Rahm Emanuel became mayor of Chicago in 2011, just as the city was coming out of a lost decade. The Chicagoland region had lost jobs, and the city was staggering under the weight of civic debacles, ranging from the 75-year lease of its parking-meter system to a humiliating rejection of its bid to host the 2016 Olympics. Today, after seven years of Emanuel’s leadership, the Loop enjoys record employment, vast tracts of the city are booming, the tech sector is gaining momentum, a sparkling new downtown river walk is drawing huge crowds, and the city can justly boast that its transit system is not suffering from the critical breakdowns slamming New York and Washington. The mayor surely wants this significant turnaround to mark his legacy.

But while Chicago is better in many ways for his time in the mayor’s office, Emanuel largely failed at grappling with the city’s biggest problems: finances and violent crime. And he couldn’t bring Chicago to parity with the elite global cities on the coasts.

Emanuel inherited the city’s grievous financial crisis, created by his predecessor Richard M. Daley. The city was largely in the dark about the woeful state of its ledgers until a Crain’s Chicago Business report appeared in 2010, followed soon after by investigative reporting that revealed deep-seated problems: severely underfunded pensions, high levels of bonded debt, constant refinancing to extend payments (termed “scoop and toss”), and the use of debt to pay operational expenses, including millions of dollars in settlements for police misconduct.

After eight years, Chicago is only beginning to address these challenges. Emanuel first attempted to negotiate a solution with public-sector unions—the right move to make, though it proved futile in the face of Illinois Supreme Court rulings that effectively invalidated any form of pension reform. But while pursuing these efforts, Emanuel neglected to increase funding for the pension system, a costly decision during one of the all-time-great bull markets.

Now, at the end of Emanuel’s second term, Chicago faces the prospect of many years of tax increases to close the pension-funding gap, with city contributions to the system almost set to double by 2023. What mayor wants to preside over years of tax increases that produce no public benefit, going only to pay for yesterday’s mistakes? This looming future perhaps helps explain Emanuel’s decision to step down. The mayor recently floated a proposal for a pension-obligation bond, generally a move suggesting desperation.

Emanuel also never got a handle on crime, as Chicago became a national byword for homicide. In 2017, the city continued to rack up more than double the combined number of murders in Los Angeles and New York, both larger cities than Chicago. The city made national news for multiple weekends this past summer, with stunning numbers of shootings—such as the first weekend in August, in which 66 people were shot, 12 fatally. The city has also seen a wave of car-jackings, which have plagued even the most prosperous neighborhoods. Chicago’s crime story is complex, but public safety is the most important job of any mayor, and Emanuel clearly failed to keep Chicago safe. The behavior of some Chicago locals in trying to explain away the killing—such as comparing the city’s murder rate with that of Memphis and Detroit, two cities that Chicagoans would never otherwise want to be lumped in with—is a civic disgrace.

Emanuel’s successes are also less impressive than they might first appear. Chicago’s economic turnaround was part of a national boom. Other American cities have been rallying economically, too, and often at a faster rate. Tech is growing all over, and Chicago hasn’t cracked the elite club in venture-capital investing, remaining significantly behind the big four coastal centers (the Bay Area, Los Angeles, New York, and Boston). And unlike the other largest American cities, Chicago continues to see its population fall, as blacks flee in droves and Mexican immigration dries up.

Emanuel brought formidable skills to city hall, but they were not necessarily the ones that Chicago needed. The mayor is a hardened political streetfighter, and that helped him in some aspects of his job. He pursued his goals with relentless ferocity. His ability to get out-of-town CEOs on the phone at will—a rarity among mayors—helped him bag several major job announcements early on, which put wind in the city’s sails at a time when Chicago badly needed a boost. But Emanuel’s lack of strategic and operational skills hobbled his ability to respond to structural and systemic problems. And his Washington-style approach to spin doesn’t work at the urban level, because residents have firsthand knowledge of how their neighborhoods are doing and won’t fall for media massaging. That top-down effort at controlling the narrative reached its nadir just before the last election, when the city sat on a video of a Chicago cop shooting and killing 17-year-old Laquan McDonald. The officer is only now headed to trial, and the verdict, whatever it may be, will cast a shadow on the 2019 election.

Taking a job as a big-city mayor, especially of Chicago, is not exactly a strategic career move; Emanuel, a well-connected power player who served in two presidential administrations, deserves credit for his civic ambition. His departure is of enormous consequence for the city. No obvious successor is in sight, and the race looks wide open. In choosing a new mayor, Chicago will have an opportunity to break free of its clout-driven, “big daddy” style of governance—an unwelcome prospect for the city’s civic and business elite, who fear more than anything a return of the chaos that the city experienced in the 13-year interregnum between the two mayors Daley, père et fils. Some level of chaos may indeed come, and it may even be healthy. Chicago needs to create new and more open political structures that can produce better outcomes and a healthier civic culture; an electoral shakeup could help start that process.

Chicago Mayor Rahm Emanuel (Photo: Joshua Lott/Getty Images)