago Board of Education. The union spent $2.1 million on losing candidates, according to a Chicago Policy Center analysis.

4. Polling in 2025 showed the union’s favorability underwater for the first time in modern Chicago history. Just 29% of Chicagoans had a favorable opinion of the CTU while 60% had an unfavorable opinion (-31 net). Asked about Gates, 18% had a favorable opinion while 55% had an unfavorable opinion (-37 net).

It’s tough to come to any other conclusion: voter attitudes toward the CTU have shifted dramatically.

What to watch for

In 2026 and beyond, the following will tell the tale on whether CTU remains toxic with Illinois Democrats:

• The results of competitive March primary elections in which CTU has endorsed a candidate. Keep a special eye on state Rep. Jaime Andrade’s race in Chicago. He is the union’s top target to take out in the Illinois House. CTU is backing democratic socialist challenger Miguel Alvelo-Rivera.

• What, if anything, the Gates-led Illinois Federation of Teachers is able to pass in Springfield during the spring session. The IFT is running a lobby day this week to pressure state lawmakers to pass a suite of new tax hikes.

• The results of the November 2026 Chicago school board elections, in particular the citywide election for school board president.

• Whether Illinois state lawmakers pursue reforms to reduce the CTU’s extraordinary power over Chicagoans.

Depending on the results of these upcoming fights, Preckwinkle may be far from the last prominent Democrat to avoid a CTU endorsement.

In the news

Reminder: I’ll be joining Paris Schutz and the Chicago Area Public Affairs Group at the Union League Club on Feb. 19 for a discussion on the Illinois primaries. The event is sold out, but you can join the waiting list here.

I joined The Mincing Rascals on WGN to discuss the SAVE Act, ICE, and more. (YouTube, Spotify, Apple Podcasts)

My “green light” recommendation: Trances (1981).

A new program could unlock hundreds of millions of dollars for education in Chicago and across the state.

But it’s at risk of becoming a political football in Illinois, where special interests are trying to kill it before a single student can benefit.

In this week’s edition of The Last Ward, we break down that program, including my Chicago Tonight debate on whether Illinois should participate, and how you can take action to help bring it home.

How does it work?

The new program is called the Federal Scholarship Tax Credit, or FSTC. And it was established by the Educational Choice for Children Act, which Congress passed last year.

Here’s what you need to know about FSTC:

• Americans can donate $1,700 to an eligible charity focusing on education and get $1,700 back on their federal tax bills.

• These charities can cover education expenses for students attending public, private, or home schools.

  • Expenses include tutoring, special needs services, books, supplies, tuition and more.

• Most states (28 of 50) have already opted in to the program, hoping to hit the ground running when FSTC goes live in 2027.

If Illinois opts in, charities serving Illinois students can rake in donations that trigger the federal tax credit for donors.

If Illinois opts out, every Illinoisan will still be able to access the $1,700 tax credit. But they can only get it if they donate $1,700 to charities elsewhere.

In other words, dollars that could go toward helping Illinois students will instead flow to other states and Washington, D.C.

That’s why Democratic Colorado Gov. Jared Polis told the Colorado Sun he “would be crazy not to“ opt in to the program, and went deeper into his reasons for opting in on a recent podcast interview.

Polis on why he supports the program:

I think it’s great because it drives more donations to Colorado charities that serve kids. Some donors will choose charities that you and I might like. Others will choose some we don’t like. But there’s going to be a lot of good, because they have to use 90% of the money on direct benefits for kids…90% of the money has to go right out the door to kids in a variety of ways: after-school programs, tutoring, summer school, scholarships, all of those kinds of things.

On the funding model:

This encourages creativity. The feds are paying for it. It’s free money from our state perspective … it definitely will cause a big influx of funding for a lot of nonprofits that are doing great work with kids.

On filling in gaps for public schools:

Music programs, performing arts, all of those kinds of things often suffer from lack of resources because when districts have to make tough decisions they often say, well, we gotta do the academics and we don’t need to do the enrichment. Well the enrichment is very important. And this can help fund some of those activities outside of normal school hours.

Polis is right. Leaders in Chicago and Illinois should take note.

How this helps Chicago and Illinois

I joined Chicago Tonight for a debate on whether Illinois should opt in. You can watch it on YouTube and X.

My opponent was speaking on behalf of the League of Women Voters of Illinois, which signed a letter opposing the program alongside groups like the Illinois Federation of Teachers (currently led by Chicago Teachers Union President Stacy Davis Gates.)

Below are my three main points in favor of the program—none of which were rebutted in the debate or the letter.

1. Boosting the booster clubs

Chicago is home to more than 600 public schools, and hundreds of booster clubs and sister organizations to support them. There’s also a tapestry of nonprofits supporting the public school system as a whole. If Illinois opts in, many of these nonprofits will be able to offer donors a dollar-for-dollar federal tax credit in exchange for supporting their work. If 10,000 Chicagoans take advantage of the maximum $1,700 tax credit to fund these extra resources for public school kids, that’s $17 million, or $170 million over 10 years.

2. Less money for DC. More money for Chicago students.

The more you oppose the Trump White House, the more you should support this program. It allows a donor to take $1,700 that would otherwise go to Washington, D.C. and use it to support their local school community, including public schools. Ironically, many of the same groups that signed the letter demanding Pritzker opt out of the program have lamented the fact that Illinois sends more money to Washington than it gets back.1 The FSTC program helps recoup some of that money.

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3. Protecting underprivileged students

The coalition letter demanding Gov. JB Pritzker opt out cited concerns about funding tuition for private schools that do not provide adequate protections for LGBTQ students, English Language Learners, and students with special needs.

There are two problems with this argument.

First, the concern specifically about LGBTQ students rings hollow given that Polis, a champion of opting in, is the first openly gay person elected governor in U.S. history.

Second, opting out would incentivize Illinoisans to send more charitable donations into states that lack the same protections Illinois students enjoy. Opting in means keeping more of those dollars here at home.

How to get it done

Illinois can opt in to the program in one of two ways.

1. The General Assembly passes a bill that Pritzker signs.

2. Pritzker issues an executive order.

The first option took a major step forward last week when state Sen. Adriane Johnson, D-Waukegan, introduced an opt-in bill (Senate Bill 3776).

If you support opting in, contact your state senator and tell them to support SB 3776 here.

Pritzker has not committed to opting in. But he has not committed to opting out, either.2

In the news

I joined Fox32 Chicago’s ChicagoLIVE program to discuss the Chicago Teachers Union’s recent audits controversy and Chicago’s drop in violent crime.

Reminder: I will be joining Paris Schutz and the Chicago Area Public Affairs Group at the Union League Club on Feb. 19 to discuss Illinois’ upcoming primary elections. Tickets here.

As predicted, cracks are already forming in the budget passed by Chicago City Council late last year.

Crain’s Chicago Business reported last week that Chicago municipal bonds have moved sharply against the broader market.

Chicago has “gone in completely the opposite direction of the market as a whole” since the start of 2026, according to University of Chicago municipal finance expert Justin Marlowe. Investors are demanding higher returns to hold Chicago debt even as borrowing costs ease elsewhere.1

Unlike many other big cities, Chicago’s greatest challenge has nothing to do with its land, the environment, talent, or basic infrastructure.

Chicago’s greatest challenge is its horrific financial situation, which came about due to decades of poor decisions.

