Lightfoot challenger Willie Wilson calls 2019 endorsement of mayor ‘a helluva mistake’

Willie Wilson, who owns a medical supply company, is known for his gas and food giveaways and for helping people pay their property taxes. His campaign is almost entirely self-funded.

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Janette Wilson, the wife of businessman and mayoral candidate Willie Wilson, believes her husband is a “modern day Moses.”

“My husband is a true visionary. He has the biggest heart in the world. He helps everyone,” she said of her husband, whom she has been married to for 25 years.

Wilson, who owns a medical supply company, has indeed helped many people, including giving away millions of dollars in gas and food to thousands of people last summer as gas prices soared.

Wilson’s foundation donated masks to Mount Sinai Hospital and six community organizations. He also donated masks to the Chicago police and fire departments.

In 2017, when a loan fund was created to help people behind on their property tax payments, he kicked in $150,000.

And in 2018, he even parked himself outside the Cook County treasurer’s office, handing out $500 checks to people to help them pay their property tax bills.

He wasn’t buying votes, he said then — just helping people.

Millionaire businessman Willie Wilson ran for mayor in 2019, finishing fourth overall, with 10.6% of the vote.

Millionaire businessman Willie Wilson ran for mayor in 2019, finishing fourth overall, with 10.6% of the vote. He endorsed Lori Lightfoot in the runoff, a decision he now regrets.

Ashlee Rezin/Sun-Times

“I would never use any dollars that I have or any other thing to buy votes. … Unless there’s a law that says that I cannot do it, I will continue to do it. We’ve got to help people,” he said at the time.

“These people are losing their homes. … Nobody says nothin’ about a politician when they give people a grant for land. Nobody said nothin’ to ’em when they give out turkeys. … Why hop on a person who’s been doing this for a long, long, long, long time?” he asked.

In launching his latest campaign, Wilson said he would donate the mayor’s $216,210 annual salary to churches and nonprofits, claiming he spends more on a weeklong cruise with his wife.

“You get me free of charge,” the 73-year-old candidate said.

Wilson also has been generous to his own campaign, pouring $5 million into it after donating $1.2 million to his failed 2019 mayoral bid.

In that race, Wilson won 13 of 18 Black wards, finishing fourth overall, with 10.6% of the vote. In the runoff, Lightfoot won all of those wards — and all 50 wards citywide — after Wilson endorsed her over Cook County Board President Toni Preckwinkle.

Wilson’s endorsement of Lightfoot sent a signal to his older, church-based constituency that, as he put it, “contracts and jobs and schools” were more important than concerns they may have about Lightfoot being a lesbian.

Of that endorsement, Wilson now says: “I made a helluva mistake. I’ve been very disappointed.”

In announcing his candidacy for this year’s race, Wilson knocked Lightfoot’s COVID-19 restrictions, including a vaccination mandate for city workers.

Lightfoot “doesn’t deserve a second chance because she messed around with religious freedom,” Wilson said, by shutting down churches while marijuana dispensaries stayed open.

Wilson vowed to repeal Lightfoot’s vaccination mandate, hire four or fivepolice superintendents to combat a surge in violent crime and eliminate red-light and speed cameras squeezing motorists who can least afford to pay the fines.

Businessman and former Chicago mayoral candidate Willie Wilson pumps donated gas for a driver Thursday morning at a BP gas station at 5201 W. Cermak Rd. in Cicero.

Businessman and Chicago mayoral candidate Willie Wilson pumps gas he donated to a driver in March.

Ashlee Rezin/Sun-Times

Wilson portrayed Lightfoot as abrasive, dictatorial and incapable of collaborating to solve Chicago’s most vexing problems.

“In the history of this country, I can’t think of a mayor that I’ve ever heard of or seen with that type of personality,” Wilson said.

“You’ve got to talk to people. You’ve got to communicate. There’s no communication [with Lightfoot] unless it’s negative. If it doesn’t go her way, she takes it personally. If something doesn’t go my way, it’s not a big deal. You’ve got to talk to people. One person can’t make decisions for a whole city like Chicago,” said Wilson.

Pressed on how he plans to restore public safety and the perception of it, Wilson reprised an idea he championed during his 2019 mayoral campaign.

“If it takes [50] aldermen to run different wards, how can one superintendent of police run the whole city? I would put four or five superintendents of police and break it down,” he said.

Wilson also took aim at Lightfoot’s giveaways, including gas and mass transit cards, bicycles, security cameras, motion detectors and guaranteed basic income checks.

“I thought it was against the law to give away the taxpayers’ dollars” for political purposes, Wilson said. “I gave my own money out of my own pocket. It wasn’t taxpayers’ dollars.”

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