The Chicago press corps have gathered around a lectern. The city is in crisis. Schools are closed. Garbage is piling up. Government workers are striking. Businesses are fleeing. As cameras flash, the mayor of Chicago, flanked by the governor, makes a chilling announcement: “We’re flat broke.” Unless Congress steps in, he says, the state and the city will default.

This scene, pulled from Yale Prof. David Schleicher’s 2023 book, In A Bad State, which chronicles the history of federal responses to state and local budget crises, is hypothetical. But after years of rampant corruption and chronic mismanagement, Chicago is facing a confluence of crises eerily similar to the one laid out in Schleicher’s book. Once America’s most vibrant city, Chicago has been hobbled by its own leaders. The question now facing Chicago — and so many deep-blue cities that, for too long, have pursued a similar path — is whether it can be fixed, and, if so, how?

At the end of the 19th century, Chicago was not just the fastest growing city in Illinois, or the Midwest. Or even America. It was the fastest growing city in the history of the world. As it underwent a period of explosive growth, rising from 300,000 residents in 1870 to more than 1.7 million in 1900, a modern metropolis was born. Historian William Cronon coined it “Nature’s Metropolis,” connecting the rural landscapes of the American West with urban industrial markets. Chicago-born innovations like the skyscraper, refrigerated railcars, the mail-order industry and futures contracts fundamentally transformed American life.

The city’s dynamism inspired the nation. “See that cloud? That’s Chicago,” says a train passenger to Rose Dutcher, a Wisconsin farm girl traveling to the city for the first time in the 1895 novel, Rose of Dutcher’s Coolly. Emblematic of America’s view of the thriving midwestern city, this sense of awe wasn’t confined to the realm of fiction.

When the father of American architecture, Louis Sullivan, arrived just two years after the 1871 Great Chicago Fire, he was awe-struck by the Chicago skyline that he saw as a triumph of “the crudest, rawest most savagely ambitious dreamers and would-be doers in the world.” The city was “all magnificent and wild: A crude extravaganza: An intoxicating rawness: A sense of big things to be done.” Mark Twain wrote several years later in 1883, “It is hopeless for the occasional visitor to try to keep up with Chicago — she outgrows his prophecies faster than he can make them.”

This vitality is a foreign concept to many Chicagoans today. They are choking under an acrid cloud of a different sort. Poor decision-making stretched over decades, and the backward governance structure that produced those decisions, have pushed the city to the brink. And now a far-left mayor and his corrupt political machine threatens to push it over.

In the wake of the destruction caused by the Great Chicago Fire in 1871, decades of dynamism and growth followed. While Chicago’s far-left mayor, Brandon Johnson, isn’t literally burning down buildings, there’s little doubt that Johnson’s administration is a raging political dumpster fire that threatens to engulf the city. Ironically, though, it’s this conflagration that might create a generational opportunity for the kind of lasting change Chicago so desperately needs.

Though Chicago is the nation’s third-largest city, when it comes to overlapping crises across public safety, municipal finances, city corruption and (most ominously) population, the scale of Chicago’s problems dwarfs that of its peers. Once America’s fastest-growing city, Chicago is now the slowest-growing major city in the U.S. since 2000, having lost 1 million residents since peaking at 3.6 million in the 1950s. Its population now hovers around 1920s levels.

Nowhere is this more evident than in the city’s schools, one-third of which are less than half full. Frederick Douglass Academy High School on Chicago’s West Side was built to hold more than 900 students. Last year, it served just 35 students, nearly two-thirds of whom were chronically absent. Despite this, the school still employs 23 full-time staff members and spends more than $68,000 per student annually.

The city’s finances are in a similar state of crisis. For decades, Chicago politicians cut deals with government unions to boost pension benefits far beyond their willingness to hike taxes to fund those benefits. Those same leaders used money meant for pension contributions to juice pay raises for government workers and fund pet projects. Chicago now holds more pension debt than all but seven American states. Over 80% of Chicago’s property tax levy goes to pensions. And of the overall city budget, pensions and debt service eat 40 cents of every dollar — a far higher share than any other big city in the country. In order to plug annual budget gaps, past administrations have taken to selling off city assets like the parking meters. Billions of dollars in federal aid during the COVID-19 pandemic allowed the city to avoid confronting its debt and inflate spending even further, with the city’s total budget ballooning to $16.6 billion in 2024 compared with $10.7 billion in 2019. The expiration of federal aid has blown a billion-dollar hole in next year’s budget.

Safer streets would go a long way toward reversing Chicago’s population decline and growing the tax base. But violent crime resists city control. In a typical year, Chicago is home to more homicides than Los Angeles and New York combined. In 2023, the number of violent crimes in Chicago grew to its highest level in a decade, but just 10.8% of violent crimes resulted in an arrest, nearly half the rate in 2013.

Paramount to fixing Chicago’s violent crime problem is rebuilding trust in police. However, rather than focus on delivering high-quality, constitutional community policing, city leaders have made police department governance, already in a poor state, even worse. The 2014 murder of Laquan McDonald — a black teenager who was shot 16 times by a Chicago police officer — was a defining moment in exposing systemic issues within the Chicago Police Department. Video evidence contradicted initial police reports, leading to Officer Jason Van Dyke’s conviction for first-degree murder and sparking national outrage. This incident resulted in a federal consent decree in 2019 mandating sweeping reforms to improve accountability, transparency, and training within the department.

Yet, more than five years later, the Chicago Police Department has met just 6% of the court order’s requirements. Instead of focusing on these practical reforms, leaders created a Frankenstein’s monster of overlapping, politicized police oversight bodies, which frequently contradict one another. Meanwhile, Cook County State’s Attorney Kim Foxx has faced criticism for dropping felony cases at a dramatically higher rate than her predecessor.

