It is Wilson's third attempt at the mayor's office. He previously ran in 2015 and 2019, garnering around 10% of the vote in 2019.
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Businessman Willie Wilson's 2nd Chicago gas giveaway smoother but not without hiccups
Over the last few weeks, Wilson held gas giveaways to help commuters. At his most recent event he talked about how Mayor Lori Lightfoot's plan to offer prepaid gas cards to residents will do little to help most people struggling to fill their tanks.
WATCH: Willie Wilson officially announces mayoral run
Willie Wilson makes official mayoral run announcement
Wilson said he is pumping $5 million of his own money into his campaign to get it started. He gathered with clergy and other supporters in his high rise condo along the Chicago River to kick off the campaign.
"You know, the media, you all would be here if I wasn't a threat. We're gonna win it this time," he said.
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While Wilson endorsed Lightfoot when she ran for mayor, he quickly expressed his disappointment and criticized her efforts at reducing crime across the city.
"I made a mistake, I made a hell of a mistake, and I have to say that because I've been very disappointed," he said of the mayor Monday.
Alderman Ray Lopez announces 2023 Chicago mayoral run
When asked why he thinks he can win this time, Wilson said, "I don't need to run for mayor to get a paycheck. My wanting to do this is to serve the community. We want to bring all race, creed and color together."
Wilson has also run a failed race for president and most recently for Senate against Dick Durbin in 2020.
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Mayor Lori Lightfoot still has not officially announced that she is running for reelection, but is expected to sometime soon.
Monday morning in a campaign email she announced some new hires for her political team.... A spokeswoman saying"... as we gear up ahead of a reelection announcement."
How will Willie WIlson's 3rd time running for mayor be different?
She took a swipe at Wilson for his high profile charity work at a Monday afternoon event.
"You judge people by what they do when people aren't looking, not what they do when they see the spotlight on them," she said.
Wilson's candidacy announcement comes after Alderman Ray Lopez jumped in the race last week. Chicago police officer Frederick Collins was the first to announce he was running in February.