Willie Wilson’s Path from Mayoral Candidate to Power Broker

With a mayoral runoff election on the horizon, Willie Wilson is the man of the hour - and he's not even running. Both candidates, Mayor Rahm Emanuel and Cook County Commissioner Jesús "Chuy" García, have been eagerly vying for Wilson's endorsement. Both are hoping that an endorsement by Wilson, who garnered more than 10 percent of the votes for mayor, will swing the African-American vote in their favor. Wilson, a self-made millionaire and entrepreneur, has said he's voting for García but has yet to make a formal candidate endorsement. 

Wilson was scheduled to appear on tonight’s broadcast of Chicago Tonight, but he cancelled his appearance. Wilson told us that he could not come on the show because he was meeting with both mayoral candidates.

Willie Wilson made headlines in January when he donated $1 million of his own money to his campaign for mayor. The move attracted attention to his run for office and cemented him as a viable candidate. And that hefty contribution didn't bankrupt Wilson. The African-American entrepreneur made millions from owning and operating five McDonald’s restaurants and a medical supply company. 

He’s the son of a Louisiana sharecropper and says he ran away from home at 13. Wilson started out as a janitor sweeping floors and rose through the ranks to own several fast food franchises. He’s a man of faith and has been known to recite prayers along the campaign trail. Wilson hosts a TV program on WGN called Singsation, which features him and others singing and dancing to gospel music.

Wilson had no political experience prior to running for mayor. He unapologetically owned up to his seventh-grade education and has said that he never finished his schooling because he wanted to show disadvantaged young people that you can be successful without graduating. Wilson’s drawl and informal speaking style has even drawn attention. While campaigning and speaking at a City Club event last month, the Chicago Sun-Times reported that Wilson addressed the audience by saying, “to the whiteys here, I want to let you know I ain’t prejudiced, alright?” Wilson denied using the term “whiteys,” but the paper stuck by their claim and even included an audio clip of the utterance in question.

Commentators were quick to jump on Wilson’s unpolished style and lack of specifics when questioned about the issues facing Chicago. When the Chicago Tribune editorial board mailed out questionnaires to all five mayoral candidates, Wilson answered multiple questions with the same answer: “As a new candidate I have to access the problem with my business expertise.”

Despite Wilson’s lack of political savvy, he came in third overall in the mayoral election with just over 10 percent of the total votes, beating out Bob Fioretti, the current-but-soon-departing alderman of the 2nd Ward, and William “Dock” Walls, the perennial mayoral candidate running for his third time. Neither Fioretti nor Walls were able to fund televised campaign ads. While 10 percent, or just over 50,000 ballots, may not seem like much on its own, Wilson’s run for office likely sent the mayoral race into an unprecedented runoff election between frontrunners Mayor Rahm Emanuel and Cook County Commissioner Jesús “Chuy” García.

In the map below, click on a ward to learn the percentage and number of votes Wilson received.

Source: Chicago Board of Elections
--Map by Linda Qiu and Kristen Thometz

In a surprising twist of political fate, Wilson has emerged as a kingmaker in the weeks leading up to the runoff election. Since Election Day, both the mayor and García have visited Wilson’s home numerous times to court his endorsement. Soon after losing the election, Wilson rescinded a promise he made on the eve of Election Day that he would endorse García. He’s stated that he’ll cast his personal vote for García, but has held off on endorsing a candidate before he consults with his supporters.

Emanuel’s support in the black community has visibly waned, as he received 42 percent of the votes from predominantly black wards, down from the 59 percent he received in 2011. García received only 26 percent of votes from these wards. This low showing could have been affected by Wilson’s appearance on the ballot, but in García’s case, it may also point to a deeper rift within minority communities.

Wilson referenced this tension in explaining why he retracted his promise to endorse García. “There’s a lot of animosity between Hispanics and blacks,” Wilson said. “African-Americans feel Hispanics are replacing them, even though they’ve been there the longest. They’re getting more contracts and more jobs.”

While the verdict is still out for who will receive Wilson’s support, one thing is certain: We haven’t seen the last of the sharecropper’s-son-turned-multimillionaire. In his election night concession speech, Wilson said the campaign allowed him to get to know Chicago better. He also vowed to remain in politics. 

Watch Wilson’s Chicago Tonight interview before the Feb. 24 election.

View a timeline of his career.

Update: Willie Wilson endorsed Jesús "Chuy" García for mayor of Chicago on March 11.