Austin Berg wanted to talk about structure before we talked about anyone’s name. We sat down in Lincoln Square on a summer afternoon. The problem, in his telling, is the shape of the government itself, more than any one mayor.

Berg has spent a decade on that argument. He runs the Chicago Policy Center, an arm of the free-market Illinois Policy Institute, writes The Last Ward to more than 158,000 subscribers, and co-wrote The New Chicago Way. What he wanted to litigate was the machinery.

“Among the big cities, we have the most vestiges of a strongman, almost caudillo, sort of system,” he said. A weak council, often seated by the mayor. No city charter. No elected finance officer or city attorney. No public vote on debt or taxes. Among big cities, Chicago stands out for having none.

Waiting for Superman

I asked whether the 2027 mayor’s race matters or whether it is a field competing to run a broken machine. Berg has a name for the reflex behind the question.

“The mayor’s race is the lens through which Chicagoans understand city politics more than anything else,” he said. “This is a pathology.” He calls it waiting for Superman. The city looks to one person for salvation because the strong-mayor system trained it to.

The office matters to him. What the city gets wrong, he says, is what it expects the office to do. “It’s a necessary condition to have good leadership,” he told me. “It’s not a sufficient condition to have a growing, thriving city.” The candidates he watches for are the ones who ask a longer question.

“Public office does not create intellectual capital. It consumes intellectual capital.”

Most people who run for mayor arrive without much of it, he said, because the way the city actually works sits below the headlines. His group briefs candidates across the spectrum on their real options. The ones who stand out, in his telling, ask what they can build now that leaves the city stronger on its 200th birthday in 2037, whoever holds the office by then.

The $11 billion

To see the structure work, Berg said, look at last year in Springfield. A pension sweetener added about $11 billion in liabilities to Chicago. The immediate annual cost he put at $30 to $50 million, enough to double the city’s summer jobs program, one of the few Johnson initiatives he credits.

The mechanics are what he returns to. “They just made the promise. They didn’t make the tax,” he said. The state assigned the liability and left the city to find the money. Chicago got no vote, and by his account, learned the full scope only days after the session closed.

The city’s chief financial officer at the time, Jill Jaworski, warned in writing that the change would push the pensions toward insolvency. Berg says he was the first to publish that letter. The mayor did not fight it in public. Berg reads the silence as a symptom of the same structure. A mayor with little standing in Springfield absorbs a bill the city did not get to weigh.

There is another read of the deal. The Tier 2 benefits it raised had drifted below the federal Social Security “safe harbor,” the rule that a public pension must pay at least as much as Social Security would. Falling short risked forcing Chicago to enroll those workers in Social Security or cover the gap through lawsuits, an exposure that the nonpartisan Center for Tax and Budget Accountability estimated at over $800 million a year. Roosevelt University’s Ralph Martire, who directs it, told WTTW the law fixes a real structural flaw, while faulting how it was paid for. Berg’s quarrel is with that second part, the promise without the money.

A release valve

Other cities have an exit from a bill like that. Chicago does not. “Detroit today has a better credit rating than the city of Chicago,” Berg said, and Detroit is a decade past bankruptcy. Chicago is the only city among the fifteen largest that cannot take its debts to a bankruptcy judge.

He calls Chapter 9 a last resort and wants a framework for distressed cities in place before it. An early-warning system on municipal finances. State oversight when a city runs past its means. An emergency manager who can reach a judge only at the very end. Harvey, the south-suburban city that cannot collect enough property tax to cover its debts, is his warning case.

The authority matters even when unused, he argues, because it rewrites the conversation with creditors and unions. “We can either negotiate in good faith right now,” he said, describing the leverage, “or this can go to a judge, and then it’s out of our hands.” He points to the parking meter deal as the price of having no such card to play.

The case against the tax

Berg’s tax politics start with population. “Our biggest problem as a state is three words,” he said. “People, people, people.” Illinois lost roughly a million residents over the past decade, and by his reading, the highest earners leave fastest, two out for every one in.

That is the frame for his objection to the proposed 3 percent surtax on income above $1 million. He is careful about who he is defending. “I’m not asking people to shed a tear for a pinstripe-suit, Rolex-wearing millionaire,” he said. His worry is the roughly 22,000 pass-through businesses that file at that line, the tradespeople and small operators he credits with most of the state’s new jobs, and the tax base that leaves with them. He points to Massachusetts, the one state to run a comparable surcharge. “The entire pie of the income in Massachusetts shrunk,” he said.

