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Why Is It So Hard to Run Chicago?

Mayor Brandon Johnson has struggled to accomplish big things, and his predecessor had an even harder time. History suggests some building blocks of mayoral success.

Chicago Mayor Brandon Johnson
Chicago Mayor Brandon Johnson speaks at a news conference on March 20, a day after the election in which citizens voted down his $800 million plan to aid the city’s homeless people. (Chris Sweda/Chicago Tribune/TNS)
It’s been just a year since Brandon Johnson took office as the 57th mayor of Chicago, offering a dramatic vision and a potpourri of promises. He made frequent references to “the soul of Chicago” and declared that “a brand-new Chicago is in front of us. I can’t wait to continue to lead this city” toward a rebirth of its soul. “I campaigned on change,” he told his inaugural audience, “you voted for change and I plan to deliver change.”

In the months since then, Johnson has had some modest accomplishments to talk about. He raised the minimum wage for tipped employees. He opened two new mental health clinics. He began making moves for a return to the neighborhood school network his predecessors had disdained or ignored.

But it’s a different event that is overshadowing his mayoralty and may define him for years to come: his embarrassing failure to deliver on “Bring Chicago Home,” a plan to raise $800 million in tax revenue to create a massive program of aid for the city’s homeless people. The plan was defeated by 21,000 votes in a citywide referendum this past March, blocked by opposition from the city’s real estate establishment and most of Chicago’s business community. Johnson says he will try again, but “Bring Chicago Home” appears to be down for at least the near future.

Real estate interests spent more than $600,000 on an ad campaign that featured the slogan “the city wants even more of your money” and focused on a new tax on property transfers that would have brought in at least $100 million. They described the $800 million in proposed spending as a slush fund for Johnson’s supporters, especially the teachers’ union, for which he once worked.

Johnson’s tax would have targeted the wealthy, but his initiative went down to defeat in nearly all of the city’s working-class and middle-class neighborhoods. A caucus of progressive City Council members, most of whom had backed Johnson’s scheme, conceded after the defeat that “voters had real questions about whether or not they could trust the government to spend the money the right way.” In one poll taken after the vote, Johnson’s favorability rating in the city stood at 27.1 percent.

The details of Johnson’s plan were new, but the idea wasn’t. His predecessor, Lori Lightfoot, had used the phrase “Bring Chicago Home” in voicing her commitments to a dramatically improved Chicago. “For years, they’ve said Chicago ain’t ready for reform,” Lightfoot told her own inaugural audience. “Well, get ready, because reform is here.”

Only it wasn’t, at least not her version. Lightfoot never even attempted anything like “Bring Chicago Home.” As her four-year term proceeded, she fought almost incessantly with virtually every important constituency in the city, and by the end of the term she was so unpopular that she finished a distant third in the primary, failing to make the runoff.

WHY DID JOHNSON AND LIGHTFOOT FAIL SO BADLY at forging a consensus behind what they wanted to do? And what are the building blocks of mayoral success, in Chicago or in any other large American city? Those are questions that suggest a dip into a few decades of mayoral history.

The simplest answer is that the more a new mayor promises to achieve, the more he or she is likely to be disappointed. Lightfoot and Johnson vowed in essence to create a new Chicago, but remaking a city is not something any incoming mayor is likely to deliver on, especially in a single four-year term.

It’s an old truism in Chicago politics that the city gets two kinds of mayors: reformers and builders. The reformers promise extravagantly and run into obstacles at almost every turn; the builders go easy on promises and concentrate on physical progress. Often this has embodied a greater or lesser degree of corruption, not necessarily involving the mayor personally but allowing job-dependent graft at lower levels of the political system.
Jane Byrne and Richard J. Daley
Jane Byrne, a Chicago city commissioner and future mayor, shares a podium in 1973 with her political mentor, then-Mayor Richard J. Daley.
(Chicago Tribune/TNS)

Back in the Depression years, Mayor Edward Kelly, who served from 1933 to 1947, presided over a notoriously corrupt city; he also presided over construction of an extensive subway system that remains functional almost a century later. Richard J. Daley (1955-76) was personally clean but tolerated graft in the building process that helped him revive downtown after decades of stagnation and created a residential boom near the urban center that became the engine of the city’s late-century prosperity. His son, Richard M. Daley (1989-2011), didn’t talk much about reform but generated the physical changes, epitomized by the restoration of the Chicago River and the wildly popular Millennium Park, that made Chicago a thriving global city for virtually all of his tenure.

By contrast, the two most determined change agents of modern times, Martin Kennelly (1947-55) and Jane Byrne (1979-83), were the least adept at bringing change about. The more successful Harold Washington (1983-87) has sometimes been described as a reformer, but this isn’t entirely right. Washington’s campaign mantra (“It’s Our Turn”) reflected a desire to bring the city’s African American community the share of conventional political clout that they had been denied through Chicago’s long history.

PERHAPS THE MOST IMPORTANT POLITICAL MOVE any Chicago mayor has to make is to reach an accommodation with the 50 members of the City Council. Chicago is often described as a strong-mayor city — and in many ways it is — but an obstreperous council can cause enormous problems for an ambitious mayor of any stripe.

In the early part of the 20th century, the council members were derided in the press as “gray wolves” — so dubbed by muckraker Lincoln Steffens “for the color of their hair and the rapacious cunning and greed of their natures” — and they ran their wards as personal fiefdoms, regardless of whether the mayor approved or not. Mayor Anton Cermak managed to tame the wolves with a newly built machine for two years before his death in a failed assassination attempt on Franklin D. Roosevelt in 1933. Mayoral control lived on, with periodic interruptions, for the rest of the century.

Richard J. Daley used the levers of patronage to keep the council under his thumb; he also removed some of the council’s most egregious prerogatives, such as the power to extort bribes for homeowners’ driveway permits. Much of the patronage network was gone by the time his son became mayor, but Richard M. Daley got most of what he wanted from the council, in large part because he had appointed a large proportion of its members to vacant seats.

BUT MAYORS WHO FAILED TO ABSORB THE DALEY LESSONS have suffered at council hands. That includes the two most ambitious and yet inept reformers, Kennelly and Byrne. It also includes, in large part, Harold Washington, whose goals as the city’s first Black mayor were frustrated by a solid block of council opponents — although the council’s obstructionist behavior became so offensive that Washington was able to win a second term.

More recently, Lightfoot’s council relations were so poisonous that a second mayoral term was out of the question for her. Brandon Johnson has been more effective at dealing with the council members, but he has failed, so far at least, to build a citywide constituency large enough to enact his most fervently promised goal of a large tax increase to support programs for the homeless.

The first Mayor Daley was fond of offering some pithy advice to his political allies. “Don’t get in any fights you can’t win,” Daley used to say. “Don’t get in any fights you don’t need to win.” The mayors who have understood that have consistently been the most successful ones.

Somewhat more famously, the late Gov. Mario Cuomo of New York offered some wisdom about the nature of modern statecraft at all levels of the American political system. “You campaign in poetry,” Cuomo declared. “You govern in prose.” This is easy to grasp, but difficult to practice. A newly elected mayor of any city these days finds it hard to resist the temptation to repeat extravagant campaign promises and declare that a new day is dawning, that the city is going to change dramatically under his or her leadership. But the beginning of a new mayoral regime is the time to shift gears and start governing in prose. Brandon Johnson, unlike some of his predecessors, seems to understand that. He still has time to practice it.
Alan Ehrenhalt is a contributing editor for Governing. He served for 19 years as executive editor of Governing Magazine. He can be reached at
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