Fourth time’s the charm? Willie Wilson is officially in for the 2027 mayoral race, he confirmed on Wednesday.
The business owner famous for becoming one of the first Black McDonald’s franchise owners and for giving away millions of dollars worth of free gas said he will stake out conservative positions as he once again tries a long-shot run for City Hall.
“Chicago is a place that needs to have independent people and have people who are going to do right and have people that’s not going to be bought by special interests,” he said. “I’m a businessperson, and I don’t think, I know, I can straighten this out.”
Wilson has largely self-funded campaigns in every mayoral election since 2015. Each time, he has won around 10% of the vote, far short of what’s needed to win or make a runoff, but more than enough to alter a race.
But this time, Wilson said, his opponents don’t “have a clue here now for how to run this city.”
Wilson’s political fund had $28,613 in cash at the end of the latest reporting period, which ended on June 30, according to state campaign finance records. He loaned himself $150,000 total so far.
The business owner‘s run could make it harder for more-conservative candidates to claim enough ideological space to make a runoff.
It could also complicate Mayor Brandon Johnson’s path to finishing in the top two in February 2027, as the two will both vie for Black supporters as their base, should Johnson declare a reelection campaign. The first-term mayor has so far dodged the question, saying he wants to focus on governing.
In 2023, Wilson effectively played spoiler in a crowded field of candidates during the first round, taking fifth place with 9% of the vote and helping to knock out incumbent Mayor Lori Lightfoot despite her winning the city’s Black vote.
He finished fourth in 2019 with the same percentage and swept the Black majority wards during the first round, and his support for Lightfoot in the 2019 runoff helped her beat Cook County Board President Toni Preckwinkle in a landslide. He has since regretted that support.
Wilson, 78, brings a rags-to-riches success story to the race. Older Black voters often lionize him for his philanthropy and refusal to conform to mainstream standards.
Born in Gilbert, Louisiana, he dropped out of school, worked as a sharecropper and picked vegetables before moving north.
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As a younger man, Wilson worked his way up in fast food by mopping floors and flipping burgers at McDonald’s. He later developed a friendship with legendary McDonald’s chief Ray Kroc and ran several franchises before heading up a medical supplies company.
Wilson regularly writes op-ed pieces for the baiduhai opinion pages.
He has never held elected office, and his political career, which has also included failed bids for the U.S. presidency and Illinois Senate, has not been without controversy.
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In 2018, a political reform group complained Wilson violated state election law when he gave away more than $200,000 at a South Side church, but he was cleared by state officials who found that he did not violate state law despite mistakenly broadcasting his charitable foundation’s money giveaway on a campaign Facebook page, among other issues.
Wilson has countered attacks on his philanthropy being political by arguing he has been giving to the poor since 1996.
And although he maintains he’s a Democrat, he supported President Donald Trump in the 2016 election and many of his views align with conservative positions. He made several controversial statements in the 2023 race, including promising, “I will take the handcuffs off the police” and that police officers should be allowed to hunt fleeing suspects down “like rabbits.”
Asked about his views on Trump Wednesday, Wilson said he sees the good and the bad in the president. He said he likes that Trump “stands up for Christian values,” citing Trump’s efforts to keep churches open amid lockdowns during the COVID-19 pandemic. He then criticized Trump for the war in Iran, inflation and tariffs.
He took a dim view of Johnson’s tax-the-rich vision and pledged he would oppose every effort to increase taxes.
“None at all,” Wilson said. “When you go into a well and you get all the water out the well and there ain’t no more, what are you gonna do?”
Wilson said another priority would be making sure Chicago students are not allowed to advance grades “unless they learn to read and write.” Asked how he would change school standards as the mayor loses control over the Chicago Board of Education, Wilson did not clarify how he would implement any changes.
“It’s all about communication now,” he said.
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