CHICAGO — For the past 25 years, Rahm Emanuel has been involved in political trench warfare ranging from NAFTA to the 2006 Democratic House takeover to the Affordable Care Act.

Emanuel’s bid for a third term as Chicago mayor might be the toughest challenge he’s ever faced.


A slew of credentialed candidates have lined up to oust him from City Hall, and they’re engaging in an almost daily assault on Emanuel’s character and mayoralty. He’s been cast as a bully who has raised taxes, closed schools in poor neighborhoods and driven minorities out of the city.

This is all for an election that’s still nearly a year away.

Rhetoric aside, the breadth and depth of the non-partisan field is unlike anything Chicago has seen in decades, or perhaps ever, says longtime Chicago campaign strategist Don Rose.

“I would say we’ve not had as many potentially good candidates and well-known candidates as now,” Rose said. “He’s perceived as vulnerable. He is a guy who has never been personally popular. Then he faces a number of issues … the presumed big cover-up of Laquan McDonald. He faces a lot of opposition or anger still about all of the tax increases.”

Some of his opponents know Emanuel all too well. The mayor, in fact, fired two of them: former Chicago Police Superintendent Garry McCarthy and former school principal Troy LaRaviere. Then there is former CEO of Chicago Public Schools and former gubernatorial candidate Paul Vallas, Cook County Clerk Dorothy Brown and millionaire businessman Willie Wilson.

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Wilson has donated $100,000 to his own campaign, which by law removes state-imposed limits on campaign contributions in the race. That opens the door for any Emanuel enemy — and he has many — to give unlimited amounts of cash to any candidate they choose.

To date, eight people (and counting) have either filed or are likely to announce soon that they will file to challenge Emanuel in his 2019 reelection campaign. One has already purchased TV ad time. Still more are considering running — among them, activist Cook County Commissioner Bridget Gainer and progressive Alderman Scott Waguespack.

Emanuel’s campaign has already come out fighting, likening the competition to an “improv show” rather than serious opposition. That was after Brown tossed in her name, formally declaring a run on Sunday, despite being under federal investigation for hiring practices in her administration. Activist Ja’mal Green and Neal Sales-Griffin, a 30-year-old tech entrepreneur, also just announced their candidacies.

“While the political improv show continues to audition more cast members, the mayor is focused on improving schools, making streets safer and continuing to bring more jobs to every Chicago neighborhood,” Emanuel campaign spokesman Pete Giangreco said.

The still-lingering controversy over Emanuel’s handling of the 2014 police shooting of 17-year-old Laquan McDonald, which exposed deep racial divisions still plaguing the city, represents perhaps the mayor’s greatest vulnerability.

His office fought the release of a police video showing Chicago police Officer Jason Van Dyke fatally shooting McDonald, who appeared to be walking away from police when he was killed. A judge forced the city to make the video public in 2015, setting off weeks of protests. Van Dyke, who said he feared for his life, was charged with first-degree murder, and later, three officers were charged with conspiring to protect Van Dyke, including by lying on police reports. Van Dyke's trial is expected to begin this summer.

Emanuel worked through those dark days, when protesters carried caskets around City Hall and accused the mayor of hiding the video from the public to ensure his reelection earlier that year. Activists shut down Black Friday shopping on the Magnificent Mile, the city’s ritziest shopping district.

As the scandal consumed the Emanuel administration in late 2015, with calls for wholesale changes within the police department and even for Emanuel’s resignation, the mayor fired McCarthy.

The police superintendent didn’t go quietly: McCarthy accused Emanuel of trying to save his own political hide by throwing him under the bus. Violence shot up drastically in the wake of the McDonald shooting — a rise blamed both on officers backing off of dangerous stops for fear they’d be videotaped and community distrust of police as a barrier to solving crimes.

McCarthy denies that he’s challenging the ex-boss to settle a score.

“He’s a bully, and people are afraid of him. I can’t stand by and watch it,” McCarthy told POLITICO. “He would holler and scream and rant and rave. I sat in meetings where I literally saw staff people whose hands were shivering when they were picking up their water. That’s his style. He bullies people.”

Sales-Griffin said McDonald’s death was a personal “trigger point.”

“No one has forgotten about that. It’s tipped the scales to a larger problem in Chicago that we’ve always known about,” Sales-Griffin said. “When I talk about Chicago, the reaction from so many people is: 'Is it safe there? Is it OK for me to visit?' It breaks my heart to hear that. I feel personally obligated to step up and serve. Chicago is not OK. We all know it.”

While the raging violence that peaked in 2016 is starting to ramp down statistically, shootings and murders in Chicago still outpace those in other large cities, and some minority neighborhoods are still plagued with violent crime.

One of Emanuel’s own appointees, former federal prosecutor Lori Lightfoot — whom the mayor appointed to head the Chicago Police Board in 2015 — says a pervasive fear of violence has driven residents out of the city.

Lightfoot, a one-time finalist for U.S. attorney in Chicago, said she’s still weighing her own candidacy. The level of anger Emanuel faces in the African-American community is “immense,” she said.

“It’s everywhere. It’s not just young African-American men,” Lightfoot said. “Initially it was startling. It’s frankly so consistent that it’s pretty profound.”

It’s not just distrust in police and in government, she said, but frustration over persistent violence.

“I can’t figure out why there’s no sense of urgency around that,” said Lightfoot, who chaired the task force on police accountability that held public hearings to propose police reforms in the wake of the McDonald shooting. “If people don’t feel safe, nothing else matters.”

The problems vexing Emanuel go well beyond the McDonald case.

He faces the wrath of the powerful Chicago Teachers Union due to his first-term closings of 50 schools in minority communities. At the same time, homeowners face property tax increases and local fee hikes.

“He can’t talk about his successes in crime, taxes or the education system. … He makes decisions based on his own politics,” said McCarthy. “There’s shootings on Michigan Avenue. There’s bullets hitting Northwestern Hospital. … Explain to a woman who got knocked off a bike in Lincoln Park that it’s safer.”

McCarthy points to the much publicized case of a police commander who was killed in February while chasing a suspect downtown. “You wanna talk about the worst example? How about the Paul Bauer incident? A four-time convicted felon committed a murder outside of Rahm Emanuel’s window,” he said.

Emanuel said he’s had to take difficult steps, like pushing through tax hikes, after inheriting a financial mess rooted in skipped pension payments under his predecessor, Richard M. Daley.

As a result, the city’s financial picture has improved under Emanuel. Tourism has broken records under the mayor, as has the number of company headquarters relocating to the city. Even as opponents complain Chicago is a city where the 1 percent live lavishly while the neighborhoods are ignored, the mayor has touted investments in minority communities, and technological boosts to policing, which has driven down shootings in Englewood, long the city’s most violent neighborhood.

Emanuel will begin the race as the favorite, even if he’s forced into a runoff election by failing to win 50 percent of the vote plus one.

He has nearly $4 million sitting in his campaign account after depositing, on Friday, $1.7 million. That’s roughly 40 times more than Wilson, who has $100,000, and McCarthy, who’s at $91,000.

In his 2015 reelection bid, Emanuel overwhelmingly won the black vote in the runoff against Jesus “Chuy” Garcia, a Latino progressive backed by Bernie Sanders. Emanuel continues to hold an invaluable trump card in his back pocket: the support of his longtime friend and former boss, former President Barack Obama, whom he served as chief of staff before returning to Chicago in 2011 to run for mayor.

“To beat Rahm, you need a movement candidate from the left who can bring outsiders together,” said Alderman Ameya Pawar, a one-time Democratic gubernatorial candidate. “And I don’t see one out there.”