With Brandon Johnson’s popularity barely above Meghan Markle levels, he is certain to face a host of challengers in the 2027 election. So far, only three — Mike Quigley, Maria Pappas, and Joe Holberg (who?) — have said that they’re running, but others have hardly made a secret of their interest (we see you, Susana Mendoza) and more will surely follow. Here’s how we rank the prospective candidates in terms of their chances.
1. Alexi Giannoulias: He hasn’t yet declared, but he has been raising $1 million a quarter in campaign funds, despite the fact that he has no competition for his current job as Illinois’s secretary of state. If he gets in the race, he’s the clear front-runner. In the words of one political consultant, he is the only prospective candidate who is “the complete package.” He has good relationships with progressives, including U.S. Representatives Chuy García and Jan Schakowsky. He’s worked in finance, a selling point as the city struggles with its debt. (He was CEO of Annoula Ventures, an investment company, which allowed him to rub elbows with the kind of folks who tend to donate big.) He’s also a friend of organized labor, which has endorsed him in past campaigns. As secretary of state, he’s done a more than competent job, opening new offices and making it easy for residents to get their Real IDs. And he’s used the office to bolster his anti–Donald Trump credentials, warning ICE agents that swapping out license plates to avoid detection is illegal. Secretary of state is a well-traveled path to higher office (which Chicago mayor arguably is): Alan Dixon went on to the U.S. Senate, and Jim Edgar and George Ryan became governors. Giannoulias has future gubernatorial candidate written all over him, but JB Pritzker isn’t going anywhere — other than perhaps to the White House.
2. Mike Quigley: Last time around, the U.S. representative passed on a mayoral run, saying he might have considered it if he were 10 years younger. Now, at 67, he’s four years older. Nonetheless, he plans to jump into the race. Though he’s still running for congressional re-election, he told WGN Radio in early January that after the March primary for that seat he’ll formally announce his mayoral campaign. He’ll make a formidable candidate: He’s progressive without being a leftist, which may be exactly what voters are looking for after four years of Johnson. Quigley hasn’t been shy to criticize the mayor’s fiscal management by calling for payroll cuts and union concessions to solve the city’s budget deficit. And his work in Congress has allowed him to position himself as a nemesis of Trump. Quigley holds the same congressional seat Rahm Emanuel did, but he’ll have to expand his appeal beyond the North Side in this race, the way Emanuel built relationships with Black voters as an Obama insider.
3. Susana Mendoza: She has done a bang-up job as Illinois comptroller, reducing the state’s backlog of unpaid bills from $16.7 billion to under $3 billion. She also never misses a chance to jab Johnson on X, posting recently: “Businesses hated Chicago’s $4-per-employee ‘head tax’ calling it a major reason NOT to move businesses to Chicago. … Mayor Johnson seeks not just to dig up this dreaded Frankenstein from the grave but to hike it up.” If voters are chiefly concerned with pocketbook issues a year from now — and they surely will be — Mendoza’s record of fiscal responsibility could be a big asset. On the downside, her relationship with the Latino community is not as strong as García’s or Luis Gutiérrez’s, so she doesn’t start with a particularly robust base.
4. Brandon Johnson: The mayor’s fundamental political mantra is that he cares about the interests of the least of us more than the interests of the most of us. We saw that in his failed referendum to increase a tax on real estate transactions of more than $1 million. We saw it in his battle with the City Council to reinstitute a corporate head tax rather than raise garbage collection fees. It’s idealistic, and it’s admirable, but it’s not politically advantageous, because the most of us is where the votes are. Johnson’s approval rating, at 31 percent in the fall, has rebounded from the teens. But he’s still the weakest mayor in modern memory, having lost control of the City Council, which unanimously bucked his plan for a property tax hike, then wrote its own budget. Johnson’s base consists of 30 to 40 percent of the Black vote, and a small cell of young democratic socialists. That’s probably not enough to get him into a runoff. But don’t count him out entirely: He still has the power of incumbency — and the reduced crime rates to campaign on.
5. Maria Pappas: A poll in September showed Pappas, the only serious announced candidate, beating Johnson 56 to 23 percent. But that’s head to head and says more about Johnson’s unpopularity than Pappas’s prospects. In 27 years as Cook County treasurer, the quirky Pappas has become best known for issuing an annual calendar featuring glamour portraits of … Maria Pappas. Working against her: She is 76, which is old to start a more demanding job. And she’d lose the Greek vote to Giannoulias.
6. Bill Conway: The alderperson of the upscale 34th Ward is personable, mediagenic, and rich. His father, William E. Conway Jr., is a billionaire who bankrolled his son’s unsuccessful 2020 bid for Cook County state’s attorney. He is also a prominent member of the City Council’s so-called Common Sense Caucus, which has clashed with Johnson on budget matters. Given his background, he’d be popular with the business community, which is desperate to defeat Johnson. However, no alder has been elected mayor since 1895. And if Giannoulias joins Quigley in the race, the white-guy lane will be awfully crowded.
7. Willie Wilson: Running for mayor is a quadrennial ego trip for this Near East Side businessman. It gives him a chance to burnish his name by handing out free gasoline and groceries. If he gets in again, his main role will be as spoiler to Johnson. He usually gets 10 percent of the vote, mostly from Black residents.
8. John Kelly Jr.: The powerhouse lobbyist, who once worked for Illinois Attorney General Jim Ryan, is mulling a run. He has even enlisted some star power: Former Blackhawk Chris Chelios is treasurer of his fundraising committee. But if there’s anyone voters consider a lower form of life than a politician, it’s a lobbyist. Even worse, Kelly is a lobbyist for a gambling company. (He represents Bally’s.) On the plus side: His job puts him in a position to hit up major donors.
9. Joe Holberg: The first candidate to publicly declare his intentions to run, he started out a math teacher on the West Side, then began a business out of the 1871 tech incubator that shows people how to manage their money. But he’s got no political experience, no political base, and no chance. Along with Kelly, he’ll be the “Who’s that?” guy at the debates.
