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Philanthropist and businessman Willie Wilson is once again running for mayor. (WTTW News)

Philanthropist and businessman Willie Wilson is once again running for mayor. It’s the third time he has sought the top job at City Hall. Wilson’s previous two mayoral bids were unsuccessful, as was his run for the U.S. Senate in 2020.

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Willie Wilson announces he will run for mayor of Chicago. (Heather Cherone/WTTW News)

Flanked by a large group of friends, supporters and religious officials, Willie Wilson made the announcement Monday in his condominium overlooking Lake Michigan and Navy Pier.

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(WTTW News)

If last week’s gas giveaway is any indication, people can expect to be idling in their cars for upwards of an hour or more Thursday as they wait their turn at the pump for Willie Wilson’s $1 million giveaway. 

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(WTTW News)

Chicago’s Office of Emergency Management and Communications and the Chicago Police Department say they’ve coordinated with Willie Wilson and his staff, and will provide city resources “to mitigate traffic conditions and ensure public safety.”

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U.S. Sen. Dick Durbin (WTTW News via CNN)

Sen. Dick Durbin has become one of the most powerful members of the Senate, but challengers say he is the ultimate Washington insider who’s lost sight of what’s best for Illinois. Meet two of those challengers.

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Willie Wilson appears on “Chicago Tonight” on March 28, 2018.

Wealthy businessman and Chicago pastor Willie Wilson announced Tuesday he’ll run as an independent against U.S. Sen. Dick Durbin. “As an independent Democrat I want to go into the belly of the beast in Washington, D.C.,” Wilson said.

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Willie Wilson announces his endorsement of Lori Lightfoot for mayor on March 8, 2019. (Chicago Tonight)

Businessman Willie Wilson, who finished fourth in his bid for Chicago mayor in the Feb. 26 election, announces his endorsement of former federal prosecutor Lori Lightfoot.

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Mayoral candidates Lori Lightfoot, left, and Toni Preckwinkle appear on “Chicago Tonight” on May 14, 2018 and Oct. 16, 2017, respectively.

Calling Tuesday’s election a referendum on the “crumbling political machine of the past,” former Chicago Police Board chair Lori Lightfoot claimed a spot in the historic mayoral runoff set for April 2.

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Paul Vallas, Willie Wilson, Toni Preckwinkle, Bill Daley and Susana Mendoza appear on “Chicago Tonight” on Monday, Feb. 18, 2019.

With a little more than one week left until the election for Chicago mayor, five of the perceived front-runners amped up their rhetoric in WTTW’s second of three candidate forums.

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Join us Monday at 7 p.m. for the second of three mayoral candidate forums, moderated by Phil Ponce. Watch on WTTW11 or live on our website, Facebook and YouTube.

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“This is not a political situation. We’ve been doing this for the last 10, 15, 20 years,” Chicago mayoral candidate Willie Wilson said Wednesday, Aug. 1, 2018 of his foundation’s giveaways of money. (Chicago Tonight)

A watchdog group takes action against the Chicago mayoral candidate’s campaign for behavior they believe is unethical and improper.

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Willie Wilson speaks to Chicago Tonight in 2015. (Chicago Tonight file photo)

The Chicago mayoral candidate faces criticism after handing out nearly $300,000 in cash and checks at a charity event. “I haven’t done anything but give my own money away,” Wilson said of the cash controversy.

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It might be hard to believe, but Chicago is less than one year away from its next mayoral election. Willie Wilson talks about why he’s looking to unseat Mayor Rahm Emanuel.

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Joel Weisman and his panel of journalists discuss U.S. Sen. Dick Durbin’s endorsement of Tammy Duckworth in the race for Senate and the widening field of candidates seeking to replace Mark Kirk who’s running for re-election, as well as businessman Willie Wilson’s announcement to run for president. 

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Millionaire businessman and one-time Chicago mayoral candidate Willie Wilson announced Monday he plans to run for president. Wilson says he’s running as an anti-tax Democrat and a candidate of the people

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Willie Wilson was scheduled to appear on tonight’s broadcast of Chicago Tonight, but he cancelled his appearance. Wilson told us that he could not come on the show because he was meeting with both mayoral candidates.