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 occupiesthe 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 players sees a real-time opportunity to seize the moment and join the field for the Feb. 26 election, including Cook County Board President Toni Preckwinkle, state Comptroller Susana Mendoza,former U.S. Commerce Secretary William Daley and U.S. Reps. Luis 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 adviser to former President Barack 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.”
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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 police shooting of black teenager Laquan McDonald.
Lop that on top of 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 downtown Ald. Brendan Reilly, 42nd.
“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.”
‘Very big shoulders’
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 — whenChicago’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 figurehead, 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 Donald Trump.
Perhaps unique among political posts in Illinois, the job of 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.
Ald. Ricardo Munoz, 22nd, 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,” Munoz 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, Munoz said the next mayor can expect to hear complaints from all corners — and on all issues, from rats to rezoning.
“When a water main gets replaced and one of your supporters or campaign contributors lives on the block, he or she will call you three times a day about how the Water Department hasn’t put up the right barricades,” Munoz said. “You, as mayor, will get those phone calls — and of course, you’ll send it to staff — but you’re still in the middle of it, and there is no problem too small you won’t hear about constantly. They think their problem should be your No. 1 issue.”
Whether it’s negotiating with Fortune 500 CEOs or getting the latest weekend homicide reports, Munoz 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 Ald. 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 6th Ward 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-Ald. 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.”
Sawyer, 6th, has kicked around the idea of running for mayor, but said he’d only do it if he were “called to serve,” and his family is less than thrilled by the idea.
“People have to understand it’s a tremendous sacrifice. It’s not just a job. It’s the ultimate in local public service that you can do, but it’s extremely demanding on your personal time,” he said. “When I talk to my wife and family about doing it, to be honest, they’re not that interested in that, because they like dad and Rod the husband, and we like to go out and have fun, go out to dinner and go out to the movies.
“That stuff stops if you’re mayor,” he said, adding, “It’s extremely taxing. It’s something that is risky. It can decimate a family.”
Scramble for support
With Emanuel out, the field of mayoral candidates for the February election stands at a dozen. If no candidate receives more than 50 percent 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 Superintendent Garry McCarthy, former Chicago Public Schools CEO Paul Vallas, former Police Board President Lori Lightfoot, Cook County Circuit Court Clerk Dorothy Brown, millionaire businessman Willie Wilson, Chicago principals association President Troy LaRaviere, activist Ja’Mal Green, tech entrepreneur Neal Sales-Griffin, Southwest Side 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.
All of them spent much of the week placing dozens of phone calls to corporate executives, union bosses, big-dollar donors and political consultants as they tried to gauge whether they can muster enough support to run viable campaigns, according to a dozen sources who spoke directly with the potential candidates.
The behind-the-scenes sprint seemed strongest between Preckwinkle and Mendoza, both of whom have won strong backing from the traditional Democratic establishment and organized labor in their previous campaigns.
Besides her tenure as Cook County Board president, Preckwinkle, 71, also chairs the county Democratic organization — a post she assumed after Cook County Assessor Joe Berrios’ March primary defeat. Her party post puts her in a politically advantageous early position by forcing fealty from among the city’s 50 Democratic ward committeemen.
But the county Democratic organization remains a far cry from its glory days, and many of Preckwinkle’s allies represent the old-school politicians of the past, evoking concerns from critics that she would provide a landing spot for them while failing to move the city forward.
Mendoza, 46, is Illinois’ first statewide elected Hispanic official and has shown her ability to engage in bruising political fights. She lost her first bid for the Illinois House three decades ago by 55 votes to an incumbent Democrat only to win two years later in a rematch by more than 800 votes. She left the legislature for city clerk in 2011, won re-election in 2015 and then won a special statewide election to a two-year term as comptroller against Republican Gov. Bruce Rauner’s appointed officeholder.
In the comptroller’s office, she has been an energetic and outspoken Rauner critic. Though she holds an executive office, some critics quietly question her executive experience as well as the depth of her political pedigree.
Since she’s seeking re-election to the post on Nov. 6, Mendoza must do a political dance to maintain interest in her current job while eying a potential run for mayor afterward. Preckwinkle faces a similar re-election bid on the November ballot, but, unlike Mendoza, faces no opponent. The petition filing deadline for getting on the city ballot is 20 days later.
Mendoza and Preckwinkle each have been reaching out to organized labor, a source of substantial political support in the past. As for Mendoza, “she’s not too concerned about who else gets in the race,” said one high-ranking official of a politically active union who was not authorized to speak publicly about the race. “Susana thinks she’d be the best candidate in the race, no matter who gets in.”
