He became mayor of Chicago in 2011, riding a wave of national political celebrity after serving as President Barack Obama's first chief of staff. After failing to solve persistent problems in basic functions of the city, such as law enforcement and education, he stunned Chicago on Tuesday by announcing he will not seek a third term.
"It's certainly a shock to the political system here," says Chuck Bernardini, a former alderman.
Emanuel had already drawn a dozen opponents for the election, which will be held in February. His departure from the race may draw new entrants, with the city's business community -- which had backed the incumbent strongly -- left looking for a champion.
Given less than six months remains before the election, any new candidate would have to raise money and build an organization quickly. Part of the surprise of Emanuel's announcement was due to the fact that he'd already raised more than $10 million toward his campaign.
“I’ve decided not to seek re-election,” Emanuel said in a press conference. “This has been the job of a lifetime, but it is not a job for a lifetime.” He also stated that spending more time with his family was now his priority.
Despite his stumbles and policy shortfalls, most pundits believed Emanuel was on his way to a third term. "The serious observers thought he could have won if he'd stayed in," says Bernardini.
Four years ago, Emanuel became the first Chicago mayor forced into a runoff. The complaint then was that Chicago represented a "tale of two cities," with the Loop and the North Side attracting development and jobs, while the South and West sides were mired in poverty and crime and draining population.
To a large extent, that narrative has not changed.
"Early Christmas miracle!" tweeted Republican consultant Gianno Caldwell on Tuesday. "Rahm Emmanuel not running is the best news Chicago has received all year. Now we need a mayor that gives a damn about the people -- all the city residents."
The center of the city has thrived under Emanuel. Major corporations, such as Motorola and McDonald's, have moved their headquarters out of the suburbs and into the city. But Chicago as a whole has not shared in the largesse.
"The city has lagged in recovery," says Dick Simpson, a former alderman and political scientist at the University of Illinois at Chicago. "It's only now back to the kind of development and tax base it had before the Great Recession."
Simpson, and others, say Emanuel deserves credit as a financial manager, raising taxes to bring down the city's "incredible" pension debt.
"He's paid close attention to the details of governing," says Avis LaVelle, a communications consultant who served as press secretary for Mayor Richard M. Daley, Emanuel's predecessor. "He's trying to get our financial house in order."
It's not in order yet.
Chicago's financial balance sheet may still be the worst of any major city. Despite increases in taxes and real cuts to expenses, the city ran $1 billion short last year. The pension funds, in particular, were $28 billion short at the end of last year. That represented a decrease of nearly $8 billion from 2016, but may be based on rosy assumptions about how much the city will be able to contribute in the coming years.
Already, Emanuel raised pension contributions by $800 million annually through property tax increases and other fees and taxes. Making matters more difficult, an attempt by the city and the state of Illinois to lower pension burdens by cutting promised benefits was struck down by the Illinois Supreme Court in 2014.
Emanuel's handling of crime and schools has drawn even more heated criticism than the city's fiscal mess. The murder rate in Chicago has become synonymous with urban crime, at least in political circles. It's actually come down the last two years, but Chicago remains a dangerous city. Over the first weekend in August, 63 people were shot, and 10 people were killed. Anti-violence protesters have shut down freeways as recently as Labor Day.
In a scathing report issued at the end of the Obama administration, the Justice Department found that the Chicago Police Department "engages in a pattern or practice of using force, including deadly force," in violation of the Constitution. The lengthy report described frequent police aggressions aimed overwhelmingly at black and Hispanic residents.
Emanuel was accused of suppressing the release ahead of his election in 2015 of a dash-cam video of the police shooting of Laquan McDonald, a black 17-year-old. Protesters marched for weeks, and Emanuel fired Police Superintendent Garry McCarthy, who is now a candidate for mayor. Jury selection is scheduled to start Wednesday in the trial of Jason Van Dyke, the officer involved in the shooting.
Emanuel got out into the neighborhoods more often than his critics contended, but he was not always able to convey to residents in neglected areas of the city that he had a high regard for them or was attuned to their concerns.
That came up on various matters, notably the closure of dozens of schools. Emanuel advocated for change when it came to education, noting when he ran that Chicago had shorter school days and years than any other big city. But he never fully articulated his vision of the balance between charters and traditional neighborhood schools. That led to an ongoing war over resources between advocates from those two camps, most dramatically in the 2012 teachers' strike.
"Why he opted to immediately become confrontational with the most important institution, attacking the Chicago Teachers Union, remains a bit of a mystery," says Robert Bruno, director of the labor education program at the University of Illinois at Chicago and coauthor of A Fight for the Soul of Public Education: The Story of the Chicago Teachers Strike. "It just made it impossible ultimately to make a deal without a pretty unprecedented and shocking labor walkout that went way beyond [what] he could have anticipated."
A Stanford University study released last year found that, between 2009 and 2014, standardized test scores rose in the city faster than in 96 percent of districts nationwide. "All the arrows are pointing up," Emanuel said last week.
But people have been voting with their feet. Enrollment has declined by more than 10,000 students over the past two years. (Figures are not yet available for the current term.) A district that had 438,589 students back in 2002 was down to 371,382 last fall.
This summer, the Chicago Tribune reported on sexual abuse in the schools in a series of articles, with the district failing to protect students in more than 100 cases, with educators failing to report suspected cases of abuse and employees with records of sex crimes passing background checks. The newspaper's investigation led to a report last month from a former federal prosecutor finding that there were "systemic deficiencies" in the district's handling of sexual misconduct in schools.
Problems with police, schools and inequality have all been central to the mayor's race. The leading candidates are McCarthy, the fired police superintendent; former Chicago Schools Chief Paul Vallas, and former police board president and prosecutor Lori Lightfoot. But it's likely Emanuel's announcement will draw in others.
"My guess is that we'll see some more candidates now," says Bernardini.
The vision that Daley laid out for the city and Emanuel brought to greater fruition -- for Chicago to be a node in the global economy -- has been at least partially fulfilled. But whoever wins will also inherit all the problems that Emanuel was unable to solve.
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