Chicago City Council last week finalized six questions that will appear before Chicago voters.

But do those questions actually matter?

Let’s take a look.

All six measures are non-binding, meaning they are essentially poll questions.

Media coverage on these questions highlighted how Mayor Brandon Johnson’s preferred non-binding referendum—asking voters to weigh in on whether the state should pursue a “millionaires tax”—failed to make it to the ballot.1 And in response, how Johnson berated City Council members.

Compare that political food fight to what New York City voters will decide on their ballots this November.

The day after Johnson’s push officially failed, New York City Mayor Zohran Mamdani’s charter revision commission (dubbed the Commission on Government Efficiency, or COGE) voted to put five binding propositions before voters that make changes to the city’s governance structure.

If approved, those structural changes will lead to faster approval for outdoor dining permits, streamlined city contracting, accelerated bike lane construction, a simplified building permit regime, and clear goals for the city’s rainy day fund.

In short: voters’ choices will actually matter.

Chicago discourages democracy

Lacking real options on the ballot is a symptom of a larger problem in Chicago. No other big city does more to discourage democratic participation in local government.

Here are five examples:

1. The rule of three: Non-binding questions can be useful. But in Chicago, they crowd out valuable ballot space. That’s because state law sets a “rule of three” in city elections, meaning only three referenda can appear at any one time.2 Lawmakers can use the rule of three to box out citizen-initiated referenda. So it’s no surprise Chicago voters haven’t decided a single issue on the ballot via citizen initiative in modern history.

2. Severely gerrymandered wards: Chicago politicians can pick their voters. Chicago City Council members, in concert with the mayor’s office, draw their own districts to reward friends and punish enemies.

3. February elections: Chicago is the only big city in the country that holds its municipal elections in February of an odd year. This timing suppresses voter turnout by 40%.

4. No city charter: Chicago is the only big city in the country without a charter. That means there is no mechanism nor civic culture for charter revision. Across the country, big-city charter revisions routinely offer voters the opportunity to decide serious governance matters.

5. Poor selection of elected offices: Chicagoans elect one citywide office that truly matters: the mayor. The other two citywide offices (clerk and treasurer) have very little authority. Unlike other big cities, Chicagoans do not elect an independent city attorney or chief financial officer.

And that final point isn’t just a city problem.

Chicagoans are now seeing the consequences of a similar dynamic at the county level on their property tax bills.

Too many cooks in Cook County

I joined WGN’s Ben Bradley this week for his story on Cook County’s failed property tax modernization effort.

The county has spent more than $63 million over the last decade attempting to update its property tax system. But that system is still broken. And delayed property tax collections are costing local governments tens of millions of dollars in short-term borrowing costs.

A new Cook County inspector general report found mismanagement of the project was a “perfect storm,” in large part due to the politicization of what should be purely bureaucratic offices.

From Bradley’s story:

The inspector general concluded that the transition to the new technology was imperiled by the conflicting agendas of elected officials and by a lack of cooperation from some officeholders…

The Chicago Policy Center‘s Austin Berg says the tech trouble is the perfect example of having too many cooks – or in this case, politicians – in the kitchen.

“Cook County needs an assessor. We need a board president. We need a clerk, but those don’t necessarily need to be elected offices that are completely separate and independent,” Berg said. “We saw here the result of that, just being a complete mess in trying to do something the county really needs.”

In the news

Quigley backs charter: U.S. Rep. Mike Quigley, D-Chicago, is running for mayor. He recently published a lengthy, detailed essay on why Chicago needs a city charter: “I Want to Be Mayor and I Want Mayors to Have Less Power.” Highly recommended.

The emptiest big-city school in the nation: I joined Good Day Chicago for a deep dive into last week’s edition of the Last Ward, which found Frederick Douglass Academy High School is the emptiest big-city school in the nation.

On the numbers:

The math is not math-ing. More full-time employees than students [and] almost double the number of classrooms as students at Frederick Douglass Academy. These statistics to the common person in Chicago are just shocking. The reason is that Chicago Public Schools has no framework, that is public, for what happens: what are the minimum standards for enrollment and performance at a school, and what are the high-bar standards that would trigger replication of a school? We lack a framework for both. In absence of that framework all we have in Chicago is a moratorium on school consolidation. So we don’t have a real plan. We simply have a big sign that says “no.”

On how empty schools hurt the district’s ability to get more resources:

The school district is in a position where it is increasingly needing to go to the state for additional resources. Imagine you’re a state lawmaker and a lobbyist comes to you saying we need more money for Chicago Public Schools. How can you feel good about that decision when you have a school spending $93,000 per student per year and it’s only 3% utilized. The emptiest big-city school in the country. It hurts the district’s ability to advocate for itself at the state level.

On the mayor’s preferred solution:

Mayor Brandon Johnson and the Chicago Teachers Union, when faced with questions about under-enrolled schools like this, they point to a model called the Sustainable Community Schools model, which is more about providing additional staff and additional wraparound services at schools. The problem with that model is at the eight high schools that have used [it] since 2018, we see proficiency is down, enrollment is down, absenteeism is up, and spending is up.

On our CPS Excellence Agenda:

We’re calling for a Blue Ribbon Commission [on facilities planning] from the newly elected school board in November that can actually build a framework for how we properly use our facilities to better serve students.

City housing debate: Housing reform is a key component of the Chicago Abundance Agenda. Veteran City Hall reporter Fran Spielman convened a fantastic housing debate last week between Zoning Committee Chair Ald. Gil Villegas (36th Ward) and Chicago Housing Commissioner Lissette Castañeda.

Frederick Douglass learned to read in secret.

He understood from a young age that literacy was, in his words, “the pathway from slavery to freedom.”

But at Frederick Douglass Academy High School in Chicago, the school is so under-enrolled that Illinois cannot publicly report how many of its students read proficiently. There simply aren’t enough tested students to publish the results without risking their anonymity.1

Douglass Academy has 47 classrooms built to serve 1,008 kids. But only 27 students are enrolled there.

At 3% utilization, it is the emptiest big-city school in the country, according to Chicago Policy Center research.2

Meanwhile, CPS personnel records show Douglass currently employs 28 full-time staff members.3

In a district that once served nearly 600,000 students and now serves 312,000, and where one-third of school buildings sit at least half empty, Douglass illustrates the consequences of poor facilities planning: fewer opportunities for students and higher costs for taxpayers.

Empty schools harm students

If a student in Illinois misses more than 10% of school days in a year, they are considered chronically absent. At Douglass, 100% of seniors are chronically absent.

And while the state couldn’t report test scores for the most recent school year, not a single 11th-grade student at Douglass could read or perform math at grade level in the 2023-2024 school year.

This isn’t due to underfunding. In the 2023-24 school year, Douglass spent $93,000 per student.

The real issue is simple: Research has long shown that very small high schools struggle to provide the breadth of academic courses and extracurricular opportunities available at larger schools.

An analysis published by ProPublica and Chalkbeat found the level of under-enrollment at CPS schools like Douglass deprives students of clubs, sports, and other extracurriculars critical to a healthy learning environment.

