So who is thinking of running for mayor? And who should be thinking about it? “There’s no obvious candidate,” says a prominent Chicago political operative, meaning no one who has it all: the track record, the money, the name recognition, the charisma, the connections, the energy, and the guts.
But there are people who have many of these things, and based on what I’ve learned—in conversations over the past few weeks with several dozen elected officials, Democratic insiders, analysts, and consultants, most of whom didn’t want to be named for fear of political retribution by the mayor—if the decision had to be made today, Daley would have at least one challenger, and he might have several.
Of course the filing deadline for mayoral candidates isn’t until December 13, and the political world can turn several times between now and then.
Here, in no particular order, are ten players I’d keep a close eye on for now. These are the names I heard most from the movers and shakers, and either they’re considering a run or someone’s trying to recruit them for one. In some cases, it’s both.
Political insiders have been mentioning former city inspector general David Hoffman as a mayoral prospect for a couple years. The buzz spiked this past June, when he issued a blistering report on the city’s parking meter deal, and his strong second-place finish in the Democratic primary for U.S. Senate last month proved “he can run and run well,” as one operative put it. Local progressives have launched a Facebook group called “David Hoffman Needs to Run for Mayor!” and in a e-mailed thank-you note to his Senate supporters Hoffman left the door open for another campaign: “You should know that this defeat does not deter me from wanting to fight to improve the lives of those who don’t hold the reins of power and too often are shortchanged as a result,” he wrote.
Hoffman’s got some of his own money, but he just spent $1 million of it in the primary. He’s got a record of fighting for good government, but lots of aldermen and Democratic insiders write him off as a self-promoting pipsqueak. He’s smart and credible, but not always stirring. He might have to be drafted, but if he got into the race, Hoffman could make it very, very interesting.
Current city clerk Miguel del Valle was a favorite of progressives when he served in the state legislature (1987-2006), where he became known as an education advocate, but he shocked many of his biggest fans by letting Mayor Daley appoint him to the clerk’s job after incumbent James Laski quit under pressure. While Laski pleaded guilty to accepting bribes and served 11 months in federal prison, del Valle won election to a full term with the aid of a $100,000 donation from the mayor.
He’s mostly steered clear of politics since, focusing on bringing the clerk’s office into the computer age and ensuring that more of the City Council’s work is traceable online. If he chose to run, del Valle would start with a strong base in the Latino community, but he’d have to convince a few Daley haters that he hasn’t left his soul in a desk in the clerk’s office. That might not be too hard: some north-side liberal activists were talking del Valle up at a ward organization meeting last month. Del Valle wouldn’t comment for this story, but people close to him say he wouldn’t run unless Daley decided not to.
Cook County sheriff Tom Dart is a product of the local machine, specifically the 19th Ward Democratic organization. He got his job in 2006 through what looked like an inside deal: when his predecessor and patron, Michael Sheahan, abruptly announced that he wasn’t running for reelection, he arranged to have party regulars support Dart in his place.
But Dart has a new-school political style that appeals to progressives even as he keeps up his ties to Democratic insiders. Dart has made national headlines for refusing to evict families from foreclosed rental properties and for cracking down on dogfighting. Sheahan and his predecessors worked to keep life in the county jail off-limits to observers, but Dart has welcomed reporters and documentary filmmakers and vowed to improve conditions there.
“He knows how to promote himself and he’s got lots of progressive allies,” says one operative. “He’s got all kinds of up, all kinds of potential.” A spokesman says Dart is focused on “making a difference as sheriff,” but other sources in the know tell me he’s thinking over the mayor thing pretty carefully.
Cook County assessor James Houlihan has at least one thing going for him: a record of clashing with the mayor. The budgets Daley and his appointees set for the city, the public schools, the Park District, and the CTA determine what Chicagoans pay in property taxes—yet Daley frequently blames high taxes on Houlihan, whose office computes what everyone’s property is worth. In fact Houlihan has been an advocate for property tax reform and is one of the big reasons the state legislature passed a law giving home owners a break on rising assessments.