That read is contested, the migration piece most of all. Cornell sociologist Cristobal Young, working with two US Treasury economists, tracked every million-dollar tax return in the country over thirteen years for a study in the American Sociological Review. The rich, they found, change states at 2.4 percent a year, compared with 2.9 percent for everyone else. Tax flight runs only at the margins. The Illinois Economic Policy Institute reached a parallel result in 2026, finding that states with millionaires’ taxes grew about as fast as those without, and that a 3 percent version could raise more than $4 billion a year for schools or property tax relief. Illinois voters backed the idea in a 2024 advisory referendum, roughly 60 percent in favor. GrayStak holds no position.

Where he draws the line

On the state’s investment exclusion lists, Berg draws a line between the money a government spends and the money it owes its retirees."The Illinois Investment Policy Board keeps a set of those lists, built one cause at a time. Companies that boycott Israel. Firms that house migrant children. Businesses tied to Iran and Russia. Every state pension fund has to divest from the names on them and stay clear, and much of that territory already overlaps with federal sanctions. I asked whether a fiduciary duty, applied evenly, cuts against every screen on the list, whatever the cause.

He said it is not an issue he has worked on closely, then split the question. A state can invest by its values, the way a university weighs its endowment, and he recalled the campus fights over how endowments should be run. “You can make values-based decisions on how you want to invest,” he said. “What I don’t like is when people think there’s no trade-offs to that.”

The pension is where he holds the line. "If I'm personally responsible for managing the money of Illinois teachers' pension funds, and I need this money to exist or else someone's not getting their retirement check," he said, "my operating principle would be, you have to maximize the returns. That is the single thing you should be focused on." Political screens, whatever the cause, are "a Pandora's box" that reduces returns by necessity. Values-based choices he keeps to the operating budget, the programs a government chooses to fund.

He pointed to a case. Former Chicago City Treasurer Melissa Conyears-Ervin moved to halt the city's purchases of US Treasuries, citing the city's ability to earn the same returns elsewhere. Berg's answer was that Treasuries are the safest and most liquid asset there is, and a global benchmark. "If you're going to counter the benchmark, you need a good benchmark to counter." Pressed on what replaces it, he said no answer comes back. "China doesn't exclude the US Treasury."

Applied across the board, his answer holds for every list, regardless of the target. A political screen on pension money is a political screen, and by his principle, it works against the funds it is meant to protect.

Show your work

Berg likes the ideas grouped under “abundance,” which he reads as a catch-all for sustainable growth, and holds the label itself at some distance. His caution is with how the word gets used in a campaign. Every challenger will promise to grow the city, he said, because growth lets them avoid having to name a tax hike or a cut. “People should ask for specifics,” he said. “What do you mean by growth? What levers will you actually pull?”

His own answers start with certainty. A business plans around what it can see, and Chicago gives it little to see. “Imagine plopping down a hundred-million-dollar investment on the city of Chicago when you have no idea what it looks like ten years from now,” he said. Budget and tax certainty that lets an investor project a decade out is his first lever. Housing supply is the second. He credits the current administration with some progress on building, says it is not enough, and puts a yes-in-my-backyard stance in the column of things that would help.

Subtraction

The waiting-for-Superman reflex, Berg said, has a twin in public safety. Every flashpoint produces a call for a new office. “The political muscle, similar to this waiting-for-Superman muscle, is that we need to create another new body,” he said. Chicago already runs around eight with some oversight of policing.

He faults the city for looking inward. On the teen “takeovers” that have flared downtown for more than a year, he points to Washington, where the mayor and council passed targeted curfew zones with advance notice and services attached. “They tried it out last year,” he said. “Zero teen trends happened” before the measure lapsed and the problem returned.

His fix is consolidation. He cites two recent Matrix consulting reports, which he calls the largest review of Chicago policing since the study that produced the consent decree after Laquan McDonald’s murder, and argues the city cannot act on them while it keeps standing up new agencies. Los Angeles and its police commission are his model. He notes that the CARE mental-health response is “floundering,” in the Tribune’s words, and that the mayor’s office took down its public dashboard. Chicago police data show homicides up about 8 percent from a year earlier, a real uptick that sits on top of 2025, the city’s lowest homicide year in six decades.

What comes next

Berg wants Chicagoans to lift their heads toward other cities for solutions and to press the 2027 field on what they will leave behind. He and I plan to talk again in the fall, closer to February. His test for the candidates comes down to one question.

“What things can I do as mayor today to structurally strengthen the city, so that it’s stronger no matter who is the mayor?”

Christopher Sweat is an analyst working across finance, technology, and politics and the co-founder and CEO of GrayStak, a media and political risk company covering social and political dynamics and institutional politics at the state, local, and federal levels. He created GrayStak’s Domestic Political Volatility Index (DPVI), which measures political escalation ahead of media consensus. Austin Berg is executive director of the Chicago Policy Center. Quotes are lightly condensed from the recorded conversation for clarity. The full video interview is above. GrayStak holds no position.

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