So what should district leaders do about it?

Addressing empty schools

Chicago Mayor Brandon Johnson and the Chicago Teachers Union have argued the solution to Douglass’ problems is the Sustainable Community Schools model.

But the results are in at eight CPS high schools that have used this model since 2018: proficiency and enrollment have continued to decline, while spending and absenteeism are up.

Today, 47 Chicago schools are operating at one-third capacity. That’s double the number the district faced in 2013 when it closed 50 schools.4

But Chicago is hardly alone.

Declining enrollment in big-city districts across the country has forced leaders to rethink their facilities planning to better meet students’ needs:

• The Philadelphia school board approved the closure of 17 schools after experiencing a 12% drop in enrollment over the last decade, and launched a Facilities Data Dashboard to help “develop recommendations on which buildings to maintain, modernize, co-locate, repurpose, or close.”

• San Antonio schools commissioned a study on building capacity in 2023 and have since voted to close 15 campuses, repurposing four.

• New York City closed two schools and merged 16 schools in recent years, while opening 28 new schools.

• In Columbus, the Community Facilities Task Force made recommendations to the school board, leading to board approval on five school closures or consolidations starting in the 2026-27 school year.

It’s past time for Chicago to start planning smarter.

A better path forward

The Chicago Policy Center’s CPS Excellence Agenda provides a Day 1 work plan for Chicago school board candidates hoping to win their elections this November.

One key recommendation: Convening a Blue Ribbon Commission for CPS facilities planning, which should:

• Assess the current facility footprint.

• Establish an ongoing framework for optimizing school facilities for student success, including core principles of school utilization, neighborhood coverage, and model school staffing.

• Set a consistent minimum standard for schools in terms of enrollment and performance, as well as a consistent “high bar” standard that triggers school-model replication.

• Compare CPS’ capital financing ability to other large districts.

The name Frederick Douglass should stand for the expansion of educational opportunity, not the preservation of an empty building.

Chicago students deserve the opportunities his legacy demands.

In the news

I joined the Mincing Rascals on WGN this week to discuss Chicago policing, the Illinois secessionists, and more (Apple Podcasts, Spotify).

Chicago Public Schools has produced some of the world’s brightest stars.

But candidates for the November school board elections—the first fully elected school board in Chicago history—face a raging storm within the nation's fourth-largest school district.

On Nov. 3, Chicagoans will elect 20 school board members and a citywide board president. Consider:

• CPS has a junk credit rating, and is the largest junk-bond issuer of any municipal government in the nation.

• Math and reading outcomes for CPS fourth graders declined faster than any peer district from 2017-2024.

• When asked to grade Chicago schools on how well they prepare students, just 17% of Chicagoans give the district an A or a B.1

• CPS serves 316,000 students today, down from a peak of nearly 600,000.2

All Chicago families deserve to enjoy the highest-performing big-city school district in the nation. But that requires a school board capable of governing with conviction and confidence on Day 1.

Thankfully, CPS board members don’t have to invent a turnaround model from scratch. Drawing lessons from school districts across the country, the Chicago Policy Center compiled the CPS Excellence Agenda, built on three pillars:

1. Academic excellence

2. Financial excellence

3. Board excellence

Candidates should begin with the question that matters most: Are students learning?

Academic excellence at CPS

Chicago Mayor Brandon Johnson said he would grade school performance on spending, not outcomes. But 78% of Chicagoans believe the main goal of public schools should be preparing students to be good citizens, to go to college, or to get a good job. Student outcomes are the defining measure of a thriving school district.

Board members should:

1. Require CPS schools only use instructional materials aligned with research-proven methods, such as the Science of Reading, which was the basis for the Mississippi Miracle.

2. Require more specific interventions at the district’s lowest-performing campuses to ensure student academic improvement, such as the Accelerating Campus Excellence (ACE) program, which is transforming student outcomes in Houston and across Texas.

3. Support a policy to renew high-performing charter schools no later than January (at least six months before contracts expire), giving families certainty and aligning with national standards.

Financial excellence at CPS

A district that can’t manage its own budget will eventually lose the right to manage anything else. And the first step to getting out of the district’s financial hole is to stop digging.

Board members should:

1. Transition to zero-based budgeting (ZBB) by Fiscal Year 2028, where every central office department, network office, and school must justify each line item. San Francisco schools use ZBB, as required by California law. In Philadelphia schools, ZBB recently identified $100 million in savings.

2. Pass a resolution calling on Springfield to require a state fiscal note and state pre-payment for any pension sweeteners that impact local school districts, as recommended by Mayor Johnson’s Financial Future Task Force.

3. Mandate a 14-member vote for all new borrowing: CPS currently requires only 11 votes for borrowing when included in the budget, but 14 votes at any other time. Given the district’s extreme debt load, there should be one standard.

4. Pass a resolution urging Illinois to opt in to the federal education donation tax credit to generate at least $100 million per year in additional funding to support services for CPS families, as New York and Colorado have done. This is especially important for CPS students with special needs.

Board excellence at CPS

If newly elected school board members expect excellence from the CPS central office, principals, teachers, school staff, and students, they must also hold themselves to a high standard of professional excellence.

Board members should:

1. Convene a Blue Ribbon Commission for CPS Facilities Planning,3 which should:

   1. Assess the current facility footprint.

   2. Establish an ongoing framework for optimizing school facilities for student success, including core principles of school utilization, neighborhood coverage, and model school staffing.

   3. Set a consistent minimum standard for schools in terms of enrollment and performance, as well as a consistent “high bar” standard that triggers school-model replication.

   4. Compare CPS’ capital financing ability to other large districts.4

2. The board has an opportunity to set a new standard for fairness and transparency in negotiations on CTU’s collective bargaining agreement, which begin in less than two years. This includes:

   1. Focusing negotiations on wages, benefits and conditions of employment (the traditional subjects of bargaining) and what is best for students.

   2. Considering changes to state law to increase board independence in bargaining.

   3. Using the zero-based budgeting process to identify any changes that are hampered by the collective bargaining agreement, and changes that are not.

   4. Opening up all bargaining sessions to the public (only presentations were open in 2024).

3. Adopt a policy requiring board members to complete annual continuing education in school finance and governance, (e.g. Georgetown Edunomics Lab offers a Certificate in Education Finance) with completion publicly reported and enforceable by fines/suspensions.

What Chicago voters should know

Without a clear plan entering office, new board members will be forced to react to several immediate crises and interest groups with outsized power.

That’s an outcome Chicago students can’t afford.

To ensure you receive a ballot for the November election and all future city elections, click here.

A Juneteenth celebration in Roseland ended in a mass drive-by shooting that left at least 14 people wounded.

It was the most horrifying moment in a stretch of violence that has pushed Chicago’s 2026 homicide count 8% above last year’s pace. Backsliding on what had been, until recently, an encouraging trend.

Days later, Mayor Brandon Johnson signed Executive Order 2026-3, establishing the Mayor’s Office of Gun Violence Reduction.