But Houlihan, who’s been assessor since 1997, decided not to run for reelection this year. And though he didn’t return my call, a source close to him says he’s mulling a mayoral bid. If he runs, Houlihan will have to spend lots of time reminding people who he is and countering the half-truths that Daley’s thrown out there about his role in the local tax system. But he’s respected by lots of good-government types, he’s won countywide office three times, and he’s got an Irish name, which never hurts in Chicago.
It’s never smart to count out state senator James Meeks. When he’s not pressing for education funding reform in Springfield, Meeks is the pastor of Salem Baptist Church of Chicago, the largest congregation in the state with some 20,000 members. Thousands of them are trained and authorized to register voters, which means Meeks is poised at any time to turn his congregation into a political army.
Four years ago he appeared to be doing just that, leading hundreds of Salem members in a series of demonstrations outside and even inside City Hall to demand that Daley do more to boost the quality of the city’s public schools. “If this problem isn’t addressed by February, we may have to look for other alternatives,” Meeks declared. But after Daley invited Meeks in for a private meeting in fall 2006, the senator stopped threatening an opposition campaign.
Meeks is a powerful speaker who’s well known in the black community, but he can be a loose cannon—he’s referred to Daley as a “slave master” and sometimes slips into a “white” accent when he’s criticizing politicians or business leaders during sermons. But to his credit he’s continued to pressure Daley and state officials to improve the public schools. On Chicago Tonight a few weeks ago he intensified the rhetoric, arguing that the Chicago Public Schools should be taken out of Daley’s control because they’re faring so poorly. And he reiterated the point when I got him on the phone the next day:
“I know Mayor Daley is powerful, and I know he gets angry when people oppose him. But at what point do we take on that mystique and say, ‘Maybe this isn’t his area of expertise? Maybe an education system should be run by an educator?'”
But he denied that he’s considering a campaign for mayor—sort of. “I don’t have any political aspirations beyond the office I have,” he said. “It’s amazing to me that anyone who speaks against a policy in Chicago is suddenly a candidate for mayor.” After a pause, he added, “But you never say never.”
The City Council is hardly a bastion of independence or progressivism, and no Daley loyalist in the bunch would run while the mayor’s in the race. (Should he retire, though, look out: “Hey, if he doesn’t run, everybody in here’s going for it,” one alderman says.)
But several of our bolder aldermen appear to be considering a challenge. Bob Fioretti of the Second Ward may be the most likely to pull the trigger. After just three years in office, Fioretti has become one of the real characters in local politics. His allure and his Achilles’ heel are the same—he knows how to work all sides. He’s comfortable cutting tax increment financing deals in the back room and then walking to the front and telling reporters about it. He’s pushed to improve oversight of city contracting and the budget but voted in favor of the parking meter deal. He’s a prosperous white lawyer who spends a lot of time in the poor neighborhoods of his ward and is fairly well known on black radio.
Skeptics say Fioretti hasn’t had a big enough victory to make a name for himself citywide, but it’s clear he’d be an exciting campaigner. He’s smart, funny, and likable, even if some of his council colleagues think he’s too slick for his own good. And he’s quickly built a broad base of support. He tells me that he’s focused on reelection as alderman—but then reminds me that his ward stretches from the Loop into impoverished parts of the south and west sides. “There’s nothing that affects the city that I’m not involved with in the Second Ward,” he says. “There are things we need to do in this city. We have no money in our budget and our school system is a billion dollars in debt, and I don’t hear anything about what we’re going to do about it.”
Seventh Ward alderman Sandi Jackson is one of the few African-American leaders widely considered able to make a credible run. She isn’t afraid to vote against the mayor’s budgets or power grabs, and as a candidate she’d be able to draw on the resources, connections, and political skills of her husband, Congressman Jackson, without the baggage of the Blago mess or the name Jesse Jackson, which Junior has told me makes some voters wary. Jackson is clearly ambitious—she contemplated a run for lieutenant governor last year—but like Fioretti and the other rookie aldermen she doesn’t have a long list of accomplishments to run on.
Plus, as I’ve noted before, she often appears bored in the council. She misses many of her committee meetings, was absent for the vote on the parking meter deal, and doesn’t have the highest visibility in her ward. “I have no plans to run for mayor in the great city of Chicago,” Jackson told me through a spokeswoman. “At this time my top priority is continuing to serve my constituents in the Seventh Ward as their alderman.” In other words, it’s possible.