Here’s the good news: that is a manmade problem. The solutions are manmade, too.

So how can the current mayor, or the next one, ensure the city starts making better decisions?2

Chicago’s financial freefall

Chicagoans should be wary of politicians who talk a good game on financial stability, but are unwilling to tackle the uncomfortable conversations needed to get there.

That starts with honesty about where the city stands today. Here are the lowlights:

• Chicago holds more pension debt as a city than 44 of 50 U.S. states ($53 billion)

• Seven of the 10 worst-funded pensions in the nation are in Chicago.

• More than 40% of all city spending goes toward debt and pensions. That’s the highest share of any big-city budget dedicated to fixed costs by far, according to S&P Global.

• Chicago commercial property owners shoulder the highest property taxes in the nation. But more than 80% of the city’s property tax levy goes straight to pension costs—not services.

• Chicago Public Schools is the largest municipal issuer of junk bonds in the nation.

While growing the city’s economy is the best way to solve these problems—see the Chicago Abundance Agenda for ideas—that is simply not enough on its own. And unlocking more growth itself requires reforms to reduce Chicago’s government debt, which is currently repelling business investment.

Below are five things Chicago Mayor Brandon Johnson could do to right the ship.

But based on his performance thus far, Johnson is unlikely to pursue any of these.

So candidates for his job in 2027 should take note.

1. Stop digging: No more pension sweeteners

The first step to getting out of a hole is to stop digging. But Chicago refuses to stop.

Chicago police and fire already have among the worst-funded pensions systems in the country. But new pension sweeteners for Chicago police and fire passed the Illinois General Assembly with barely a peep from the mayor’s office last year—adding $11 billion in new liabilities and dropping the funds to just 18% funded after the governor’s signature.

Chicago CFO Jill Jaworski wrote to the governor’s team that the bill would make Chicago’s police and fire pension funds “technically insolvent.” But that was after it had already passed the General Assembly. The governor signed the bill anyway.

Kudos to Illinois Comptroller Susana Mendoza for being the only prominent public official to speak out against these extraordinarily irresponsible sweeteners.

Every candidate for public office in Chicago should commit to a simple promise: no more pension sweeteners.

2. Advocate for allowing Chapter 9 bankruptcy

Chicago is the only big city in the country that cannot restructure its debt in federal bankruptcy court.

Without the option of Chapter 9 bankruptcy, city government is increasingly becoming less of a service provider and more of a collection agency that transfers wealth from the young to the old—until the city reaches a breaking point.

Note that the mayor doesn’t need to argue for entering bankruptcy. Simply having the tool on the table forces honest conversations with government-worker unions and other stakeholders. It could even help with renegotiating the city’s notorious parking meter deal.

Allowing the city to enter Chapter 9 requires a change in state law. The mayor will need to advocate for it. But the debt crisis unfolding in nearby Harvey, Illinois, offers a rare opportunity for Chicago leaders to proactively shape that legislation in Springfield.

3. Improve financial oversight

As the most recent budget fight illustrated, Chicago is not equipped to implement structural changes in its budget, make good budgeting decisions, or even independently analyze the numbers outside of the mayor’s office.

The mayor should advocate for:

• Creating an independent budget office a la New York City.

• Filling the legally required position of city administrator, which could help implement the budget and lead a zero-base budgeting process.

• Changing the responsibilities of the elected city treasurer to be more like a CFO or comptroller, based on similar offices in New York, LA, and Houston.

All of these measures are common in other big cities.

Every large American city lays out these checks and balances in a voter-approved city charter. But not Chicago. Chicago is the only big city in the country without this governing document.

Chicago’s lack of a city administrator is one glaring example of why a charter is so necessary. Without a city constitution, Chicago mayors have been able to ignore filling this critical position since 1954, despite the Municipal Code of Chicago demanding the mayor “shall appoint” the officer, who must then be confirmed by City Council.

4. Empower voters to approve tax hikes and new debt

Chicago will likely need some form of new revenue to right the ship.

But lawmakers should have to make the case for tax hikes and new borrowing directly to voters, as they do in other big cities.3

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In theory, Chicagoans already have far more authority over property tax hikes than it appears. But due to a TIF loophole that allows hundreds of millions of dollars in higher property tax collections for Chicago Public Schools without getting voter approval, voters rarely get a say on new taxes.

5. Follow the EY recommendations

The Johnson administration ignored $1 billion in structural savings identified in EY’s analysis of the city budget last year.

Chicago should implement 100% of the recommendations identified in the EY report.

In the meantime, the city should commission deeper analysis on each of the report’s subject areas, with findings presented to the City Council in open hearings.

Changing course

Chicago’s greatest challenge is not a lack of natural resources. Nor top-tier universities. Nor basic infrastructure.

It is the compounded effect of decades of poor financial decisions.

A better path is possible.

Mayoral candidates have a unique opportunity to chart that path, and win on a mandate to execute against it.

In the news

Last week I joined Chicago-bred entrepreneurs Ravin Gandhi and Al Goldstein on their podcast Forged in America for a wide-ranging conversation on the challenges facing Chicago and solutions that the next mayor should pursue (YouTube, Spotify, Apple Podcasts).

I also joined the Mincing Rascals podcast on WGN to discuss the Border Patrol shooting of Alex Pretti in Minneapolis, the race for Dick Durbin’s Senate seat, and more (YouTube, Spotify, Apple Podcasts).

My “green light” recommendation ahead of the Winter Olympics: White Rock (1977).

Reminder: I will be joining Paris Schutz and the Chicago Area Public Affairs Group at the Union League Club on Feb. 19 to discuss Illinois’ upcoming primary elections. Tickets here.

It’s been one year since Chicago Inspector General Deborah Witzburg dropped a bombshell report revealing Mayor Brandon Johnson’s office had accepted hundreds of gifts—including Hugo Boss cufflinks, Gucci handbags and premium whiskey—without properly reporting them as required by the city’s ethics ordinance.

The headlines were, predictably, spectacular.

Designer handbags! A mystery gift room! The mayor blocking investigators from entering!

And that’s exactly the problem.

Welcome to what I’ve dubbed “Gift Room Syndrome“—when a dramatic scandal is so theatrically absurd that Chicagoans miss the deeper, more troubling lesson hiding in plain sight.

As I wrote when this first broke, the infamous gift room scandal was never really about Brandon Johnson hoarding luxury goods for his personal benefit.

The real scandal—the one that should concern anyone who cares about Chicago’s future—is what the scandal revealed about how our city government is structured.

What actually happened

Here’s the gift room story most Chicagoans know: The mayor accepted fancy gifts. The Inspector General tried to investigate. The mayor’s office blocked access to a “gift room” where the items were supposedly stored. Eventually, Johnson released a 22-second video showing shelves of mostly unremarkable trinkets.

Here’s what many people don’t know: The gift room didn’t even exist when investigators first tried to inspect it.

In November 2025, Witzburg revealed the closet-sized room Johnson’s office eventually showed to the press wasn’t constructed until February 2025—after she first attempted an unannounced inspection.

Let that sink in. When the IG first tried to see where gifts were stored, there was no gift room. City lawyers blocked her from entering. Then the mayor’s office built one and acted like it had been there all along.

As Witzburg put it: “We or anybody else has no way of knowing, in an independent, confirmed way, what exactly was happening with that city property before the new gift room was built.”

