Willie Wilson, a Chicago businessman and perennial mayoral candidate, has officially declared his intention to run for mayor in the 2027 election, marking his fourth bid for the city’s highest office. Wilson confirmed his candidacy on Wednesday, asserting that he will emphasize independent and conservative positions in his campaign.
Wilson, 78, rose from humble beginnings in Gilbert, Louisiana, to become one of the first Black McDonald’s franchise owners and a prominent local philanthropist. He has built a reputation in Chicago for his charitable efforts, including giving away millions of dollars in free gasoline, and is known for his tough talk on crime and opposition to tax increases.
“I’m a businessperson, and I don’t think, I know, I can straighten this out,” Wilson said in announcing his run. He criticized current city leadership and other potential candidates as lacking the experience necessary to manage Chicago effectively. He pledged to oppose any efforts to raise taxes, dismissing proposals to increase revenue as unsustainable.
Wilson’s campaigns have historically been self-funded. According to state records, his political fund held $28,613 at the end of June, with a total of $150,000 loaned personally to his latest effort. Despite consistently winning about 10% of the vote in past mayoral contests since 2015, Wilson has never advanced to a runoff. However, his support has influenced election outcomes, including the 2023 race where his fifth-place finish with 9% helped eliminate incumbent Mayor Lori Lightfoot after she had secured the majority of Black votes.
The upcoming election could see Wilson and incumbent Mayor Brandon Johnson competing for a similar voter base, particularly among Black Chicagoans, complicating the electoral dynamics. Johnson, the city’s first-term mayor, has not yet confirmed whether he will seek reelection in 2027, citing a desire to focus on governing.
Wilson has also courted controversy throughout his political career. He has never held elected office but has run unsuccessfully for positions including U.S. president and Illinois Senate. In 2018, a political reform group accused him of violating state election laws following a $200,000 giveaway at a South Side church; state officials later cleared him of wrongdoing.
Although Wilson identifies as a Democrat, his political views often align with conservative policies. During the 2023 mayoral race, he made provocative statements about policing, including calls to loosen restrictions on law enforcement officers and allowing them to pursue fleeing suspects “like rabbits.” While he expressed mixed opinions about former President Donald Trump—praising his support for Christian values and opposition to COVID-19 lockdowns, but criticizing his foreign policy and economic measures—Wilson has embraced a socially conservative platform within the context of Chicago politics.
Wilson also emphasized improving education, insisting that students should not advance grade levels without mastering reading and writing skills, though he did not offer specifics on how he would implement changes amid the city’s evolving control of the Chicago Board of Education.
With his combination of philanthropy, conservative rhetoric, and steady presence in Chicago’s mayoral races, Wilson aims to make a significant impact on the 2027 election despite the historical challenges he has faced in securing broad electoral support.