Willie Wilson announces he's running for Chicago mayor in 2027

Willie Wilson is making another run for mayor in 2027, becoming the 10th candidate to enter the race.

Few people know what running for mayor is really like better than Wilson. He's done this before.

The 78-year-old millionaire businessman has run for mayor three times before — in 2015, 2019, and 2023.

He's wealthy enough to self-fund his campaign. He said he'll be beholden to no special interests.

"I'm my own person. That's why I use my own resources. I don't answer anybody anymore," Wilson said.

Asked why he's running for mayor for a fourth time, Wilson said, "The condition of Chicago."

"You know, high taxes, crime, education," he said. "People sold out to special interest groups, and the wider community continues to suffer, and it would be a crime if I did not do it. You know, win, lose or draw, I win, because I'm out there to bring the truth out. I always tell people, like, I'm not bought. I spend my own money, you know. I never think I lose. People say, 'Well, this is your fourth time.' I don't look at it that way."

Wilson is a self-made multi-millionaire who made a name by giving away gas, groceries and regularly running for public office, but never winning.

He denied any suggestion by some of his critics that he's entering the race to shift support away from incumbent Mayor Brandon Johnson to help another candidate in the race.

"I think those people are just probably mentally ill," he said. "Why would I need to do anything? I have my own resources. I use my own resources."

Asked what he does want to achieve, Wilson said, "I want every citizen of Chicago to be able to benefit and have an opportunity and a hope for a job, career, training."

Wilson has never made the runoff in a mayoral election in the past, and he has garnered roughly the same percentage of the vote every time he has run for mayor — 10.7% in 2015, 10.6% in 2019, 9.1% in 2023.

But he said he has a duty to run for mayor again because Chicago changes every year and every day with persistent problems, and action is not being taken.

Wilson said he would stand up for both businesses and residents.

"I mean like, businesses, top priority — help them to stay here, and have them not to just be leaving out in droves; help people to stay here; help people to buy their groceries, their gasoline in Chicago and not in Indiana," he said.

How would he keep residents' dollars in Chicago?

"Well you lower the prices, taxes. You cannot keep taxes going up as they're going up now, running people out. You've got to lower the taxes to keep people here and want to stay here. You cannot pay these taxes," he said. "Look, the parking lot, up 36% to park down here, you know. So people go to suburban. Michigan Avenue basically is paying for the whole city of Chicago."

With the city facing a massive budget deficit, Wilson said there are ways for the city to go on providing essential services while freezing or lowering taxes.

"Well one thing, you have to bid out your contracts. You have to ask these major corporations who have these contracts to be inclusion. You've got to work with the union. You've got to take your employees that are here, and more people that is here not working, train. You must educate the people in school, that in these Chicago Public Schools to be able to get trained, not to graduate them and don't know how to read and write. Build your workforce like businesspeople do."

Wilson said a recent poll shows him and Johnson with nearly identical support among voters.

"It showed him and I in a dead heat, and I'm not even the mayor. I'm a citizen," Wilson said.

He credited Johnson with selecting Larry Snelling as police superintendent, helping bring crime down in Chicago the last few years. He even said he would like to see Snelling, who recently retired, come back.

But as for Mayor Johnson, Wilson argued the mayor's loyalty is not to the average resident.

"I think Mayor Johnson is the mayor of the Chicago Teachers Union," Wilson said. "I think he's more focused on that than he's doing the regular citizen."

He's critical of opponents in the race, like Illinois Secretary of State Alexi Giannoulias and U.S. Rep. Mike Quigley, who are running for re-election to their current positions while also launching bids for mayor.

"I think it is a moral issue," he said. "I think what the law says is right is not always right, right? You can't serve two masters at the same time."

He's also critical of Johnson, who has yet to announce if he's running for re-election. Wilson said the mayor's rapid loss of some of his top cabinet members in recent months is a red flag.

"Mismanagement," Wilson said. "You have to change your direction, but first you must recognize your problem. If you don't recognize your problem, you always have these problems. … I definitely don't think he recognized the problem. I think that this was one-sided in what he's doing."

Wilson bills himself as an independent. In addition to his three previous bids for mayor, Wilson also launched a bid for president as a Democrat in 2016, and ran for U.S. Senate under the "Willie Wilson Party" banner in 2020.

He said he voted for Donald Trump for president in 2016 but not in 2020 or 2024.

He also said he disagreed with Operation Midway Blitz, the Trump administration's high-profile immigration crackdown in Chicago last year, but would have used the Illinois National Guard to help fight crime in Chicago.

"I would have took advantage of that support," Wilson said.

A total of 10 candidates have now declared their runs for mayor. Mayor Johnson still has not confirmed whether or not he is running for a second term.