The mayor’s office blocked the IG’s access not once, but twice. The second attempt, involved investigators trying to inspect a city office where they believed gifts were improperly stored. Again, Corporation Counsel lawyers intervened to prevent the inspection.

And those public tours Johnson promised? According to the mayor’s spokesperson, exactly two people signed up. Neither showed up.

What the gifts revealed

The gift room fiasco exposed a systemic breakdown in oversight and accountability—a pattern that Witzburg called the mayor’s “hostility to oversight.”

But it’s deeper than that.

Consider what actually happened: For decades preceding the Johnson administration, when it came to recording and storing gifts to the city, Chicago mayors operated under an “unwritten arrangement” with the Board of Ethics that allowed them to completely ignore the city’s own Government Ethics Ordinance.

That ordinance required prior approval of many gifts, reporting to the Board of Ethics and reporting to the city comptroller. But Chicago mayors ignored all of that. Instead, they kept a logbook somewhere on the fifth floor that the public could theoretically request to see.

When the IG tried to verify that this “public” log was actually accessible, mayoral staff denied the request and told them to file a FOIA instead. Then the mayor’s office simply ignored the FOIA.

Only when the IG issued a formal investigative request did the administration produce the log—revealing hundreds of undocumented gifts, many from unknown donors.

Then, when investigators tried to physically inspect where these gifts were stored, the city’s Corporation Counsel stepped in to block them.

The pattern shows deliberate obstruction of the city’s own watchdog.

A pattern of obstruction

The gift room fits into a broader pattern of the Johnson administration’s approach to oversight. In February 2025, the Inspector General issued a memo accusing the Law Department of “selectively” opposing OIG investigations when they “may result in embarrassment or political consequences to city leaders.”

The memo detailed how Corporation Counsel has:

• Withheld city documents based on dubious attorney-client privilege claims

• Demanded to sit in on OIG investigative interviews

• Delayed enforcement of OIG subpoenas

This is the same Law Department that, under previous leadership, fought to withhold the Laquan McDonald video until a court ordered its release. The same department that in the gift room case was, as the IG’s report put it, “apparently representing the mayor in opposition to the OIG.”

That phrase—”representing the mayor in opposition to the OIG”—gets to the heart of Chicago’s governance problem here. The Law Department is supposed to represent the city and the public interest. Instead, it operates as the mayor’s personal defense firm.

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As I detailed in April, Johnson has not led the passage of a single piece of anti-corruption legislation during his time as mayor—until the gift room scandal forced his hand. He actively blocked other elected officials’ efforts, from killing an ordinance restricting lobbyists’ political giving to refusing to recuse himself from negotiations with his former employer and largest campaign contributor, the Chicago Teachers Union.

Gift Room Syndrome in action

This is where Gift Room Syndrome kicks in. The more dramatic the story—designer handbags! hidden closets! mystery donors!—the less likely residents grasp the most important lesson.

Chicago saw this play out with the recent investigation into how the public learned about the Chicago school board’s plan to hike property taxes over the Christmas holiday. The headline was Onion-esque: Mayor uses property taxes to investigate how residents learned of higher property taxes.

But the real scandal wasn’t the investigation into the “leak.” It was that Chicagoans should have been voting on an extra $550 million in property tax revenue flowing to CPS this year—but never got that vote, thanks to the TIF loophole that allows the city to subvert the state’s property tax cap.

It’s the same dynamic: A dramatic surface story obscures deeper systemic failure.

Why obstruction of oversight matters

Chicago faces serious challenges that will require a combination of cutting some spending, slowing the growth of other spending, and raising new revenue of some kind—whether for schools, infrastructure, or basic services.

But raising new revenue requires public trust. And public trust requires accountability.

This is one reason Johnson’s “Bring Chicago Home” referendum failed. Voters rejected the real estate transfer tax increase in large part because the administration wasn’t transparent about how the money would be spent. When government actively blocks oversight, it poisons the well for any future ask.

As Inspector General Witzburg said: “My fear is that what we are seeing here is less about the cuff links and the size 14 men’s shoes, and it’s more about hostility to oversight.”

When the mayor’s office can ignore ethics ordinances through “unwritten arrangements,” block the Inspector General from doing her job, deploy city lawyers to protect political interests over public accountability, and face zero consequences—the system is designed to avoid scrutiny rather than enable it.

The structural problem

Here’s what the gift room scandal revealed: Chicago lacks the basic structural safeguards that prevent this kind of dysfunction in other major cities.

The Corporation Counsel is appointed by the mayor and serves at the mayor’s pleasure. When the IG tries to investigate the mayor’s office, the mayor’s own lawyers block the investigation. This is by design.

Other big cities have a different approach:

• In Los Angeles, Columbus, and San Francisco, the city attorney is elected independently.

• In San Antonio and Austin, the city attorney is appointed by and reports to a city manager who is accountable to the city council.

• In San Jose, the city attorney is appointed by and reports directly to the city council.

Chicago also lacks meaningful protections for its Inspector General. When Witzburg tried to inspect city premises—as she is explicitly authorized to do under city ordinance—the Law Department simply said no.

To her credit, Witzburg fought back. In February 2025, she asked the City Council to pass protections preventing this kind of interference. Ald. Matt Martin introduced an ordinance to do that.

After months of negotiations, the ordinance passed in July 2025. The final version was a compromise—it restricts when Law Department lawyers can attend investigative interviews and limits improper attorney-client privilege claims, though it removed provisions on subpoena enforcement that Witzburg had sought.

Still, as Witzburg said after passage, the ordinance represents “a tremendous step toward aligning Chicago with national standards and federal law on independent oversight.” It took the gift room scandal, public pressure, and Witzburg’s willingness to fight, but the reform happened.

This raises a question: Does one hard-won ordinance, passed only after intense public scrutiny of the gift room debacle, fundamentally change the structural problems here?

What reform actually looks like

If Chicago is serious about preventing future gift room scandals—and the deeper accountability failures they represent—the city needs structural reforms:

1. Strengthen OIG protections further

The ordinance passed in July 2025 was a good start, but it was a compromise. The final version removed provisions on subpoena enforcement that the IG had sought. Chicago should continue building on this progress to ensure the watchdog has full enforcement power without Law Department interference.

2. Elect the Corporation Counsel, or take it out of the mayor’s office

An independently elected city attorney would owe their loyalty to voters, not the mayor. They could provide actual oversight instead of political protection. This is how Los Angeles, Columbus, San Diego and San Francisco operate. Short of making the corporation counsel an elected position, the role could report to a city administrator—a position that is actually supposed to exist in Chicago. As Ed Bachrach and I noted in 2021, Chicago’s Municipal Code requires the mayor to appoint an administrative officer (essentially a city manager) who must be confirmed by the City Council. This position, created in 1954, is designed to “supervise the administrative management of all city departments” and provide coordination across agencies. But no mayor has bothered filling it since Jane Byrne. Reviving this long-dormant position—and having the corporation counsel report to it rather than directly to the mayor—would help create the independence necessary for real oversight.

3. Create enforcement mechanisms through a city charter

The gift room scandal revealed that Chicago’s ethics ordinance was effectively optional. Decades-long “unwritten arrangements” allowed officials to simply ignore requirements.

