Chicago Mayor Rahm Emanuel and his wife Amy Rule attend the 2013 presidential inauguration
Chicago Mayor Rahm Emanuel with his wife, Amy Rule, at Barack Obama's second inauguration in 2013. Pool/Reuters

Campaign insiders offer clues to the reasons for Emanuel’s startling announcement that he won’t seek reelection as mayor. (Others just say “good riddance.”)

On September 7, 2010, Chicago Mayor Richard Daley—the “mayor for life”—announced he would not be seeking reelection to his 7th term in office. On Tuesday, his successor, Rahm Emanuel, made the same move. In a press conference Tuesday morning, he abruptly announced that he was throwing in the towel after his two terms were up, even though he has already raised millions in campaign funds.

“The time has come to make another tough choice,” Emanuel said at Chicago’s city hall, flanked by his wife, Amy Rule. “This has been the job of a lifetime, but it’s not the job for a lifetime.”

The announcement came as a surprise even to insiders, and raised several questions—some to do with Emanuel himself, and others with the fate of the city he oversaw during two tumultuous terms in office.

First up: So why’d he do it? And why now? Well, for one, his prospects in this mayoral race were starting to look pretty bleak. According to Tom Bowen, who served as Emanuel’s deputy campaign manager in 2011 and the director of his political action committee until 2013, there had long been signs that this election was going to be a hard one for Emanuel. After Donald Trump took the presidency and Republican Bruce Rauner won the gubernatorial seat in Illinois, Chicago seemed as if it might be ready for a change. “It’s not a great environment for any incumbent,” he said. “Voters were clearly very frustrated.”

A lot of that had to do with Emanuel himself, of course. He had been languishing in the polls—and not just because of his famously quick temper, which he had the habit of letting loose around reporters. In his two terms, he oversaw dramatic tax hikes, shuttering of mental health clinics, union strikes, public school closings, population loss, a spike in violent crime, and reports of egregious police misconduct.

“I don’t believe any single issue is the biggest driver of this decision. It took all these things coming together in a perfect storm,” said Bowen, who now runs a political consulting firm.

The shooting death of unarmed Laquan McDonald was surely a turning point, though. When a court ordered the release of the video footage of the 16 shots officer Jason Van Dyke fired into the 17-year-old, floodgates of anger in the city flung wide open. Investigations revealed how Emanuel’s administration had screwed up. Thousands of documents on police misconduct were released. Emanuel’s ratings tanked. And while he never heeded calls to resign, his opponents persisted, and grew louder. Today’s announcement, in the eyes of many Chicagoans, is a win for local criminal justice activists.

But if Emanuel had remained so stubborn on this issue of running, why make this announcement now? As Fran Spielman from the Chicago Sun-Times wrote last week, he was nearing a political deadline of sorts, as the Jason Van Dyke murder trial approached:

If Emanuel waits much longer, he will risk looking like his political future is being dictated by the outcome of the trial of Chicago police Officer Jason Van Dyke, who is charged with the murder of Laquan McDonald.

Still, despite all of these disadvantages, it was widely believed that he’d stay in the race; he may have been unpopular, but he was—and still is—extremely powerful. Former presidents Barack Obama and Bill Clinton have served as allies and advisors. He also has deep pockets: For his mayoral bid, he raised five times the amount ten of his rivals raised together. For all of these reasons, some on Twitter speculated today that he might be eyeing the 2020 presidential race after he relinquishes his mayoral duties. Whether or not that turns out to be true, he is not likely to disappear into the background.

“Obviously the guy’s got $10 million dollars in his campaign war chest, so he’s going to be a player moving forward,” said Ron Holmes, a political strategist in Chicago with ten years of experience in Illinois politics.

The race for the future of his office, meanwhile, is turning into an open rush. The already-large pool of candidates is about to get bigger, with more and more city officials expressing interest in throwing their names in the hat. Although it’s much too early to say who is likely to emerge as the frontrunner in the 2019 race, some point to Lori Lightfoot—a progressive, female candidate of color with criminal justice credentials—as a candidate with the right profile.

The bottom line is that Chicago is hungry for someone who can offer a vision for the future of the city that is clearly different from Emanuel’s, but also stands strong on its own, experts said. This candidate will need to have the infrastructure in place to organize, to rally the support of Chicago’s diverse voting blocs, and to strengthen the city from the bottom up.

“I think what voters in Chicago want is similar to what they want nationally—they want things to be better; They want their government to look like them and to reflect their values,” said Bowen. “So it’ll take someone offering a progressive vision, but a vision that’s different from what’s gotten them into that mess.”

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