After a Chicago Federation of Labor meeting Thursday, most union representatives agreed to hold off on quickly endorsing anyone, and there is a push to have organized labor unite behind a single candidate.
Insiders handicap Mendoza as a particular favorite among the building trades unions while Preckwinkle is closely aligned with public employee and services unions. Service International Employees Union Local 1 is conducting a poll for Preckwinkle and likely to back her, sources said.
On Monday, Preckwinkle will announce the creation of an exploratory committee for mayor, a move that would allow her to raise unlimited amounts of campaign cash toward a potential run. Unlike her county board race, the state campaign contribution limits in the mayor’s race were lifted earlier this year after Wilson decided to self-fund his campaign.
Creating the committee also symbolizes an attempt by Preckwinkle to solidify early front-runner status and would allow her to get a jump-start on Mendoza, who has said she remains focused on her comptroller race while declining to publicly discuss the possibility of running for mayor.
Gutierrez also is strongly considering a run after announcing his retirement from Congress earlier this year. Cook County Commissioner Jesus “Chuy” Garcia is running to replace him and is unlikely to jump into the mayor’s race, sources close to Garcia said. Garcia lost to Emanuel in the city’s first mayoral runoff election in 2015.
Gutierrez, 64, is a fiery, high-energy elected official whose Puerto Rican roots run deep. Known by the nickname El Gallito (Spanish for the little fighting rooster), Gutierrez long has been one of Chicago’s most colorful and controversial politicians. He has enjoyed a national profile in recent years as he regularly appears on cable TV to rail against Trump’s anti-immigration policies.
The drawbacks of a Gutierrez campaign: He hasn’t been in a competitive race in decades and would have to face questions about his close political and financial ties to Chicago’s real estate developers.
The Tribune reported in 2008 that Gutierrez personally lobbied then-Mayor Richard M. Daley to support a controversial development for a campaign contributor who had just lent the congressman $200,000 in a real estate deal. Gutierrez at the time said there was no connection between the loan and his efforts to get Daley to support the Galewood Yards project on the city’s West Side — a project that was not in Gutierrez’s district.
The project’s developer, Calvin Boender, was convicted in 2010 of federal corruption charges of bribing then-Ald. Isaac “Ike” Carothers to get Carothers’ support for the project. While Gutierrez’s name came up during Boender’s trial, he was not charged with any wrongdoing.
The Tribune also has reported that Gutierrez entered into a half dozen real estate deals with political donors, making about $421,000 from 2002 through 2008. Gutierrez said his real estate investments were appropriate.
Quigley, 59, who holds Emanuel’s former congressional seat, also is weighing whether there is a path to a mayoral victory. A former Cook County commissioner with a progressive North Side base, he’s risen through the ranks in Washington to earn a seat on two key panels, the House Intelligence and Appropriations committees.
To win, he would have to find a way to grow beyond his liberal base and raise enough money to drive up his name recognition substantially.
As for Bill Daley, the brother and son of two former mayors, he’s flirted with running for a high-profile office before, including 2002 and 2010 bids for governor, but never moved forward.
In 2013, he briefly entered the Democratic primary contest for governor, but then abruptly dropped out saying a bid “wasn’t the best thing for me” and vowed never to seek public office again. Now at 70 years old, Daley would have to explain what’s changed.
His surname also wouldn’t carry the same clout with the electorate it used to, as the party continues to drift further left from his centrist business background. Daley also would get tagged by progressives for his brother’s financial mismanagement of the city and his father’s role in Chicago becoming a deeply segregated city.
While the maneuvering for union support is well underway, the city’s wealthy corporate executives, developers, law firms and financial titans don’t have a natural candidate to get behind so far, several sources noted.
That was the strongest of Emanuel’s constituencies, as the mayor has successfully attracted scores of corporate headquarters and overseen a building boom that has left the downtown skyline dotted with cranes. Two sources close to the mayor suggested some of his top backers and donors in the business community could move in lockstep to one candidate — once he or she is identified.
“There are an awful lot of folks in the business community who are very concerned that the next mayor has the breadth of experience and credentials to preserve the business climate and grow the city while having to dive into the very difficult situation we have in our struggling neighborhoods,” said Reilly, the downtown alderman. “There is a concern here that many of the names being mentioned as candidates have very little to no experience in the private sector, and very few of the candidates have experience running very large organizations, let alone a 30,000-person operation like City Hall.
“So, they’re worried about that,” Reilly said, “because this job is a lot more than setting goals and giving speeches.”
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