Chicago should follow other big cities’ practices of establishing a city charter with regular charter revisions—empowering civic leaders to thoroughly review and update governance structures that can’t be waived through backroom deals.

A proper city charter, approved by voters, could create real accountability through:

• Clear procedures for ethics compliance that can’t be waived by informal agreements

• Independent ethics enforcement with real penalties

• Legal standing for citizens to sue the city into compliance when officials violate charter provisions

4. Consolidate inspector general offices

Chicago has five different IGs (city, CPS, CHA, Park District, City Colleges) with wildly different powers and funding. Consolidate them under one roof, like New York’s Department of Investigation, with consistent authority and resources.

5. Overhaul the Board of Ethics

The current board enabled the “unwritten arrangement” that allowed gift room syndrome to fester for decades. Chicago should follow New York’s model of a Conflict of Interest Board with real training, enforcement, and investigative capacity.

One year later

It’s been 12 months since Chicago learned about the gift room. The mayor’s office has released new guidelines. There’s an online gift log now. And you can sign up for a tour.

But the fundamental problem remains: Chicago’s governance structure actively works against accountability. The mayor controls too much. Independent oversight is too weak. And when watchdogs try to do their jobs, the mayor’s own lawyers stop them.

Gift Room Syndrome strikes when we let the dramatic details distract us from that reality.

The question one year later isn’t whether Johnson will accept more questionable gifts. The question is whether Chicago will finally build a government where oversight works regardless of who sits in the mayor’s office.

Until the city addresses that structural failure, Chicago will keep stumbling from scandal to scandal, outrage to outrage, always focused on the symptoms while the disease spreads.

Chicago deserves better than government by “unwritten arrangement.” We deserve a charter that can’t be ignored, watchdogs that can’t be blocked, and accountability that doesn’t depend on the mayor’s good graces.

The gift room’s first anniversary is as good a time as any to demand it.

In the news

Early voting across Illinois begins soon for the March 17 primary elections.

For a deeper discussion on those elections, I’ll be joining the Chicago Area Public Affairs Group at the Union League Club on Feb. 19.

Members of the general public can buy tickets here.

Sometimes the little guy wins.

It happened on Friday, Jan. 16, when leadership at the Chicago Teachers Union published financial information that they had kept hidden for years.

The CTU’s internal bylaws require leadership to produce an audit for members every year. But the last audit ever shown to members was posted Sept. 9, 2020.

So members concerned with basic transparency—especially as the union transformed into the city’s largest political spender and Mayor Brandon Johnson’s top financial backer—had been demanding to see those audits ever since.

In return, those members endured lies and bullying from CTU leadership.

But their persistence paid off.1

The newly published audits reveal several inconsistencies in union reporting that may have led to misstatements to members and the federal government, according to information published exclusively by The Last Ward.

Members demanding transparency were right all along

CTU members saw something new when opening up their member portal on Friday.

The website now hosts 11 audits members have never seen before. And the content of those audits suggest several reasons why leadership may have kept them hidden for so long.

Before getting into those specifics, it’s important to note union leadership has repeatedly claimed that members already had access to these documents.

“The reality is that the union has always shared its audits with its members,” CTU attorney Robert Bloch told The Intercept in a story published before the weekend.

But members had never seen the 11 audits posted Friday.

As CTU leadership attempts to spin the news surrounding the release of these audits, observers should keep that misdirection in mind.

Stacy Davis Gates appears to be misrepresenting union finances

The new filings appear to show that while CTU told a court and its membership that the audits were not yet complete, union leadership suggested the opposite to the U.S. Department of Labor and IRS.

In other words, CTU President Stacy Davis Gates might have been telling the truth about the audits to CTU membership, a Cook County judge, the IRS or the Department of Labor.

But she could not have told the truth to all four.

Here’s why:

• Fed up after years of stonewalling, members filed a lawsuit against the CTU on Oct. 8, 2024, demanding release of the audits. They are represented by the nonprofit litigation firm Liberty Justice Center.

• As part of the case, CTU President Stacy Davis Gates declared in court that “in recent years, CTU has been catching up on finalizing audits after 2019,” so the audits for 2020, 2021 and 2022 were not “ready” until December 2024.

• Further, the audits for 2023 and 2024 were not completed until 2025, according to documents released by CTU on Friday.

During the same time period Gates told the court the union had not finished a review of their books, she was submitting reports to the Department of Labor and IRS suggesting the opposite.

Look at the union’s 2022 LM-2 filing with the Department of Labor, for example. One question asks whether the union had an audit or review of its books conducted by an outside accountant. Gates marked “yes.”

Gates was also telling the IRS that audits had been procured, according to tax filings prepared by the CTU Foundation. Each year, Gates reported on the Foundation’s Form 990 that the foundation obtained independent audits.

Here’s an example from the CTU Foundation filing for the 2022 fiscal year.

If CTU was indeed years late in conducting an independent review of union financials, it appears Gates was filing inaccurate reports with the federal government. Alternatively, if CTU actually did procure those audits in a timely manner, but later changed or reproduced the audits to read differently, Gates was misleading the court and her members.

Which is it?

The stakes are high.

Making a false statement under oath in Illinois is a Class 3 felony. Making false statements on the LM-2 would make the signatory subject to criminal penalties for false reporting and perjury. And making false statements on the Form 990 could lead to a loss of the Foundation’s tax-exempt status, and in extreme cases, criminal penalties.

The union kept two sets of books

The audits released Friday also reveal the union commissioned audits each year for two different financial statements.

It’s important to understand the difference:

• The “combined” financial statements include the union and its two PACs. These were the topline financials reported to members for the last several years, without the associated audit materials the union had previously included in its reporting to members.

• The “consolidated” financial statements include the union, its two PACs, and the CTU Foundation.

Notably, the union failed at least two audits for the combined financials (fiscal years 2021 and 2024). Those audits contain adverse opinions, which mean the auditor concluded CTU’s financial statements were misstated in a material and pervasive way.

“Management has elected to omit the activities of the Chicago Teachers Union Foundation, Inc. and the Children and Teachers Foundation of the Chicago Teachers Union,” the opinion reads.

As a result, the combined financial statements “do not represent fairly the financial position of the Chicago Teachers Union,” the auditor found.

Hiding the foundation financials in this way should raise concern for members and warrants further investigation.

Students of city history may remember that the CTU foundation was the vehicle for selling Fewkes Tower, a high-rise in Old Town originally intended to house retired teachers. The union sold the tower for $50 million, with the proceeds flowing into the Foundation. Leadership then spent that money in part on a new headquarters in the West Loop. That new headquarters is owned by the foundation and charges rent to the union.

Gates doubles as the president of the foundation, and CTU Vice President Jackson Potter doubles as vice president.

Spin zone

The Department of Labor last week sent a letter to CTU asking for a meeting to “obtain detailed information about the union and its financial records, bookkeeping practices, and internal controls,” according to reporting from The Intercept.

These discrepancies certainly warrant that.

But union leadership and their political allies have attempted to mask the audits controversy by attacking the messengers, and implying the demands for transparency are political in nature.

On Jan. 15, U.S. Rep. Delia Ramirez, D-Illinois, sent a letter to the House Education and Workforce Committee complaining the committee had requested the audits “based on citations exclusively from the Illinois Policy Institute.” Ramirez’s campaign committee has received more than $289,000 from the CTU.

