Will Willie or won’t Willie? Chicago Mayor Brandon Johnson should be pondering that question if he plans to run for a second term in February 2027. Johnson’s campaign would be doomed if Willie Wilson were to decide to run again.
The mayoral electoral horse race is just 11 months away, and the contestants are already champing at the bit.
Politicos everywhere are talking down Johnson’s chances. His growing list of missteps, controversies and political battles make him a long shot for reelection. That’s the mantra you will hear from an array of Chicago politicians who are lining up to take him on.
Wilson, the famously successful business owner and philanthropist, is already teasing another mayoral bid. The outspoken African American is a deeply religious grade-school dropout with no-nonsense views. He boasts a following of dozens of pastors and other religious leaders who step up with him in his campaigns.
The day after the March 17 primary, Wilson took to Facebook with an announcement. He recently met with about 100 ministers who asked him if he planned to run, he said.
He told them: “If I’m going to run for mayor, or even consider running for mayor, I would need 150,000 people to 200,000 people to take and make a commitment to me. From $5 to $10 per person.”
“OK?” He will decide by June, he says.
OK.
Wilson has run for office five times, including three mayoral bids and stabs at the U.S. Senate and president. He has lost five times yet remains indefatigable. He snagged more than 10% of the citywide vote in his 2015 and 2019 mayoral bids. In 2023, he pulled in 9.1%. Those votes came overwhelmingly from African American voters on the city’s South and West sides.
This time around, absent Wilson or other prominent Black aspirants, those voters would be likely to vote for Johnson. If Wilson gets in, those votes will come right out of Johnson’s hide and leave a gaping hole in his chances.
Wilson is a fierce critic of the political establishment in Illinois, delivering op-eds for the Tribune in which he admonishes, badgers and demands that elected officials take up his policy prescriptions.
What makes him hugely popular are the Wilson giveaways. For years, he has doled out millions of dollars of his personal funds in free gas, groceries and gift cards to grateful Chicagoans who are struggling to make it.
So once again, fueled by an ego as big as his wallet, Wilson, 77, may be gearing up for another run.
Against this backdrop is a campaign field that will be carved up six ways from Sunday. Demographics are key. In diverse Chicago, white people, Latinos and African Americans are the largest ethnic voting groups.
At present, nearly all the potential contenders are white, and it looks like a slew of them might get into the race.
There is Illinois Secretary of State Alexi Giannoulias, whom Democrats just nominated for reelection. He is not yet committed to the mayor’s race but has raised more than $10 million in political contributions. He is widely expected to run. If he does, Giannoulias will be an instant front-runner.
Illinois Comptroller Susana Mendoza, who declined to run for reelection this year, is also expected to get in to try to corral the Latino vote.
Cook County Treasurer Maria Pappas declared her candidacy months ago, along with North Side U.S. Rep. Mike Quigley, small-business owner Liam Stanton and Joe Holberg, a former Chicago Public Schools math teacher who started a tech business.
Others reportedly looking at making a bid are 34th Ward Ald. Bill Conway, who has dubbed himself “New Day Conway,” and lobbyist John Kelly Jr. And likely more to come.
While they are all battling for votes from Chicagoans disenchanted with the Johnson regime, they should also be rooting for Wilson, to cut into Johnson’s base.
If I were them, I would be stuffing Wilson’s inbox with those $5 and $10 commitments and chanting, “Run, Willie, Run!”
Laura Washington is a political commentator and longtime Chicago journalist. Her columns appear in the Tribune each Wednesday. Write to her at LauraLauraWashington@gmail.com.
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