Here’s the problem: Chicago already has at least eight overlapping entities with some claim to police accountability or public safety coordination. And this executive order adds three more: the Office of Gun Violence Reduction, an Interdepartmental Gun Violence Reduction Cabinet, and a 17-member Gun Violence Reduction Advisory Council.

The executive order runs 11 sections and more than 1,500 words. But nowhere does it provide clear lines of authority between the new office and the bodies already in existence.

In fact, it gives the deputy mayor of community safety—who leads the mayor’s existing Office of Community Safety—a second, new role as executive director of the gun violence reduction office.

The root cause of Chicago’ public safety challenges has never been a lack of political bodies.

It’s the city’s failure to back professional solutions.

Chicago isn’t solving enough murders

Richard Day’s essential analysis last week at A City That Works shows the cost of Chicago’s poor police governance.

Fewer than one-third of homicides committed in Chicago in recent years have resulted in timely prosecution, compared to more than 80% in New York City.

Closing that gap requires witnesses willing to come forward. And witnesses come forward when they trust officers working their neighborhoods. So how does the city build trust?

Chicago doesn’t need to look far for answers. In fact, the analysis is done.

A 770-page workforce allocation study and a 167-page community policing assessment published earlier this year provide clear recommendations to improve community policing, such as beat integrity, consistent supervisory relationships, and ensuring officers have time for police work beyond chasing the radio.

But Chicago lacks the governance structure to quickly implement and monitor progress on these recommendations. In part because there are too many cooks in the kitchen. Compare that to Los Angeles, a city 50% larger than Chicago, which manages its police department through one primary, civilian-led body: the LA Police Commission.1

Chicago’s political instinct on public safety, every time something goes wrong, has been to add a body. The result is a city with a laundry list of public safety entities but just one in three murder cases ending in a prosecution.

Building a safer Chicago requires the bravery to break old habits, pick our heads up, and look around.

In the news

Mincing Rascals: I joined WGN Radio’s Mincing Rascals podcast to discuss the new Office of Gun Violence Reduction, the World Cup, and more (Apple Podcasts, Spotify).

More funding for Chicago students: Chicago public school families stand to gain at least $100 million a year in new education resources if Illinois Gov. JB Pritzker opts into a new federal tax credit program. I joined Patrick Pfingsten on WMAY to discuss.

Waiting for Superman: Civic Federation President Joe Ferguson invoked Chicago’s “waiting for Superman” syndrome in an excellent Crain’s piece on how City Council can govern itself more independently and effectively.

Digital asset transaction tax: I wrote last week on why Illinois’ new tax on digital asset transactions hurts Chicago. State Rep. John Cabello has now filed a bill to repeal the tax. Tell your state lawmaker to support the repeal here.

The canyon of LaSalle Street grew dark.

Thunder clapped. The wind howled. Amber-orange street lamps flicked on. And lightning flashed against the facade of the Chicago Federal Reserve, bouncing off its six-story Corinthian colonnades of Indiana Limestone.

But inside the Chicago Board of Trade, nobody looked up.

It was 2:30 in the afternoon. Markets wouldn’t close for another half-hour.

At an options trading firm on the fourth floor, dozens of traders sat glued to their monitors, clicking keys as quickly as rain hit the pavement.

Many of these traders were recruited to Chicago from faraway lands. Among their ranks were math olympiad champions, chess grandmasters, and physics professors.

But Frank was different. He grew up on the Southwest Side and started as a pit runner at the Board of Trade when he was 14 years old. He carried a thick Chicago accent.

Another thunderous boom rang out through the Loop. Frank turned his head. And he saw the majesty of a Chicago summertime thunderstorm, framed by 40-foot-tall windows.

He shouted out.

“It’s a [expletive] monsoon!”

What made Chicago rich

My first week on the job, Frank told me why those north-facing windows were so massive.

“They built ‘em like that for the grain.”

When the current Chicago Board of Trade building opened in 1930, the “cash grain” market was still important. If a miller wanted to buy a specific shipment of wheat or corn arriving by train, they needed somewhere to inspect physical samples. But incandescent lightbulbs cast an inaccurate color. So like an art studio, the Board of Trade needed north-facing windows with consistent, indirect sunlight throughout the day.

Instead of oil paintings, 36 long tables for grain inspection once sat beneath the same windows through which Frank watched the thunderstorm, 85 years later.

Those tables are no longer needed. And the reason why stands among Chicago’s greatest contributions to the world: it was home to the largest exchange in the West to transform physical grain into a commodity—graded, standardized, and reduced to a number that could be traded, modeled, and hedged.

This solved a trust problem for millions of people. Farmers could lock in a price before the harvest instead of gambling on a bad season. Millers could lock in a cost months before they needed the wheat. And grain merchants could borrow against a shipment without a banker ever laying eyes on it, because the grade stamped on the receipt was trusted as collateral.

It made Chicago rich.

Not just for the traders on LaSalle Street, but also for the immigrants, laborers, and tradesmen the boom employed. It is among the core reasons why from 1870 to 1900, Chicago grew faster than any city in world history.

The grain is long gone from the Chicago Board of Trade. So are pit traders like Frank. But a new generation of innovative financial businesses has been honoring the legacy of Chicago as a modern trading hub. And they are now butting up against a local culture older than Chicago’s trading pits: Illinois politics.

Springfield is threatening the city’s legacy of financial innovation. And the bounty that comes with it.

“First we get the money”

Allies of Chicago Mayor Brandon Johnson released a report the week of his inauguration in 2023 entitled, “First We Get the Money.” Among $12 billion in tax increase proposals highlighted by the report was a tax on every transaction at the Chicago Board of Trade.

Illinois Gov. JB Pritzker stepped in immediately to calm fears of a business exodus.

“We have a terrific financial industry in the state of Illinois,” the governor told Bloomberg at the time.

“We all understand that a financial transactions tax simply would encourage them all to … move their servers across the borders of the state to some other state.”

But last week, the governor signed into law a new transaction tax on digital assets. The first of its kind in any state.

New tax on digital asset transactions

Pritzker signed the Illinois state budget last week. It included the Digital Asset Tax Act, a 0.2% tax “on the value of any digital asset exchanged, transferred, or stored on a customer’s behalf by a broker doing business in Illinois.”

Notably, this tax was introduced just hours before state lawmakers passed the $56 billion state budget at 4:13 a.m. on Monday, June 1.1

Industry leaders locally and across the country were shocked:

• “This Illinois law is remarkably bad - it will end up hurting the state, kill jobs and push innovation out of the state.” – Brian Armstrong, Co-founder and CEO of Coinbase

• “This is like taxing changing your bank password.” – Hayden Adams, founder of Uniswap

• “Chicago has a real opportunity to lead in stablecoins / trading infra / programmable payments. There are countless startups and companies in the state creating high $$$ jobs and building the next generation of financial infrastructure. Most people won’t notice a 0.2% tax on a handful of transactions. But if the future is millions of machine-to-machine payments powered by stablecoins, every layer of friction matters.” – Landon Campbell, Chicago tech investor

• “I would like to remind everyone in crypto law that as defined in the bill, this likely covers all forms of digital money, so if IL is not enforcing this against electronic bank transfers, you should sue.” – Austin Campbell, NYU Stern School of Business Adjunct Professor

• “You aren’t taxed if you exchange a stock, bond, or derivative in paper form, but you are taxed if they happen to be recorded on a blockchain? That’s like taxing email.” – Miles Jennings, general counsel for a16z crypto

Illinois commonly relies on “sin” taxes to stitch up budget gaps. Cigarettes, gambling, and alcohol are all politically easy targets for tax hikes. “Crypto” is now among these. The industry has become politically polarized, owing in no small part to members of the president’s family pulling in billions of dollars from it.