And just prior to releasing the audits, the union planted two stories claiming the demands for transparency were concocted by “MAGA Republicans.”

Observers may note Liberty Justice Center, the firm representing CTU members in the audits case, is also suing the Trump administration. Specifically, Liberty Justice Center argued the marquee case challenging the legality of Trump’s sweeping global tariffs before the Supreme Court, with a ruling expected as soon as Jan. 20.

In the news

The Washington Post published my piece on how you can’t start a Chicago-style hot dog cart in Chicago, featuring artwork by Adrián Astorgano.

Last week’s edition of The Last Ward was cited by Nellie Bowles at The Free Press in her popular TGIF newsletter.

And I joined the Mincing Rascals podcast on WGN Radio.

My “green light” recommendation: No Other Choice (2025), now playing at the Music Box Theatre.

Chicago Board of Education President Sean Harden called a special meeting over the Christmas holiday. He had one objective: Quietly pass a $25 million property tax hike.

One might understand why Harden wanted to keep it under wraps.

Weeks earlier, Chicago homeowners saw the largest residential property tax hike in at least 30 years. And the man who appointed Harden to his post, Mayor Brandon Johnson, just spent months talking about how he was refusing to hike property taxes as part of the city budget.

Best not to mix messages.

But Harden’s plan hit a snag. Fox 32 Chicago political reporter Paris Schutz published news of the meeting before the school board posted a public notice of its own.

And now Harden—with Johnson’s imprimatur—is spending taxpayer money on a law firm to conduct an investigation into how news of the meeting leaked to a journalist.1

The headline is Onion-esque: Mayor uses property taxes to investigate how residents learned of higher property taxes.

But there’s a deeper lesson here.

The real problem

Here is one maxim of Chicago’s political culture: The more dramatic the story, the less likely residents will grasp its most important lessons. Call it Gift Room Syndrome.2 And it certainly applies here.

The big scandal isn’t the board voting to hike property taxes by $25 million, though that is worth noting. (You can find the roll call below.)

MEMBERS VOTING NO (5): Carlos Rivas; Ellen Rosenfeld; Angel Gutierrez; Che “Rhymefest” Smith; Therese Boyle. MEMBERS VOTING YES (15): Jennifer Custer; Jessica Biggs; Yesenia Lopez; Ed Bannon; Anusha Thotakura; Ebony DeBerry; Cydney Wallace; Karen Zaccor; Olga Bautista; Emma Lozano; Michilla Blaise; Norma Rios-Sierra; Angel Velez; Jitu Brown; Debby Pope. Don’t know your board member? Click here.

And while it is absurd, of course, the big scandal isn’t even the investigation into how taxpayers learned about the meeting.

The biggest scandal here is that the school board is subverting democracy.

Specifically, Chicagoans should be seeing a referendum vote on an extra $550 million increase in property tax collections that will flow to Chicago Public Schools this year, above what’s allowed under the state’s property tax cap.

But Chicagoans will not get that vote.

How CPS is ignoring voters

Illinois has a property-tax cap in state law. That cap limits how much local school boards can hike property taxes in a given year. Go above the cap, and the board must ask voters for permission via referendum on the ballot.

Every year, the Chicago school board votes to hike property taxes up to the maximum allowed without triggering a referendum. And this time was no different, as CPS Chief Financial Officer Wally Stock explained at the Dec. 29 board meeting.

But if those board votes were the only source of CPS property tax growth, Chicagoans should have expected property taxes for schools to increase by around 50% from 2006-2023.

Instead, CPS property taxes grew by more than 100% over that time.

And Chicagoans never got to vote on it.

The main reason for growth in property taxes exceeding the state cap is the TIF loophole. In short, the city squirrels away money into Tax Increment Financing (TIF) districts, but then sweeps those TIF funds into CPS and other local governments. And the TIF sweeps don’t count toward the property tax cap. This is why TIFs are best understood not as an economic development tool, but as Chicago’s secret property tax hikes.

Because of that loophole, $550 million in extra property tax revenue above the cap will flow into CPS this year—without a vote of the people.

That’s the real scandal.

Voting on higher taxes, debt

Getting voter sign-off on new borrowing or property tax hikes beyond a certain limit is a common practice in big cities across the country.

But not in Chicago.

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As the Wall Street Journal editorial board recently highlighted:

Nearly every other U.S. big city requires voter approval for increasing general obligation debt. In Los Angeles, Houston, Phoenix, San Antonio, San Diego and others, voters are required to approve general obligation bonds, according to the Chicago Policy Center. New York and Chicago don’t require voter approval.

The reason for requiring voter approval is simple: accountability. It forces public officials to show their work.3

In the news

Last week’s edition of The Last Ward on why you can’t start a Chicago-style hot dog cart in Chicago got a lot of attention. In short: There is strong, bipartisan support for #hotdogabundance. Keep an eye out for another piece on this topic in a major national outlet this week.

I joined The Mincing Rascals podcast on WGN last week to discuss the ICE shooting in Minneapolis, Nicolás Maduro’s capture, and the Chicago mayoral race. You can listen wherever you get your podcasts (including, for the first time, YouTube).

My “green light” recommendation: the Chicago Printmakers Collaborative in Lincoln Square, which is home to this incredible sign.

In Los Angeles, bacon-wrapped hot dogs are a street food staple.

New York City’s “hot dog king” Dan Rossi runs a legendary stand outside the Met.

And an IRS attorney on furlough went viral last fall for starting his dream hot dog cart in Washington D.C.

But in the home of Chicago-style hot dogs, there is not a single food-cart vendor licensed to sell hot dogs on a city sidewalk, according to a Chicago Policy Center review of city data.1

No matter one’s culinary talent or work ethic, city regulations make hot dogs—and other street-food staples—effectively illegal to sell from a cart.

With tamale vendors facing unprecedented crackdowns from federal agents, a weak city job market, and candidates for mayor and City Council preparing for municipal election season, is it finally time for the city to stop criminalizing street food?

Food fight

For decades, Chicago was one of only two cities in the top 25 by population that did not allow food-cart street vending at all.2

Risk-averse city officials and lobbyists for brick-and-mortar restaurants worked together to keep it that way.

But in 2015, I was fortunate to work on what remains the largest-ever survey of Chicago food-cart vendors, and met inspiring women like Claudia, Cecilia, and Joaquina who woke before dawn each day to prepare tamales and sell them on the street to support their families.

Survey data from nearly 200 of the estimated 1,500 food-cart street vendors across Chicago found an industry generating an estimated $35.2 million in annual sales, $16.7 million in annual income, 2,100 jobs, and 50,000 meals a day—supporting 5,000 dependents.

But it was all underground.

Vendors risked daily harassment from criminals and law enforcement alike.

So I was proud to stand with those women and their families at City Hall on Sept. 24, 2015, when City Council passed an ordinance creating the first modern license for food-cart vendors in Chicago.

A year later, I profiled the recipients of the first licenses for tamale carts: Abraham and Maria Celio, owners of Yolis Tamales in Back of the Yards.

“We feel a lot of pride, a lot of happiness,” Maria said. “And we feel more secure and confident in selling our food. We aren’t working with the fear of being fined.”

But nearly a decade later, the Celios are among just three licensed tamale cart vendors in a city of 2.7 million people. In fact, their family is one of only 12 licensed food-cart vendors of any kind in Chicago.