Any diagnosis of Chicago’s problems would be incomplete without discussing corruption. The unofficial motto of Chicago politics, coined by iconic local columnist Mike Royko, is Ubi est mea?, which translates to, “Where's mine?” While falling short of the 40,000-man strong patronage army of Mayor Richard J. Daley in the 1960s, rampant corruption still emanates from Chicago’s governance structure, which gives the 50 aldermen near-despotic control over the happenings in their wards. Since the 1970s, over 40 aldermen have been imprisoned, including Ed Burke, Chicago’s longest-serving alderman and former chair of the powerful Finance Committee, who is currently serving federal prison time for shaking down the owner of a Burger King in his ward.

Though it might be hard to believe, things are getting worse. In 2023, the city elected Brandon Johnson, a former organizer and lobbyist for the Chicago Teachers Union who defeated former Chicago Public Schools CEO Paul Vallas by fewer than 27,000 votes — the smallest margin for a winning mayor in city history. If anything, Johnson’s rampage of misguided reform is an object lesson in demonstrating what happens when a far-left activist controls the levers of power in a major American city. It’s not pretty.

Over the last 18 months, Johnson’s administration has attempted to build a migrant camp on toxic land, hired four top staffers who support abolishing the police, ousted all seven members of the Chicago school board after they refused to issue a $300 million high-interest loan, appointed a 9/11 conspiracy theorist as the new school board president, demanded (and failed to secure) a taxpayer-funded stadium for the Chicago Bears, attempted (and failed) to install a socialist alderman as chair of the city’s powerful Zoning Committee, canceled the city’s gunshot detection system over the objections of black and latino aldermen, and broke his promise to not hike property taxes.

Johnson’s mayoral victory, itself governed by the same logic of power and corruption that runs the city, was the culmination of a decade-long rise — and political radicalization — of the most powerful teachers union in America. The Chicago Teachers Union (CTU) is not only Johnson’s former employer, but also his largest campaign funder and supplier of political muscle in City Hall and Springfield. It’s also the single largest spender on Chicago politics. Though its $30 million budget is funded by teacher dues, the CTU spends just 17 cents of every dollar on teacher representation. The rest goes to administration, politics and other leadership priorities.

As Bill Maher noted, this is the union that claimed efforts to reopen schools during the COVID-19 pandemic were “rooted in sexism, racism and misogyny.” Infamously, CTU President Stacy Davis Gates fought to kill the state’s only school choice program for thousands of low-income children — while sending her own child to a private school. With Johnson in the mayor’s office, the CTU is effectively seated on both sides of the bargaining table in negotiations over their new contract with Chicago Public Schools.

If Chicago’s old mayors built a tower of problems, Johnson may be remembered as the stumbling powerbroker who knocked over the edifice, exposing it for the wreck it really is. His failures have invigorated unprecedented opposition to a sitting Chicago mayor, and appetite for structural reform that the city desperately needs. Residents are seeing this play out through the emergence of a new, potentially gamechanging, political dynamic.

Earlier this year Chicago became the first big city in the nation to vote down a real estate transfer tax hike. Marketed as “Bring Chicago Home,” it would have tripled or quadrupled the transfer tax on all property sales over $1 million. In a stunning defeat for Johnson and CTU, more than 52% of Chicago voters voted down the measure — a major reversal from 2021, when 71% of Chicago voters approved a statewide progressive income tax referendum. In part due to the failure of Bring Chicago Home, outgoing Cook County State’s Attorney Kim Foxx failed to elect her preferred replacement in the Democratic primary this year. A moderate Democrat, Eileen O’Neal Burke, will become the new Cook County State’s Attorney in January.

This has emboldened the City Council, historically a rubber-stamp body, to bring meaningful opposition on key appointments, major policy decisions, and the budget. For the first time in more than 50 years, the Council took a unanimous 50-0 “no” vote in November, rejecting Johnson’s proposed $300 million property tax hike.

With all this unfolding, key elements of the Chicago party machine are shedding support. Johnson’s own favorability rating among Chicago voters has dropped to just 14%, the lowest of any mayor in history. The CTU, which historically enjoys between 60-70% support, has seen its approval rating similarly plummet, with 28% of city voters saying they see it favorably.

As a result, momentum is building for structural changes to city government. One key finding from our book on Chicago governance was that of the 15 largest cities in the U.S., only Chicago lacks a city charter. In absence of the checks and balances provided by this basic governing document, chaos and recklessness abound. But in the last year alone, faith leaders, state lawmakers, City Council members, and prominent civic institutions have openly backed a voter-approved city charter for Chicago, marking the first time in over a century that this critical reform has been part of the conversation.

In the meantime, Chicago’s fall — and possible rise — should be seen as a lesson for the nation. Of course, the Johnson administration puts into stark relief why far-left leaders who swoop into office with promises of big changes are more likely to be an anti-solution to the problems plaguing big cities. But the city also teaches us something about the importance of city-charter design. Though generally under-discussed, charters can decide everything from when elections are held, to who is elected, and when those elected officials must ask voters for permission. Effective charters provide clear rules of the road that all must obey. Not only do those rules prevent radicals from driving your city into a ditch. They also scaffold vibrant civic cultures, which immunize against the sort of managed decline from the political class that has so harmed Chicago.

Despite everything, Chicago is still an American titan: Nowhere else in the country can claim such cheap access to the richness of life that a big city provides. But it is the worst governed American city. As a result, it is an outlier with severe problems. Those problems are man-made, which means the solutions are, too. This may be Chicago’s turning point — a moment to rebuild its foundations. Not just in steel and cement but in accountability, transparency, and a government that serves its people. If the city’s past is any indication, it’s when Chicago is on the ropes that it finds the will to rise again.

—Austin Berg