But this tax goes far beyond scammy meme coins pushed by politically connected figures. And it goes beyond Bitcoin. It threatens to destroy an ecosystem of financial businesses in Chicago relying on new technology to better serve their customers.2

To an average person, a 0.2% tax seems minuscule. But to Chicago businesses built on facilitating billions of financial transactions using modern technology, it is a monsoon.3

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The tax is only estimated to bring in $60 million. That is a rounding error in the Illinois budget. But because no other state imposes a tax like this, Illinoisans should not be surprised if this costs the state more tax revenue than it brings in, as businesses in this space decide to invest their time and talent elsewhere.

Unless something changes.

What you can do to stop the digital asset transaction tax

This tax does not take effect until Jan. 1, 2027. And Illinois lawmakers will return to Springfield for veto session this fall.

The tax will almost certainly be in court before then. But with enough engagement from constituents, Illinois state lawmakers could be convinced to make reforms on their own.

To tell your Illinois state representative to repeal the digital asset transfer tax, click here.

The U.S. men’s national soccer team opened the 2026 World Cup Friday night with its greatest performance in modern history: a 4-1 drubbing of Paraguay.

But the tournament is a spectacle Chicago won’t be part of.

And the former mayor who made that call wants you to know he was right.

“We were on the front end of the bad side and the back end of the good side,” Rahm Emanuel told The Athletic.

“I said, ‘I don’t know what any other mayor or governor is doing, but do you expect me to treat the Chicago taxpayers as the dumb money at the table? You’ve got to be kidding me!’”

He wasn’t wrong. Emanuel read the deal correctly.

Here’s the problem: The call was his alone to make. And it’s only a matter of time before another deal, forged in secret with private interests, comes along.

Decision made in secret

The specific clause that broke the deal, according to the former mayor: FIFA insisted the contract include the right to demand a dome be built over the open-air Soldier Field.

When Emanuel told them to remove that clause, FIFA replied they never exercise it but couldn’t take it out.

“So I said there is not a chance I am going to have you directing me on a $50 million-$100 million expense to the taxpayers. That was the straw that broke the camel’s back,” according to Emanuel. “You can’t have something in there that leaves the city and the taxpayers exposed, where (FIFA) gets to decide it and I have no vote in it.”

The former mayor is right. This was a bad deal that could have committed Chicago taxpayers to hundreds of millions in open-ended obligations.

But it was being evaluated, negotiated, and ultimately rejected entirely within the mayor’s office.

At the time, Ald. Scott Waguespack called on the Emanuel administration to release the complete terms of the FIFA proposal and provide projections on the financial impact — noting pointedly that there had been “no discussion outside of the fifth floor.”

That Emanuel made the right call is worth crediting.

But the governance structure that allowed him to make that call unilaterally is the same structure that has produced some of the worst financial decisions in Chicago history.

A pattern Chicago keeps repeating

Consider the city’s pattern of poor deals with private entities for their use of public infrastructure:

• Parking meters: In 2008, Mayor Richard M. Daley rammed the 75-year parking meter deal through the city council in 72 hours, costing Chicago billions.

• Olympics: In 2009, Daley reversed his promise that Olympic hosting wouldn’t cost Chicago taxpayers a dime, signing a contract with the International Olympic Committee that put the city on the hook for any losses — with at least $1.75 billion in exposure.

• NASCAR: In July 2022, Mayor Lori Lightfoot announced a three-year deal handing NASCAR the streets around Grant Park. Aldermen representing the wards affected by the deal were “purposefully and specifically excluded from any discussion” before the contract was signed, and only learned the terms when reporters obtained the document via FOIA. One alderman noted the city would receive less than $1 million from NASCAR for tying up downtown and Grant Park for more than a week — a fraction of what Lollapalooza pays annually for a comparable footprint.

As Ed Bachrach and I wrote in the Chicago Sun-Times, this pattern has a name. The practice of granting private parties the use of public property is called a concession. And Chicago has done a horrible job of managing those concessions:

All concessions involve a tradeoff between the public’s access to their public property and some other public interest. In Chicago, however, there is no mechanism to give weight to the public interest. The private concession almost always wins.

When the concession is conspicuous and egregious, like the parking meters and Grant Park, citizens and journalists ask all the proper questions. Why was this concession approved and others rejected? What were the alternatives? How were the terms determined? Was the public interest taken into account? What is the value of common use?

These vital questions are not publicly answered in Chicago, because they are always too late. The deal is cut in secret. And then, if City Council approval is needed, it is rammed through.

The FIFA host city agreement was on track to follow a similar pattern. No independent review. No public deliberation. Just whatever the fifth floor decides.

A better way to handle concessions

New Yorkers enjoy greater protection over their public assets than Chicagoans. That’s owed to New York City’s Franchise and Concession Review Committee, which:

• Reviews and approves concession terms before they’re final.

• Requires public notice, hearings, and a minimum 15-day comment period for concession deals.

• Publishes annual concession plans that include every concession action planned by every city agency, so the public can see what’s coming before negotiations even begin.

• Is not entirely captured by the mayor: While the commission is primarily made up of mayoral appointees, the independently elected comptroller also sits on the commission. And borough presidents get to vote on deals that affect their communities.

This structure is baked into New York’s city charter. Chicago does not have a charter, and requires a change in state law to adopt one.

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Short of a charter, Chicago City Council should establish a standing concession commission with authority over these kinds of arrangements, requiring public proceedings before deals are signed.

Until then, Chicago’s protection against bad mega-deals is a mayor with good judgment.

That’s what ensured FIFA didn’t take advantage of Chicago.

But next time, private interests could slip a bad deal past the keeper.

In the news

Update on opting in: Readers of The Last Ward know why Illinois should opt in to the new federal tax credit for education donations (“How Democrats can unlock $100M+ for Chicago education without tax hikes”). But the Chicago Teachers Union has urged Gov. JB Pritzker to stay out, calling the program “a scam designed to undermine public education.”

Notably, one of the most prominent voices against private school vouchers, Michigan State University Prof. Josh Cowen, just came out in support of opting in.

“I’m not willing to leave public school families and public school educators alone on the road we’re heading down by telling them there’s nothing in the federal scholarship for them,” Cowen wrote.

Mayoral candidate pushing common sense reforms: Chicago mayoral candidate Liam Stanton published his campaign’s “Common Sense Government Reforms” platform last week, including changing the city’s election timing and creating a city charter.

Teen takeovers: Teen takeovers may be the most prominent public safety topic in Chicago. Political consultant Sabha Abour recently interviewed two young men who have been organizing them — it’s worth your time.