“I feel happy for my father, who doesn’t have to worry about police anymore,” Abraham said.

“But at the same time, I feel sad for people who still struggle and have not been able to get the license.”

So what went wrong?

Unreasonable rules

The 2015 ordinance created a new license for food-cart vendors called the Mobile Prepared Food Vendor license.

But in its design, the city shut out virtually all food-cart vendors that Chicagoans see on the street today.

Critically, the license does not allow for food handling of any kind on a cart.

A key provision notes that “food may not be prepared on or in” a food cart. And the city interprets “preparing” food to mean an action as small as placing a hot dog on a bun.

That’s one reason Chicagoans don’t see Chicago-style hot dog carts.

Even dispensing coffee from an urn counts as “preparing” and thus cannot happen on a cart. This prevents scores of champurrado vendors across the city from getting a license, for example.

City rules also don’t allow for carts with a propane tank, which bans vendors from using slick new carts like The Tamalero, which is legal in Los Angeles. This is another hurdle for tamale vendors and hot dog vendors alike.

Abraham and Maria Celio were able to pour thousands of dollars into designing and fabricating their custom tamale carts with direct input from city regulators—and critically, can prepare their tamales in the licensed commercial kitchen in their own brick-and-mortar restaurant—but they are the exception.3

Chicago’s tamale vendors are daunted by the paperwork, the process, and the overly restrictive rules.

So they remain unlicensed.

New York City expanding

New York City, already home to 7,000 licensed mobile food vendors, will add an additional 2,200 mobile food vendor licenses each year for the next five years under a bill passed by City Council in December.

Newly elected Mayor Zohran Mamdani is expected to sign it.

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Indeed, Mamdani built early momentum in his historic campaign by championing the city’s street vendors, noting red tape was driving “halal-flation.”

Regardless of their feelings on other elements on Mamdani’s agenda, enterprising candidates for Chicago mayor and City Council in 2027 would be wise to take on the same underdog fight on behalf of Chicago’s street vendors.

Unseen costs

In 1963, a 23-year-old returning from the Marines purchased a 6’ by 12’ trailer for $1,100 to start The Dog House in Villa Park.

The trailer had no bathroom and relied on running 250 feet of garden hose from a nearby building for running water.

That man was Dick Portillo.

In 1893, Austrian-Hungarian immigrants Emil Reichel and Sam Ladany introduced their all-beef sausages at the World’s Fair. The success of their small hot dog stand at the Austrian Village exhibit led to their first storefront a year later.

That business would go on to become Vienna Beef—the foundation of the Chicago-syle hot dog.

These stories show how today’s food-cart regulations are killing tomorrow’s titans of Chicago’s culinary community.

City leaders ought to change them.

Chicago City Council made history this week by passing an “alternative” budget—something it arguably has never done before.

On its face, that’s a good thing. The Council showed rare independence by rejecting Mayor Brandon Johnson’s proposed head tax and forcing changes to a record $16.6 billion spending plan.1

But independence alone does not equal responsibility.

The reason this budget still fails is the same reason Chicago keeps repeating the same fiscal mistakes: City Council lacks the institutional capacity to govern, the mayor retains nearly all the power needed to shape outcomes, and voters have no formal role in approving major financial decisions.

It’s why the process seemed adversarial, but ultimately produced a budget that was, in substance, almost identical to the one it was supposed to replace.

That contradiction defines Chicago budgeting—and explains why this moment, while encouraging, is still deeply insufficient.

Budget games

Chicago’s budget process echoes Drew Carey’s description of Whose Line Is It Anyway?

It’s a show where everything is made up and the points don’t matter.

The mayor controls an army of analysts, legal staff, and oftentimes, access to basic financial information. City Council, by contrast, relies on the City Council Office of Financial Analysis—an office of four people—to evaluate a $16.6 billion budget.

That imbalance explains why, even this year, the Council’s “alternate” budget remains roughly 98% identical to the mayor’s original proposal. While the new budget is different in that it makes a larger pension payment and axes the head tax, there are some concerning similarities with Johnson’s.

Here are three lowlights they share in common:

1. A record one-time TIF sweep of over $1 billion, which gives Chicago Public Schools a property tax windfall of $550 million. This functions as a property tax hike that avoids the voter participation required under the state’s tax-cap framework.

2. Excessive, back-loaded borrowing in part to fund operating expenses, including Chicago Fire Department back pay from a new contract the city knew it could not fund without debt.

3. No skin in the game from government employees. No pay cuts. No pay freezes. No furlough days. And no reforms to pay more for extremely generous healthcare benefits, as recommended in a recent EY report on efficiencies.2

These three factors combined could trigger another credit downgrade for Chicago.

Ald. Anthony Beale put it in a nutshell with his speech on the Council floor Saturday, before voting in favor of the alternative budget. While acknowledging that what the Council accomplished with extremely limited resources was impressive, which is true, he also showed how the mayor’s office still holds all the cards, forcing poor decision-making:

Last year, we sat in this very seat and we said over and over again to the budget director, ‘Is the money for the fire contract in the budget? Oh yes, it’s in the budget. We’ve set that money aside. That money’s in the budget.’ Now we found out that the money was spent and now we’re borrowing to pay for the fire contract…Did they come to us and say, ‘Aldermen we have a financial problem. We need to spend the fire money that we set aside’? No they didn’t. They spent it, and then came back and lied to us on why they had to spend it. So who are we going to put faith in?

There was a potential silver lining to this budget fight as part of the “management ordinance,” which is one element of the overall budget package. Council members originally considered adding provisions to give themselves more permanent infrastructure for fiscal oversight and analysis, akin to an independent budget office. There was also a provision requiring automatic Council hearings should the Chicago Police Department exceed its overtime budget (a perennial problem). But those items were unfortuately dropped from the management ordinance.

It is a good thing that Chicago does not have a rubber-stamp City Council right now.

But without the proper resources and safeguards, that independent Council will make poor decisions, or simply return to being a rubber stamp under a new administration.

On the other hand, if officials can learn from this experience, it could prove to be truly transformational.

Fait accompli

When given the choice of angering labor or borrowing money without going to voters, Chicago politicians will borrow money without going to voters.

That’s why Chicago has the worst debt problem of any major city in the country, which JPMorgan market strategist Michael Cembalest discussed in a popular recent episode of the Illinois Policy Podcast.

The three lowlights listed above just wouldn’t be viable in many other big cities.

For one, of the 15 largest cities in the country, 13 require some form of voter approval before issuing general obligation bonds. Only New York and Chicago do not. And New York City enjoys a suite of other fiscal safety measures Chicago lacks, including an independently elected comptroller with substantial power, GAAP accounting rules, and an Independent Budget Office.

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In other cities, these basic fiscal accountability measures live in a city charter that can’t be changed with a simple majority vote. But Chicago is the only major city that has no charter. Illinois state lawmakers should give Chicago’s leaders and voters the power to create one.

Given the concerning case study presented by the budget process this year, I predict an unprecedented legislative focus on city charter reform in 2026.

In the news

The Washington Post cited The Last Ward in their editorial (“Chicago has lost its mind”) last week:

As Austin Berg of the Illinois Policy Institute said, when the firefighters ran out of cash, the city got a taste of what insolvency looks like. Unless politicians get serious, actually cut spending and start enacting sane, pro-growth policies, Chicago will get more than a taste of that bitter pill.

