As scramble for Chicago mayor begins, a grueling job with a history of larger-than-life personalities awaits

Chicago Mayor Rahm Emanuel announced this week he would not seek a third term in office.
(Stacey Wescott / Chicago Tribune )

For any Chicago politician, becoming mayor represents a lofty and rare opportunity, but the complexities of governing the nation’s third largest city — and tending to its many nagging problems — can quickly ground the victor in a grim reality.

Rahm Emanuel’s stunning decision Tuesday not to seek a third term as mayor underscored the grueling job that lies ahead for the next person who occupies the suite of offices on City Hall’s fifth floor. Even Emanuel — a hard-charging veteran who is no stranger to playing the role of political bully to force through his agenda — realized that for him, holding the job for four more years wasn’t worth another fight.

“I made a number of phone calls to tell people my decision, and everyone was surprised. Nobody ever thought the person who lives, breathes, eats, sleeps politics would ever have the courage to push the table away and say, ‘I’m done,’” Emanuel said in an interview with the Chicago Tribune hours after he made public his decision to step aside. “It was baked into the cake, and I’m taking the baking powder, baking soda, the flour and the eggs away. … Only those of us who sit in these chairs — especially the chief executive one — only they can fully appreciate the sacrifices.”

Now, a crop of well-known local players sees an opportunity to seize the moment and join the field for a Feb. 26 election, including Cook County Board President Toni Preckwinkle, state Comptroller Susana Mendoza, former U.S. Commerce Secretary William Daley and Democratic U.S. Reps. Luis V. Gutierrez and Mike Quigley. Those potential candidates and others have been furiously dialing big-dollar donors, labor bosses and community leaders in the days since Emanuel’s departure from a race that already included a dozen other challengers.


Who ultimately gets to go through the political wringer at City Hall next is up to voters, but for all the hopefuls, there are warnings to heed.

“The job of mayor has a mythic standing in our politics, and very rarely does the office come open, so it’s hard when the grail is dangling not to reach for it,” said veteran political strategist and Emanuel friend David Axelrod, who also served as a senior advisor to former President Obama.

But, he said, being Chicago’s mayor “is a relentless and monstrously complex job. You have to have the mastery of a lot of different issues, but you also have to have the ability to deal with lots of different people and constituencies. I’m sure everyone who’s thinking about it has the confidence that they can handle it, but it behooves them to think through really what the demands of the job are.”

On the horizon for Chicago’s next mayor: a rampant violent crime problem that shows little sign of relenting, a police department that will be forced into reforms by a federal judge, more than $700 million in increased pension payments that could warrant substantial tax increases, South Side and West Side neighborhoods that continue to experience population loss and a shortage of economic opportunities, and a declining citywide student population that could lead to more school closings and consolidations.


Also on the to-do list is trying to bridge the city’s long-standing racial divides at a time when they’ve been inflamed by the ongoing murder trial of white Officer Jason Van Dyke for the 2014 police shooting of black teenager Laquan McDonald.

Add to that a job that’s highly visible with around-the-clock demands even in good times, and the next mayor is staring at “perhaps the most difficult four-year mayoral term we’ve seen in recent history,” said Chicago Alderman Brendan Reilly.

“The next mayor is going to be the first person to receive phone calls about overnight shootings, homicides, a nearly daily occurrence. Never mind all the other issues, like the pension obligations that have to be met in a very aggressive fashion, and there are no easy solutions there,” Reilly said. “Whomever wins this office will probably enjoy that victory for all of 12 hours before they have to get knee-deep in it and do some really hard work.”

Having a towering persona, an influence to command the national political stage and a stamina that matches the strength and grit of Chicago’s working class long have been key attributes to winning and keeping the job of mayor.


“It’s a really, really hard job, and there’s a reason why the people who are most successful at it tend to be larger-than-life figures,” Axelrod said, before invoking Carl Sandburg’s epic poem “Chicago.” “You have to have very, very big shoulders to be the mayor of the city with big shoulders.”