And here’s what Chicago can learn from Washington D.C.’s successful response to teen trends.

For the first time in 30 years, Chicagoans will vote on a fully elected school board in November.

But who will be on the ballot? Well, that’s a legal matter. Under dispute.

Because in Chicago, securing your name on the ballot can often prove more difficult than winning at the ballot box.

Every election season, lawyers trained in the dark arts of signature challenges spend weeks in the basement of the Chicago Board of Elections, working to kick candidates off the ballot.

This installment of The Last Ward examines the drama surrounding candidates for school board, a legislative plot to rewrite petition signature requirements, the ruthless nature of signature collection, and how one city successfully dismantled byzantine ballot challenges and the rampant fraud that comes with it.

Why more than half of Chicago school board candidates are facing petition challenges

Chicago school board candidates have been passing petitions for months to get on the ballot.

State law sets the rules for gathering those signatures, which candidates had to file with election authorities by May 26.

But on May 30, a curious piece of legislation appeared in the waning hours of Springfield’s legislative session: An amendment to an elections omnibus package, the bill would have retroactively changed the rules about who was eligible to circulate petitions on behalf of Chicago school board candidates.

The package did not pass. But the Chicago Teachers Union lobbied for that amendment, according to Statehouse sources, suggesting that the union had problems with the signatures they gathered for their preferred school board candidates.

Indeed, 28 of the 51 school board candidates are now facing petition challenges, including many of the candidates supported by the union.

Notably, CTU did not file challenges against any candidates. The union even claimed it was unfair to do so. President Stacy Davis Gates said she “wanted to see more people on the ballot, not less.” But that rings hollow, given the union used petition challenges to kick 12 school board candidates off the ballot in 2024, according to Chalkbeat Chicago.1 In fact, the union hired the same election attorney their opponents are using today: Michael Kasper.

The CTU’s push to change the rules retroactively—helping the union’s political machine while hurting those who followed the law—was unfair and undemocratic.

But state lawmakers should change the rules going forward. Here’s why.

The nightmare of signature gathering in Chicago

A Chicago voter seeking to kick a candidate off the ballot files an objection to that candidate’s petition signatures with the Chicago Board of Elections.

There have been more than 2,100 of these filings in Chicago’s municipal elections alone since 1983, according to WBEZ analysis.

Some of the specifics are absurd:

• An average Chicago municipal election sees more than 180 objection filings.

• In 2011, there were more objections filed (428) than candidates (380).

• In 2015, half of candidates who filed faced objections and one-third were removed from the ballot

• In 2019, nearly half of candidates faced objections, and one-fifth were removed.

Each filing typically comes with several hearings in front of a hearing officer, often taking weeks. The officer then makes a recommendation to the election commissioners on whether the candidate has enough signatures to remain on the ballot.

Petition signatures can be ruled invalid for a number of reasons, here are just a few:

• The petition pages weren’t properly bound together

• The petition pages weren’t numbered

• The signer printed their name rather than writing it in cursive

• The signer wrote their address incorrectly

• The signer already signed another candidate’s petition

• The volunteer or paid staffer gathering those petitions was ineligible to do so, making all the signatures they gathered invalid

• The petition circulator did not properly sign their name on the petition page, making that entire page of signatures invalid

No media better describes the dark underbelly of the petition challenge process than City So Real. Director Steve James’ five-part documentary miniseries explores Chicago through the lens of the 2019 mayoral election, and follows candidates into the basement of the Board of Elections.

“I had no idea just how Byzantine and ruthless it could be,” James said.

“Chicagoans, particularly of the political class, love to brag about how tough Chicago is politically. I don’t know that that’s something we should be bragging about… Politics is a tough game no matter where you are, but what makes it tough in Chicago doesn’t necessarily make for great leadership and great governance, because what often comes with that is backstabbing and gamesmanship and corruption.”

Here’s the good news: This is an easy fix.

A better way to get signatures

Chicagoans are familiar with political operatives flagging down pedestrians with clipboards and paper.

But for the last decade in Denver, candidates for office can collect digital signatures on an iPad with an app called eSign. That app automatically checks whether the person entered the correct information and is eligible to sign, and then securely uploads those signatures directly to the election authority.

The results are stunning.

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In Chicago, roughly half of signatures are ruled valid after adjudication. And in Denver’s old paper system, that rate was about 70%. Today under eSign, 97% of signatures are valid.

This change has severely reduced the cottage industry of election attorneys. It’s also cut down on fraud—a common problem among campaigns using paid petition circulators.

“Forging voter signatures on candidate nominating petitions for elected office remains, unfortunately, one of the most common illegal tactics of unscrupulous campaigns or individual petition passers,” according to Chicago-area election attorney Michael Del Galdo.

If a candidate files fraudulent signatures—knowingly or unknowingly—it is unlikely those will be caught without a challenge.

Denver’s system virtually eliminates that problem.

Changing state law

In his 2018 exit interview, Cook County Clerk David Orr put ballot access at the top of his list for needed reforms.

“The Denver Elections product, called eSign, is ready for Cook County,” he told WTTW. “Like Election Day Registration, this can be piloted in Cook County so we can refine it for all of Illinois.”

State Rep. Kelly Cassidy, D-Chicago, filed House Bill 4966 in 2022. The bill would have allowed local election authorities to copy Denver’s example.

It didn’t pass. But lawmakers should revive the effort.

Pass fair rules. Stop the petition scammers. And get more Chicagoans on the ballot in local elections.

In the news

Last week’s edition of The Last Ward examined what Chicago could learn from Washington, D.C.’s response to “teen takeovers.” I joined WGN Radio to discuss those findings (Apple Podcasts, Spotify). Chicago mayoral candidate Susana Mendoza also cited D.C.’s example.

In other news, The Last Ward was first to report Chicago Teachers Union leadership had lost a vote to hike member dues by $8.5 million. We now know the final results of that election: 63% of members voted no, representing a 26-point loss for union leadership.

From dinner table conversation, to City Council debates, to mayoral press conferences, teen takeovers may be the most prominent public safety topic in Chicago.1

Recent high-profile teen takeovers, also known as teen trends, include:

• A November 2025 incident near the Chicago Theatre during the Millennium Park tree-lighting that left a 14-year-old dead and eight others wounded in two separate shootings.

• A March 2025 incident in Streeterville left a 15-year-old grazed by a bullet, with officers logging 12 arrests for battery against police, resisting arrest, and possession of a replica firearm.

• A May 2026 incident on the Near West Side where hundreds of teens gathered ended when an 18-year-old drove his car into five police officers. He is now charged with attempted murder.

Of course, many young people participating in these trends lack consistent access to fun, safe events. And any sustainable response to teen takeovers requires work to address those disparities, including through city-funded programs.

But frustration has been brewing for more than two years on this topic due to a repeating cycle that leaves Chicagoans without resolution:

1. A teen takeover gets out of control, causing disorder and violence.

2. City Council calls for law enforcement reforms to better manage these trends, typically involving curfews.

3. Mayor Brandon Johnson rejects the Council’s push, and highlights the need for city spending on programs for youth.

This cycle lacks curiosity, driven by two simple questions. Beyond investing in youth programs, what law enforcement tools have other big cities used to effectively respond to this phenomenon? And what can our city learn from their experience?