Illinois State Rep. Maurice West, D-Rockford, referenced changing municipal election timing in his remarks at the City Club last week. Chicago is the only big city in the country to hold municipal elections in February. This is an insidious form of voter suppression.3

I joined former Chicago Tribune columnist John Kass and Jeff Carlin on their podcast The Chicago Way to discuss the city budget, the upcoming Chicago mayoral race, and last week’s edition of The Last Ward on the truth about TIFs.

And I joined John Williams, Eric Zorn and Marj Halperin on the Mincing Rascals podcast to discuss Gregory Bovino’s brief return to Chicago, the city budget, and Gov. JB Pritzker signing the Medical Aid in Dying bill. My “green light” recommendation: Charlie Dark on Theo Parrish.

Chicago has just over two weeks left to pass a city budget. The clock is ticking.

Much of the budget drama has centered around Mayor Brandon Johnson’s demand for a controversial “head tax,” which would bring in an estimated $82 million.1

But far less attention has been paid to a move with a far greater impact on the budget: the mayor’s proposed $1 billion sweep of Tax Increment Financing districts, or TIFs.

It is impossible to understand the current budget battle—and the record-breaking property tax increases that just hit Chicago homeowners—without first understanding TIFs.

In this week’s edition of The Last Ward, we dive into a critically important part of the budget process that most voters don’t understand. And how political leaders are taking advantage of that ignorance to pass back-door property tax hikes, costing homeowners thousands of dollars a year.

What are TIFs?

In theory, TIFs are supposed to be economic development tools.

In practice, TIFs have become a core feature of Chicago’s operating budget, one of many poorly governed elements in the city’s budgeting process.

Here’s how TIFs are supposed to work:

1. The mayor signs an ordinance, passed by City Council, creating a TIF district in a “blighted” area of the city.

2. Within a TIF district, property values grow, which means higher property tax collections.

3. Those incrementally higher property tax collections are skimmed off into a TIF fund every year. Meanwhile, the frozen “base” of property tax collections in the district continue flowing to the city, the schools, the parks and other local governments. Each TIF district lasts 23 years.2

4. The city uses the TIF funds for projects inside the TIF district, or nearby, to eliminate blight and spur redevelopment.

But here’s how TIFs actually work in Chicago:

1. The city is blanketed with 108 TIF districts, including downtown areas like LaSalle Street that could hardly be described as “blighted.”

2. TIFs captured a record 42% of the city’s property tax revenue in 2023. This is an extraordinary share unmatched by any other major U.S. city.

3. Some TIF dollars fund economic development. The Chicago Riverwalk is a prominent example of a worthy, TIF-funded project. The Wintrust Arena is a prominent example of a dubious one.

4. Increasingly, TIF functions as a shadow budget for the city and Chicago Public Schools. Instead of being spent on redevelopment, funds are routinely swept as part of the city’s budgeting process and used to plug operating deficits. As we’ll see, this practice allows CPS to boost its property tax collections without seeking approval from voters.

To get a sense of Chicago’s unprecedented reliance on TIFs to plug budget holes, here’s the declared TIF surplus each year since 2017, and the share of that surplus flowing into the city’s operating budget.

That brings us to the current budget fight, which is expected to come to a head during a string of City Council meetings this week.

The TIF shell game

Mayor Brandon Johnson is proposing a record $1.01 billion TIF sweep to help fund the city’s operating budget. But it’s not just the city. Per state law, any TIF “surplus” must be distributed proportionally to local governments.

That’s where the shell game begins. Here’s how it works:

• The entity getting the largest chunk of Johnson’s proposed TIF sweep by far is Chicago Public Schools, which would receive $550 million.

• But the current CPS budget only relies on $379 million from TIFs. The alternate budget supported by a majority of City Council members proposes a smaller TIF sweep—enough to generate that $379 million for CPS.

• Johnson is pushing the higher, $1 billion sweep so CPS can then turn around and make a $175 million pension payment back to the city. This is exemplary of the shell games at play with TIF, which ultimately moves money in circles, obscuring who is taxing whom—and why.

It’s easy to see how TIFs fly in the face of their stated purpose. And how they allow for shell games with budgeting.

But the more important (and perhaps least understood) element of TIFs is how they trigger higher property tax bills.

TIFs cause property tax hikes without a vote

Typical Chicago homeowners saw their property tax bills jump 17% this year, according to the Cook County Treasurer’s Office. That’s the largest increase in 30 years.

Chicago Tribune reporter A.D. Quig wrote a great story about those growing property tax bills, and readers took note of the graphic below, showing the extent to which the city’s growing property tax burden is the result of Chicago Public Schools. The CPS property tax levy grew to $3.99 billion in 2024 from $2.56 billion in 2014.

A fantastic new report from the Civic Federation and the Mansueto Institute for Urban Innovation at the University of Chicago shows how CPS is running an end-around to grow property tax levies far beyond what state law is supposed to allow—with TIFs playing a key role.

Here are the toplines:

• CPS is subject to a statewide property tax cap called the Property Tax Extension Limitation Law, or PTELL, which is supposed to limit annual growth in its property tax levy to the lesser of inflation or 5%.

• If CPS wants to hike property taxes beyond that limit, the district is required to ask voters for permission via referendum.

• From 2006-2023, the CPS property tax levy should have grown by around 50% under PTELL. Instead, CPS grew its property tax levy by more than 100% over that time period. But Chicagoans never got to vote.

• Why? Due to a loophole in PTELL, the hundreds of millions of dollars in property tax revenue sent to CPS via TIF surpluses every year don’t count toward the property tax cap. CPS also levies a special property tax charge to fund pensions that doesn’t count toward PTELL.

In short, CPS maxes out its PTELL-capped levy every year, and then collects TIF surplus money and other “uncapped” funds on top of that. The result: Runaway property tax increases with voters having no say.

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The blue line below shows the growth in the CPS property tax levy if the district had fully obeyed the property tax cap. The green line shows what actually happened.

If CPS had not exploited the loopholes in PTELL, the typical homeowner in Chicago would have saved more than $300 on their property tax bill in 2023 alone, according to the report.

And if every local government into which Chicagoans pay property taxes had been subject to PTELL without loopholes from 2007-2023, the numbers are even more stunning. Here’s a simple breakdown.

Chicago taxpayers would have saved almost $4 billion on their property taxes if local governments were actually restrained by the property tax cap from 2007-2023: $2 billion in savings for residential properties and $2 billion for commercial properties. In 2023 alone, Chicagoans would have saved $550 million on their property taxes.

Fix the loopholes and sunset TIFs

If political leaders can abuse TIFs as an end-around for sensible limits on property tax growth, that means both TIFs and the state’s property tax caps are broken.

To fix this, state lawmakers should close the TIF loophole in PTELL. And City Council should allow current TIFs to sunset.3 To spur development in truly blighted areas, the city could use simple, shorter-term property tax abatements instead.

Stop the shell games, and let voters decide whether to hike property taxes beyond inflation.

