Businessman Willie Wilson says he is again attempting to be the next mayor of Chicago, adding his name to what’s expected to be a long list of candidates vying to replace incumbent Mayor Lori Lightfoot.
Flanked by a group of pastors from throughout the city, Wilson said at a news conference Monday he’s starting by donating $5 million to his campaign. Wilson also talked about unifying Chicagoans across racial demographics and stopping crime, but was light on details, saying he’s going to take ideas from community members.
Wilson is most recently known for his cash and gas giveaways, during which he has handed out direct funds to residents. When gas prices recently soared after Russia’s attack on Ukraine, Wilson distributed $1.2 million in gas to residents, causing traffic jams and long lines at the select gas stations that hosted his giveaway.
Shortly after Wilson’s giveaway, Lightfoot announced her own proposal for the city to give away $7.5 million in prepaid gas cards. In a seemingly indirect criticism of Wilson’s initiative, Lightfoot said residents would no longer need to line up at 4 a.m. to wait for gas discounts. Her plan still needs approval from the City Council.
In turn, Wilson criticized Lightfoot’s effort, saying she should tackle the issue of rising gas by addressing the city’s gas tax, not just through a number of limited prepaid gas cards.
In 2018, Wilson handed out $200,000 to residents while running for mayor, prompting complaints he violated election laws by attempting to buy votes. The Illinois State Board of Elections determined the cash giveaway did not violate state campaign finance law.
On Monday, Wilson faced questions from reporters about his voting history and his political leaning. Wilson previously revealed that he voted for Donald Trump in the 2016 election. He declined to answer who he voted for in 2020, and a question about whether Joe Biden was fairly elected president of the United States.
“How would I know?” Wilson said, but added he has never said the 2020 election was unfair.
Wilson has never held public office, despite multiple attempts at doing so. He lost previous bids for Chicago mayor in 2015 and 2019. He also launched a failed bid for president in 2016 and lost a third party campaign for Illinois’ U.S. Senate seat in 2020.
In 2019, Wilson actually endorsed Lightfoot during her run-off victory over Cook County Board President Toni Preckwinkle. He said Monday that endorsement was a “hell of a mistake.”
“I’m not going to go around and criticize her because … you know how she has done so far better than I do. But if I had to look back … I made a mistake. I made a hell of a mistake,” he said.
Wilson is the second person to throw his hat in the race for mayor in the past week. Ald. Raymond Lopez recently said he’s mounting a run for mayor, outlining public safety as a major priority. Lightfoot has not yet officially announced she is running for reelection, but she has been actively fundraising and on Monday announced new hires to her political operation.
Mariah Woelfel covers Chicago politics at WBEZ. You can follow her on Twitter @MariahWoelfel.