Chicago is not alone in facing teen trends, after all.

Washington’s experience is worth considering.

Lessons from D.C.

In Summer 2025, Washington’s Navy Yard neighborhood became a focal point for the D.C. version of Chicago’s teen takeover problem — repeated large gatherings that spurred violence in one of the city’s busiest dining and nightlife districts.

After a particularly chaotic Independence Day weekend in 2025, Mayor Muriel Bowser and the D.C. Council had seen enough.

Working together, they created a new tool: extended juvenile curfew zones.

Here’s how the zones work:

• A juvenile curfew zone is a defined geographic area where the police chief can impose an earlier, stricter curfew: no gatherings of nine or more minors in any public place beginning at 8 p.m.

• Zones last up to four days and must be declared based on cause: either recent crime in the area or credible intelligence about a planned gathering likely to endanger public safety.

• Police must issue at least two verbal warnings before taking enforcement action.

• Violations are civil infractions, not criminal charges.

Here’s a brief history of how the zones have been implemented so far, and the initial results:

• July 7, 2025: The D.C. Council passed emergency legislation introduced at Bowser’s request (Juvenile Curfew Emergency Amendment Act of 2025). This gave the police chief authority to declare extended juvenile curfew zones, among other changes. In D.C., emergency legislation expires after 90 days.

• Summer 2025: D.C. Police Chief Pamela Smith declared seven curfew zones between July and August. The city reported zero violations during active zone hours and hailed the measure as a success.

• Oct. 5, 2025: The emergency legislation expired. And within weeks, disorderly gatherings returned.

• Nov. 4, 2025: In response, the Council passed first reading of legislation keeping the curfew framework alive through April (final passage Dec. 2).

• Feb. 12–April 15, 2026: Once the law took effect, the chief of police declared 14 curfew zones resulting in just seven total violations — a figure the city cited as evidence the tool was working.

• May 5, 2026: The Council passed legislation permanently codifying the police chief’s curfew zone authority. The law will take effect in July after a mandatory congressional review period.

• May 22, 2026: With the temporary act expired and the permanent law still weeks away, Bowser issued a new executive order restoring police authority to declare juvenile curfew zones through June 6, 2026. A gap between June 6 and mid-July, when the permanent law kicks in, may require another bridge order.

Of course, this single enforcement tool is not enough to permanently solve the issue of teen trends.2 But to the extent results can be measured, they are encouraging. What D.C. has shown is that the political coalition for this tool can hold. And it can continue to evolve in response to changing circumstances.

Adopting D.C.-style reforms in Chicago

Chicago Police Superintendent Larry Snelling spent much of his recent appearance at the City Club emphasizing the need to respond appropriately to teen takeovers.

Snelling is not alone. Illinois State Rep. Kam Buckner, D-Chicago, highlighted the issue this way in a recent interview on the Fran Spielman Show: “Accountability is not the opposite of love. Accountability is part of love and we ought to start acting that way.”

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Chicago City Council should consider a three-month pilot program similar to D.C.’s. Results should be reported back to the Council’s public safety committee on a consistent basis. And if it’s working, extend it.

Beyond responding to teen takeovers, two landmark reports point the way to professional excellence in the Chicago Police Department. One of the most stunning findings in those reports is that CPD has no clear, department-wide framework guiding how officers are expected to engage with the public in everyday interactions.

And of course, the city should continue investing in and measuring the outcomes of its youth programming.

As I wrote in City Journal last year, one of the most painful parts of the new Chicago pension sweeteners signed by Gov. JB Pritzker is that they will cost more money in 2026 ($60 million) than the city’s entire summer youth jobs program ($52 million) —ballooning to $753 million a year by 2055.

Despite his support for the youth summer jobs program, Chicago Mayor Brandon Johnson said nothing publicly against those sweeteners as they moved through Springfield.

In the news

The Wall Street Journal published my take on New York City Mayor Zohran Mamdani’s city budget proposal: “Capitalism Delivers for Zohran Mamdani.” The piece highlights how Mamdani’s city budget relies heavily on cuts to pension payments made possible by strong stock-market returns.

The Wall Street Journal editorial board also cited the Chicago Policy Center in their piece on Chicago Teachers Union members’ rejection of a proposed $8.5 million dues hike for politics (“A Union Dues Rebellion in Chicago”), as first reported in The Last Ward.

I joined the Mincing Rascals podcast on WGN Radio last week to discuss a variety of federal, state, and local issues (Youtube, Apple, Spotify).

And I joined Sarah Schulte on ABC 7 to discuss Brandon Johnson and Chicago Teachers Union President Stacy Davis Gates traveling to Rome during the waning days of legislative session in Springfield.

Chicagoans just witnessed a watershed moment in the city’s political history.

Chicago educators have dealt a stunning rebuke to Chicago Teachers Union President Stacy Davis Gates’ push for an $8.5M dues hike.

“With approximately 80% of schools counted, if current voting trends hold, roughly 60% of members voted against moving forward with this proposal right now,” according to an internal announcement sent to members.

In modern Chicago history, there are no examples of teachers union membership bucking leadership in a referendum of this magnitude.

As first reported in The Last Ward, CTU leaders cited political spending as the No. 1 reason for the proposed progressive dues hike, despite the union handbook’s insistence that member dues money is not used for political spending.

Gates’ announcement did not report results on the second question on the ballot. That initiative would have restricted members’ ability to sue the union.

Given the dues hike vote, it’s likely members rejected the second proposal as well.

Reaction to the vote

Our team broke news of the dues hike vote yesterday. Here are a few notable reactions:

• “The fact that CTU members rejected a PROGRESSIVE dues hike is quite remarkable.“ – Rich Miller, CapitolFax

• “Wow!“ – Mary Ann Ahern, NBC 5

• “Huge news. Serious questions remain about how the Chicago Teachers Union can raise millions to fund candidates in 21 school board districts, re-elect Mayor Brandon Johnson, and defend its 20-some hard allies on the City Council.“ – Political consultant Frank Calabrese

• “Potentially a very big deal. CTU already faces an uphill battle for the school board and to re-elect Mayor Brandon Johnson. If they’re not able to raise more money, they’re in much deeper trouble.“ – Greg Pratt, Chicago Tribune

• “Well done.” – Illinois comptroller and likely Chicago mayoral candidate Susana Mendoza

Just as meaningful were the reactions from Chicago educators. Here are just a few texts from teachers on Saturday, following the announcement:

• “Email from CTU!! The members have spoken!!! Woohoo!!!”

• “I’m so happy they finally lost.”

• “They’re acting as though it’s because members just didn’t understand. We do understand, they’re simply wrong.”

Veteran Chicago teachers like Ifeoma Nkemdi have worked to hold union leadership accountable for years. And faced harassment, ridicule, and false accusations as a result.