In the news

I joined Jon Hansen and Brandon Pope on WGN Radio for the Mincing Rascals podcast to talk about the head tax, sidewalk delivery robots in Chicago, former House Speaker Michael Madigan’s prison sentence and more. Listen here.4

Earlier this year, the Chicago Policy Center joined the Better Government Association and the Civic Federation to screen Drop Dead City, a vital documentary on New York City’s brush with bankruptcy in 1975. The film is now available to stream on Amazon.

My “green light” recommendation: I cannot recommend more highly “Songs of Good Cheer,” the annual holiday caroling tradition helmed by Mary Schmich and Eric Zorn, which is staged at the Old Town School of Folk Music and entering its 27th year. Tickets to the final show of the season this afternoon are sold out. Set a calendar reminder for 2026 if you missed it.

Yodeling to “The Friendly Beasts,” a Christmas song that originated in 12th century France.

As Chicagoans gather for the holidays, here’s a party trick to make the whole room groan like the hull of a wooden ship.

All you have to do is say two words.

“Parking meters.”

On Dec. 4, 2008, in the span of about 72 hours, Chicago handed 36,000 parking meters to private investors for 75 years in exchange for $1.15 billion in cash up front. Seventeen years later, the meters have generated $2 billion for the investors, with 58 years still left on the lease.

Parking rates spiked. Neighborhood business districts lost what had once been a flexible tool of local policy. And City Hall lost control of its own curbs. Adding insult to injury, a significant share of the equity in the Morgan Stanley-led deal traces back to the sovereign wealth fund of the United Arab Emirates—meaning a portion of every dollar Chicagoans feed into a meter ultimately flows to a foreign government.

The parking meter deal is the most infamous political tale in modern Chicago history. It dominates how normal people think about City Hall. It is maybe the one thing Chicagoans of all political stripes agree on: they hate it.

Yet, despite all the attention, Chicago learned the wrong lessons from the parking meter deal. And because of that, the city is still repeating the same mistakes.

What actually happened that week

Here’s the basic timeline of the deal:

• Dec. 2–3, 2008: Chicago Mayor Richard M. Daley’s team unveils a proposed 75-year lease of the city’s metered parking system to Chicago Parking Meters, LLC, for $1.15 billion.

• Dec. 4, 2008: The City Council votes 40–5 to approve the deal after only a few days with a 500-plus-page agreement.

• Within two years: The city blows through almost the entire windfall to plug budget holes, instead of locking it away in a dedicated fund.

• June 2, 2009: Inspector General David Hoffman’s office finds the city was paid, conservatively, $974 million less for the deal than it would have received from 75 years of parking-meter revenue had it retained the system under the same terms that the city agreed to in the lease.

Here’s the whole saga in one sentence: Chicago sold a long-term, flexible revenue source to solve a short-term cash problem, at a discount, under rushed conditions, for an absurdly long term.1

Chicagoans threw up their arms in disgust.

But disgust at what, exactly?

The wrong lessons

1. “The problem was corruption.”

For a lot of Chicagoans, the parking meter deal is proof that Chicago is uniquely corrupt—that this could only happen here. And it’s true: “corruption” played a role.2 Private interests clearly took advantage of an open net. But explaining the deal only with “Chicago is corrupt” misses the more important point: Our system is structurally unsound in a way that gives ordinary corrupting influences extraordinary power.

Every big city has lobbyists, bankers, law firms, and sovereign wealth funds eager to gobble up public assets. What made Chicago such an easy mark wasn’t that our people are uniquely evil. It’s that our operating system is unusually flimsy. And if you focus only on crooks, the solution is then simply to elect nicer people, and hope for the best.

2. “The problem was Daley.”

Daley deserves a huge share of the blame. But if this becomes just a Daley morality play, the city tells itself a comforting story: The machine did this. And since the Daley machine is gone, we’re safe. The truth is uglier: Daley used the system as designed. One office, the mayor, was negotiating the deal. One office, the mayor, was directly presiding over the legislators voting on the deal. One office, the mayor, held the keys to the information and staff time necessary for City Council to vet the deal. That system still exists today.

3. “The problem was privatization.”

A third lesson many people took is that privatization itself is always a scam. But that’s also too easy. There are services that can be sensibly contracted out. There’s a real debate to be had about fully privatizing Midway Airport, for example. But the problem is doing large-scale privatization inside a broken structure. Chicago is like a factory that keeps bolting on experimental machinery without having working safety systems. City government should not be running high-risk maneuvers with our most precious public assets with no basic guardrails in place.

The right lessons

The clearest way to see what actually went wrong with Chicago’s system is to ask: What if another big city tried this?

The most helpful example in New York City, where long-term use of public assets is governed by the city’s charter. Here’s how a Chicago-style parking meter deal would have gone down:

• A citywide on-street parking concession would trigger review and approval by the Franchise and Concession Review Committee, or FCRC, which includes the mayor, the budget director, the city’s top lawyer, the independently elected comptroller, a mayoral appointee, and a representative of the borough presidents.

• Under New York’s charter and implementing rules, these deals are time-limited. Franchises generally can’t exceed 25 years under the charter, and the FCRC’s rules cap concessions at 20 years (including extensions) unless the committee unanimously finds “extraordinary circumstances” to go longer.

• To pass Chicago’s 75-year lease, New York would have to amend its charter to relax those limits. And under §38 of the New York City Charter, any local law that changes provisions relating to public utility franchises or removes charter restrictions on the sale or lease of city property must be submitted to the voters for approval.

In short, a Chicago-style parking meter deal would be theoretically possible in New York City. But it would be a political moonshot, because the city charter forces these deals into daylight, with more actors involved and stricter limits. And in some cases, that means getting approval directly from voters.

But Chicago does not have a city charter. The process for deals like this is governed by which political figure can count up to 26 votes in the council. That’s it.

Chicago didn’t fix the problem

After the outrage, Chicago “did something” by passing the 2015 Privatization Transparency, Accountability, and Performance Ordinance.

Drafted explicitly in response to the parking meter debacle, it requires independent financial analysis from outside advisors, public posting of deal terms, and minimum waiting periods between when a deal is introduced and when the City Council can vote.

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It’s better than nothing. But it has a fatal flaw: it is an ordinary ordinance that can be erased or weakened with a simple majority vote. Chicago created a bit more process. But the city did not create real constraints.

Proof we haven’t learned

If the parking meter mess had truly changed how Chicago behaves, the city would treat it as a turning point. Instead, leaders found new ways to sell off the future.

Earlier this year, the City Council approved an $830 million general obligation bond package backed by Mayor Brandon Johnson. The headline was infrastructure spending. The real story was the structure of the debt:

• The total repayment cost is projected to be roughly $2 billion, to borrow $830 million

• For the first two years, the city makes no payments at all. Nothing in FY2025 or FY2026.

• The city makes interest-only payments through 2043—meaning taxpayers make no dent in the principal for 18 years, long after the current administration and most current aldermen have left office.

In most other big cities, this borrowing plan would have been subject to independent analysis from a controller, a robust City Council, and ultimately voters.

But Chicago has none of these controls, much less a charter that can protect them from political whims.

What Chicagoans should actually hate

Jeff Tweedy once remarked that his favorite lyric he’s ever written was “Hate will save the dolphins.”

A sad reality of politics is that hatred is often more powerful than love. It unifies people who might agree on little else.

Chicagoans are right to hate the parking meter deal. The trick is to hate it for the right reasons. And to harness that energy to build a governance structure where a 75-year heist in 72 hours cannot happen again.