Alderman Scott Waguespack, the new guy from the 32nd Ward, is much more low-key than his rookie colleagues. But his name is out there because he’s shown more independent leadership on key city issues than just about anybody we’ve got.
Let’s start with the big one: he was one of just five aldermen who voted against the parking meter deal. He even tried to warn the rest of the world: before the vote was taken he and his staff prepared a report that determined the city was about to leave at least a billion dollars on the table—exactly what Hoffman’s report concluded six months later. Waguespack has continued to criticize the meter deal, but he’s also been out front on other critical issues. He’s proposed legislation that would require third-party analysis and public hearings on any future asset lease deals. He’s also pushed for reforms in the TIF program and fought for infrastructure improvements in his ward. Waguespack isn’t saying what his plans are but has made no secret of his desire to see Daley defeated.
Party regulars are already annoyed by Waguespack’s thoughtful independence and have let him know they’re coming after his aldermanic seat; to run for mayor he’d need to raise lots of money and he’d have to get a lot more comfortable with speechifying and self-promotion. But with a well-organized grassroots campaign—well, he’d almost certainly doom his political career for as long as Daley is alive. But in doing so he might be able to make a statement.
Alderman Tom Allen is a curious case. He married into a political family, the Cullertons, who’ve held various offices on Chicago’s north side for decades. When his brother-in-law Thomas Cullerton died in 1993, Daley appointed Allen to finish his term as 38th Ward alderman. In the time since Allen has consistently been a member of the council majority that approves Daley’s plans and budgets. Occasionally he’s stuck his head out to bitch that the administration ignores aldermen, but he’s always retreated once the mayor makes nice with him.
In December, though, Allen gave the best speech of his career, ripping the administration on the meter deal, its top-down budgeting process, and its abuse of the TIF program. He’s been on the radar as a mayoral prospect ever since, and several fellow aldermen say he’s taking the idea seriously.
Allen told me he hasn’t decided anything. “I don’t plan my life too far in advance,” he says. When I ask him if that means there’s a chance he’ll run, he answers by listing his credentials: he’s sponsored legislation to cut down on illegal apartment conversions and boot 18-wheelers that park in the neighborhoods. He also sponsored the ordinance passed last year that requires a two-week waiting period between the time an asset privatization deal is proposed and when it’s voted on—an act of repentance, I’d say, for his own vote for the meter agreement.
“I’m going to continue to be vigilant in city government the way I’ve been vigilant since the day I got here,” he says. “We’ve got a lot of problems in the city right now. I haven’t really changed the way I conduct myself or voice my opinions. I make certain they’re not really my opinions—they’re the opinions of the people on the street. I try to represent the people.”
A big victory is always ideal, but Brendan Reilly impressed people by losing big. Reilly, the rookie alderman of the 42nd Ward, refused to rubber-stamp a Daley-supported plan to move the Chicago Children’s Museum from Navy Pier into Grant Park. Reilly held public meetings, met with constituents, negotiated with museum officials and the Daley administration, and studied the legal precedents before concluding that the plan “would set a dangerous precedent and open the floodgates for other private developers to lobby for their own locations on Grant Park.”
For his careful efforts, he was politically shat upon by the mayor, who suggested on several occasions that Reilly was siding with racists who simply didn’t want to see children of color in the park. Reilly lobbied his council colleagues for months, but in the end he couldn’t top the arm-twisting and favor-promising of Daley and his aides, and the museum plan was approved.
Nevertheless, Reilly came out looking like a statesman. Since then he’s juggled the demands of his downtown ward much more quietly—a wise move, since he needs to keep a lot of important businesspeople and Gold Coast residents happy. To the frustration of some progressives, Reilly is a true independent. He not only voted for the meter deal but defended it, yet he’s also told prosperous downtown property owners that he’s not signing off on the TIF handouts they want. “He’s showed that he isn’t faint of heart,” one operative says.
Still, he’s also made it clear that he’d prefer to work with Daley and get some things done. Reilly said he’s not interested in running for mayor. . Translation: He’s another who’d have to be drafted.  Â