“Sometimes people fall in love with fighting,” Nkemdi said in the documentary Local 1. “That’s when I started to feel unmotivated to continue supporting the [CTU] agenda, because I just felt like they really enjoy fighting.”

Teachers like her were vindicated by this vote.

What this means for CTU leadership

Under Gates’ leadership, CTU has quadrupled its political spending.

The union and its affiliates were the No. 1 spenders on Chicago politics in the 2023 municipal elections. And in fiscal year 2025, the union spent over $4.2 million on “political activities and lobbying” — a record high since CTU started filing annual reports with the U.S. Labor Department, according to analysis from Mailee Smith at the Illinois Policy Institute.

Meanwhile, the union spends just 18 cents of every dollar on teacher representation.

Consequences of this vote for CTU’s political leadership include:

• Gates will have fewer resources to back CTU’s own political staffer, Hilario Dominguez, in his run for school board president this November.

• The same is true for Mayor Brandon Johnson, should he run for re-election in 2027.

• Chicago City Council members will be less likely to vote with the mayor, given his top backer’s reduced capacity to fund Council races.

• With petition signatures equivalent to 5% of membership (roughly 1,500 signatures), CTU members can send their own referenda to a union-wide vote. Given the dues hike vote, members may be encouraged to push referenda offering greater protection against the use of their dues money for politics, for example.

• Gates also serves as president of the Illinois Federation of Teachers. There will now be increased scrutiny from teachers statewide on the use of their dues money for Chicago political races, given local members rejected a dues hike for that purpose.

Local polling and political races have increasingly shown CTU’s leadership has grown toxic.

Indeed, CTU lost five of six races for school board in which the union and its affiliates spent more than $250,000 for their candidate.

For the last decade, Gates and her allies have been building a political machine fueled by members’ dues.

Teachers just sent the bill back.

In the news

I joined WTTW’s Chicago Tonight for a debate with Chicago Public Schools Board Member Michilla Blaise on the causes of Chicago Public Schools’ $732 million budget deficit, and potential solutions.

Blaise was originally appointed to the board by Johnson and is running for election in November.

Watch the full debate here and read WTTW’s story here.

Chicago Magazine ran a provocative piece by Edward McClelland last week, titled “The Progressive Slide.”

“It wasn’t all that long ago that progressives had the momentum on City Council,” McClelland wrote. “Fast-forward to this March. They are no longer in control of the agenda. Instead, they’re playing defense, trying to protect what they already gained.”

McClelland’s piece centers on Council’s 19-member Progressive Reform Caucus.

But the backslide among six aldermen who are self-described democratic socialists—those who composed what Jacobin described as Council’s socialist wave in 2019—is perhaps more striking. Not only for that faction of the council, but also for the organizing force they represent. Or what is left of it.

In an hour-long interview for the new podcast from Fox Chicago’s Grant Horne, I ran through the rise and fall of Chicago’s democratic socialist political project, and how it compares to those in cities like New York and Seattle.

You can watch the full episode here.

Below are a few excerpts, edited for clarity.

On running as a socialist for Chicago City Council:

Grant: Well, let’s talk about elected people now .. when you see these six [democratic socialist] elected leaders, what comes to mind when it comes to their presence within City Hall?

Austin: What’s so interesting about this dynamic in Chicago [are] the intentions versus the outcomes. What does it look like if your goal is European-style social democracy, but you’re elected to City Council of Chicago? What levers do you really have to bring that about? You don’t have a lot. And in fact, Chicago, even differently than a lot of other big cities, council members very rarely are true legislators. They’re more like customer service representatives in their ward. Most of their time is spent responding to constituent concerns about potholes or tree trimming or parking or sidewalk cafe permits or business signage—sort of ticky-tack things. So one of my arguments for wholesale reform of the structure of government in Chicago, which is a deeper conversation, is that even folks who are elected on a pretty far-left platform, they have no way to really do anything that they thought they were running to do and what people thought they were voting on them to do. Again, I think when you’re in City Council, it’s not built to be a true legislative body. So it ends up that a lot of [actions] end up being more performative things—like resolutions, or it could be simply proposing really wacky tax hikes, which that’s not good, that scares people away. Even just the proposal of those things. But they feel like they were elected to maybe push some of that forward.

Former Uptown Ald. James Cappleman later weighed in on this argument.

On Chicago Mayor Brandon Johnson and delivering on an agenda:

Austin: We’re at a unique point in Chicago history because there’s never been a sitting mayor who was as unpopular as Brandon Johnson was midway through his first term. And that fractured his coalition tremendously. I think the Chicago Teachers Union is essentially in his corner and nobody else is, including many of the [Democratic Socialists of America, or DSA] members of City Council. So in Chicago, I think that has essentially put things at a standstill. Brandon Johnson has not had major policy changes passed really in the last two or three years in part because of that. He was not able to, once he got into office by a very slim margin, expand his coalition. Rather, partially because of these ideological purity tests, that coalition only shrank after he got into office.

You look at someone like [Seattle Mayor] Katie Wilson when Starbucks and Howard Schultz left—what then? This glib remark: “Bye.” You can get by on that maybe for a couple of days on social media, but then what happens when you have to balance a budget? You’re going to hike property taxes on everybody? Are you going to have to ask the state to pass a new, novel tax on certain types of people? What kind of political capital do you have to get that done? With [New York City Mayor Zohran] Mamdani, you see a ton of interaction between him and the state that’s very interesting because there’s only so much he can do as a mayor. When is Mamdani going to start blaming [New York Gov. Kathy] Hochul? He already has a little bit. When is Brandon Johnson going to start blaming [Illinois Gov.] JB Pritzker? He has a lot. Wilson, I’m not as familiar with, but that will happen. It’s the posture of resistance. That is what the DSA is incredibly good at. But it doesn’t work well when you’re actually in power.

On the political muscle of the DSA in Chicago:

Austin: There is DSA organizing energy, but the money is only going to be able to come from government-sector unions. Members of DSA are not going to be spending millions of dollars on politics. That money is coming from groups like the Chicago Teachers Union. And where I think DSA-like politics are perhaps most effective is in organizing within government-sector unions. Most people are not focused on the politics of their union; they’re just going to work as a teacher or as a bus driver or a train conductor for the CTA. They’re not really thinking about union politics. But if this is your ideology, you can effectively organize a caucus within that union, take over the union, and then you have tens of millions of dollars to play with every year. And that’s what you see in Chicago …

We can vote out Brandon Johnson in Chicago, but none of us get a vote on the president of the CTU, and they’re the ones who are really wielding a ton of money and juice in these elections …

There is a caucus within CTU called CORE—the Caucus of Rank and File Educators. And that was started as essentially a socialist or critical theory reading group within CTU. And it had people like Jackson Potter, Karen Lewis, Stacy Davis Gates, later Brandon Johnson. And that reading group was more sort of affiliated with the types of politics that you would see with a DSA. So I would say birds of a feather for sure, and aligned almost 100% on the types of candidates that they’re backing. So almost every socialist candidate for city council is also endorsed by the Chicago Teachers Union, and gets funding from the Chicago Teachers Union.