Just take a look at the past — when Chicago’s mayors often were mentioned on the city’s streets by a single name. There was Hizzoner, Janey, Harold, Richie and then Rahm.

Mayor Richard J. Daley was the personification of that style of a city leader, running a vaunted political machine based on patronage that forced aspiring politicians to view him as a gatekeeper to careers from governor and senator all the way to president.

Jane Byrne brought an outspoken show-business style in her role as the city’s first female mayor, unafraid to attack a male-dominated ruling class in the city government of the late 1970s and early 1980s.


After enjoying a more sedate schedule in Congress, an effervescent Harold Washington threw himself into being mayor in the 1980s and learned to embrace its high profile along with its symbolic working-for-the-everyman ethic, particularly in the black community.

Richard M. Daley brought his iconic family surname back to City Hall, replacing his father’s hard edges with a willingness to build citywide coalitions that made him Chicago’s longest serving mayor.

And then came Emanuel, a former congressional leader and veteran tactician for two presidents who arrived with a national pedigree that he tapped often to keep Chicago at the center of the national political discourse, particularly in the era of President Trump.

Perhaps unique among political posts in Illinois, the job of Chicago mayor is one of constant scrutiny, visibility, criticism and demands. It may be viewed as a political prize, but it’s far from a plum job.


Alderman Ricardo Muñoz, who has served 25 years on the City Council, said few in Chicago know or have “what it actually takes to be mayor.”

“It’s a really tough job,” Muñoz said. “No. 1, it’s thankless and you have to have really thick skin; and No. 2, you’re expected to solve everyone’s problems.”

In addition to the “huge albatrosses” of crime, schools, neighborhood development and city finances, Muñoz said the next mayor can expect to hear complaints from all corners — and on all issues, from rats to rezoning.

Whether it’s negotiating with Fortune 500 CEOs or getting the latest weekend homicide reports, Muñoz said, there is one characteristic every Chicago mayor should have.


“To be the moral leaders of a city this size with these types of problems, you got to be stoic about it — physically, mentally and emotionally,” he said. “Your every move is going to be watched.”

South Side Alderman Roderick Sawyer knows what it takes to be mayor — his father had the job. Eugene Sawyer was mayor for 16 months in the late 1980s following Washington’s death.

When his dad took office, Sawyer was 24 years old and in law school. Up until that time, he and his father were very close, and he spent many hours along his side at City Hall while the elder Sawyer was alderman. His father became mayor after a bitter City Council feud that saw a bloc of majority white aldermen vote him into the position over then-Alderman Timothy Evans, Washington’s protege.

“He was my best friend. We were together all the time. When people saw him, they saw me,” Sawyer said of his father. “Once he became mayor, I hardly saw him. It was few and far between, and that was stressful, because we were very tight. My dad loved the position, hated the circumstances that got him there, and he was distraught about it. The noise around it, the names he was called, the things he was accused of being that he was not. It was extremely stressful on all of us.”


With Emanuel out, the field of mayoral candidates for the February election stands at a dozen. If no candidate receives more than 50% of the vote — a strong likelihood — then the top two vote-getters will square off in an April 2 runoff.

The main candidates who have declared so far: former Chicago Police Supt. Garry McCarthy, former Chicago Public Schools Chief Executive Paul Vallas, former Police Board President Lori Lightfoot, Cook County Circuit Court Clerk Dorothy Brown, millionaire businessman Willie Wilson, Chicago Principals and Administrators Assn. President Troy LaRaviere, activist Ja’Mal Green, tech entrepreneur Neal Sales-Griffin, attorney Jerry Joyce, policy consultant Amara Enyia, attorney John Kozlar and DePaul student Matthew Roney.

A number of politicos are weighing whether to jump into the field, but the biggest names remain Preckwinkle, Mendoza, Gutierrez, Quigley and Bill Daley, the 70-year-old brother and son of two former mayors.

Ruthhart and Pearson are Chicago Tribune correspondents.