Chicago mayoral race: Will third time be a charm for Willie Wilson?

After running for Chicago mayor in 2015 and 2019 and failing to make the runoff election, wealthy businessman Willie Wilson announced during a Monday morning press conference he's going to run for the job again.

"I don't need to run for mayor to get a paycheck," Wilson said. "My wanting to do this is to serve communities."

Four years ago, Wilson estimated his net worth at up to $60 million.


So is Wilson becoming one of those perennial candidates who just likes to run or does he have a legitimate shot?

He's also run for U.S. Senator and for President of the United States, unsuccessfully. But he could have a bigger impact this time, especially given his popularity among voters in Chicago's politically pivotal Black community.

"We gotta make sure that the communities work together. One person cannot solve the problem of two or three million people or more. It takes togetherness," Wilson said.


"One person cannot fix the crime by itself. One person cannot fix all the economic that we particularly need or the education system, but one person can open the doors and communicate and that people can have input and to put in."

Wilson’s recent multimillion dollar gasoline giveaways have become part of his political trademark and have added to his standing and public attention. But they have also drawn ridicule from Mayor Lori Lightfoot and some of her allies for causing long lines and making people wake up early to get in those lines.

But Wilson is promising to do it again, even if the city imposes new rules to make it more difficult.

"If Chicago don't allow me to do it again, try to put up some roadblocks, then we’ll just go over in Indiana and suburban areas and have the people in Chicago come out there and get gas. We'll do what it takes," Wilson said.

There’s currently no word on whether that sort of gasoline giveaway might be a regular feature.

There is one other candidate as he contemplates another round of gasoline giveaways. Ald. Ray Lopez from the South Side’s 15th Ward jumped in a few days ago and is among perhaps a half dozen serious candidates.