On New York City Mayor Zohran Mamdani singling out Citadel CEO Ken Griffin in a viral video promoting his pied-à-terre tax:

Grant: It seems like [Griffin’s] going to move the rest of his New York operation to Miami. So after leaving Chicago and taking a large part of Citadel with him there, it seems like Citadel is just going to be a Miami-based organization … this could be a gigantic one-man rug pull for the city of New York to pay for a lot of these very ambitious things that Mamdani had promised. Is that enough to crater the aspirations of a city? Do you think that Griffin’s move will act as like a domino where it might get more people at least thinking about the process?

Austin: It’s very hard to kill a big city. There are so many advantages. I was just in New York City on Sunday; I rode the Five Boro Bike Tour. It was a 40-mile bike race, they closed down the streets. Mayor Mamdani was doing it. And as you’re riding around New York City, [you are struck by] hundreds of years of accretive human innovation and ingenuity and activity to build what New York City is. You cannot wipe it away with a few political videos. That’s not going to happen. That said, I live in Chicago and I lived here when Ken Griffin lived here and I live here now when he doesn’t. And every highly successful person in Chicago knows Ken Griffin left, and knows why he left, and has empathy for why he left. I’m very grateful for all of the Chicagoans who stay here and make the city better and fight. [But] all of those people, when they look at what Ken Griffin did, say, “Yeah, I get it.” I ride the bike path that Ken Griffin helped pay for on the Lakefront Trail. I go to the museums that he contributed to. He was just an incredible philanthropic force in our city. And having that energy leave and go somewhere else, it’s really sad. Cities shouldn’t discount what happens when those sorts of nodes leave. And that’s really the difficult thing when talking about these really small bands of taxation where it’s like, “everybody over $1 million,” “everybody over $10 million,” “everybody over $100 million.” You lose just a few of those people and it’s sort of a social contagion—like, a lot more could leave. So I don’t think it’s going to tank New York City finances overnight, but the more progressive your tax structure, the more that hurts [when high-earners leave] because those people are bearing a bigger part of the load. That’s why you don’t see that kind of thing in European-style social democracies; it’s a much broader base [paying higher taxes].

On whether to bet on Chicago:

Grant: Last question: are you “short” or “long” on Chicago? I’m long. I think that we have a great infrastructure, we have great natural beauty, we have a great story. We’re a beautiful natural magnet for all the cool people that live in the plains and in the Midwest and in the South. I feel like when the rest of the country becomes uninhabitable because of mudslides or power outages or shorelines or things along those lines, that the Midwest is going to look really “hot” from a real estate perspective, maybe like in the next 10 or 15 years. So that informs my attitude about why I’m long on Chicago. How do you feel?

Austin: I think the climate refugee argument is a form of what I would call “Waiting for Superman” syndrome, where it’s like, “Well, this thing completely outside of our control [as a city] actually is going to break our way and that’ll be our saving grace.” I think I’m actually much more hopeful than that because I agree—I think Chicago is the greatest American city and happens to be the worst governed. And this is a good thing because our problems are man-made problems. We do not have a plague of locusts, we do not have hurricanes, we do not have earthquakes. All of our problems are man-made, which means the solutions are man-made, and those can change much more quickly than natural problems that are working against you and they can be changed. So I’m very long on Chicago.

That and much more in the full interview.

“Has your brand become toxic?”

This was a pointed question from WGN Political Editor Tahman Bradley, posed to Chicago Teachers Union President Stacy Davis Gates in a recent interview.

Her immediate response: “I don’t understand the question.”

When pressed, Gates added, “The Chicago Teachers Union is not a political party, it is a labor union.”

But internal union documents show CTU leadership is trying to skim $8.5 million more from teacher paychecks explicitly for politics, while trying to silence union members critical of Gates’ leadership.

Under the proposed dues hike, Chicago teachers would see up to $800 more per year flow from their paychecks to union coffers. The union already takes in more than $40 million a year, mostly from dues. And it spends less than 18 cents of every dollar on teacher representation.

The No. 1 reason for the proposed dues hike? Politics.

“We must win a majority of the first 21 person fully elected school board in November,” reads the first point in CTU’s member FAQ document.1

This directly contradicts CTU’s promise to members about how leadership uses dues money.

The official CTU handbook tells members that the union does not use dues money for politics, so if they are interested in funding political activity, they should consider voluntary donations to CTU’s political action committee.

“Our dues are not used for political purposes,” according to the handbook. “So our PAC relies on extra contributions from our members to support progressive candidates and to impact elected officials at the city, county and state levels.”

This kind of double-speak is one reason members are concerned about another constitutional change slipped into the dues hike vote, which will take place on May 20-21: an attempt to stop members from holding the union accountable.

A proposed amendment to the union constitution tries to place limits on when members may bring a lawsuit against the union for violating members’ rights.

This provision is clearly a response to members’ lawsuit against union leadership regarding Gates’ years-long refusal to publish audited financial statements. The judge in that case has repeatedly denied the union’s attempts to dismiss it.

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Teachers opposed to these changes have been circulating this flier, urging members to vote no.

What will CTU members get in return for millions of dollars in additional dues?

If the 2024 school board elections are any indication—not much.

Results of CTU spending on school board races

CTU leadership’s record on school board races may not inspire confidence among members.

A Chicago Policy Center analysis of a dozen affiliated PACs found CTU spent nearly $2.9 million on school board races in 2024. Of that spending, more than $2.1 million (75%) went to losing candidates.

And while CTU-backed candidates lost six of the nine competitive seats overall, they fared worse in their biggest-spending races, losing five of six contests in which the union and its affiliates put up more than $250,000 for their candidate.

The Chicago school board elections take place Nov. 3.2

Is another $8.5 million enough to clean up a toxic reputation? Not likely.

In the news

Update on federal tax credit scholarship: Last week, Democratic New York Gov. Kathy Hochul said she plans to opt into the federal tax credit scholarship program. If Illinois Gov. JB Pritzker follows suit, Illinois could unlock $1 billion in donor money statewide for both public- and private-school students. If Illinois does not opt in, that money will flow to other states. The Last Ward reported in February on how Illinois Democrats could unlock at least $100 million in new resources for Chicago public-school students by opting in.

Update on the investigation into how Chicagoans learned about a meeting to hike their property taxes: The Last Ward reported in January on an absurd, taxpayer-funded investigation into how local media learned of a planned Chicago school board meeting to hike the district’s property tax levy. That investigation is now complete. Lawyers interviewed two dozen witnesses, and found nothing.

Update on Illinois’ muni debt crisis: My colleague Joe Tabor last week published a must-read piece in Crain’s Chicago Business about how Illinois recently rejected south suburban Harvey’s request to be designated a “distressed city.” The saga shows why the state must implement a better structure to assist insolvent local governments, including allowing for the option to pursue debt relief via Chapter 9 bankruptcy. The Last Ward reported in October on how Harvey is tipping the first domino in Illinois’ municipal debt crisis.

Mincing Rascals: I joined the Mincing Rascals podcast on WGN Radio to discuss the SAFE-T Act, the millionaires tax, and more. My “green light” recommendation: Force Majeure (2014).

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.