Willie Wilson joins 2023 race for mayor

With a $5 million contribution to himself and a burst of goodwill generated by his gas giveaways, millionaire businessman Willie Wilson on Monday joined the race to send Mayor Lori Lightfoot into political retirement after a single term.

“My husband is a true visionary. He has the biggest heart in the world. He helps everyone. He is the modern-day Moses,” Janette Wilson, the candidate’s wife of 25 years, said in introducing her husband at their downtown penthouse.

Willie 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.

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To prove how serious he is, Wilson said he deposited $5 million into the Willie Wilson for Mayor campaign fund he created in 2018 and declared active again on Monday.

That blows the cap on all candidates’ fundraising in the 2023 mayoral race, potentially making it easier for Lightfoot to raise the $15 million some observers believe she will need to defend her record and boost her dismal public approval rating.

With the election less than a year away, Lightfoot has just $1.7 million in her primary political account. For the most part, big-money interests remain on the sidelines, apparently awaiting another candidate, possibly U.S. Rep. Mike Quigley, D-Ill.

“I’m putting my money where my mouth is,” said Wilson, who donated $1.2 million to his 2019 mayoral campaign.

Anthony Vazquez/Sun-Times

During an unrelated news conference Monday, Lightfoot touted her “record of accomplishments,” adding: “There is that narrative that some like to perpetuate. But what I would say is, look at the record of incredible success through a global pandemic and economic meltdown and all of the other challenges that we faced over the last two years.”

Lightfoot also stood behind the vaccine mandate for city employees, which Wilson vowed to abolish.

“Every single court, every single arbitrator who has looked at this has said without qualifications that it was our right as the employer to make sure that we are doing everything we can to keep the workplace safe,” Lightfoot said. “And we have heard from our employees who are grateful because they don’t want to come back to a workplace where they’re not safe.”

Three years ago, 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 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 gay.

Of that endorsement, Wilson said Monday: “I made a mistake. I made a hell of a mistake. I’ve been very disappointed.”

He added, “I don’t have any bitterness because that ain’t Christian-like to have. ... I wish her the best in whatever she has to do. But she’s got to leave City Hall.”

Wilson was introduced by a parade of pastors along with a handful of business leaders backing his candidacy.

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.

“Our religion is sacred. Stay away from our religion. The lady had the nerve to come into churches and tell them to close down and give them tickets [if they refused]. I resent that.”

Lightfoot countered that no decisions she’s made over the last two years have been easy, but they have been “guided by the data and the science, all in the interest of making sure that we save peoples’ lives in, I hope, the biggest … public health challenge of our lifetime,” she said.

Ashlee Rezin/Sun-Times

Wilson’s candidacy could seriously damage Lightfoot’s reelection chances, according to veteran political operative Victor Reyes, who is not involved in the mayoral race.

“Her strongest base of support is older African American women. That’s where he would potentially cut in — with the church folks he appeals to,” Reyes said.

“I wouldn’t discount Willie Wilson. This will be, like, his second or third go-around. It doesn’t take much to get into a runoff.”

Given how pivotal Wilson’s endorsement was to Lightfoot four years ago, Reyes said he finds it somewhat astounding that she froze Wilson out shortly after taking office.

“He would have been a good ally to have,” Reyes said.

Veteran political strategist David Axelrod has helped to elect mayors, senators and the nation’s first Black president.

He said Wilson “has a following, particularly in the African American community” and has potential to really hurt Lightfoot.

“Though her constituency is not limited to the African American community, she’s gonna need to maximize her support there,” Axelrod said.

“In a crowded field, he could be a factor. No doubt about it. ... One thing that he brings is resources. And he seems willing to spend them. In politics, that makes a difference.”

Anthony Vazquez/Sun-Times

In a wide-ranging interview with the Sun-Times on Friday, Wilson vowed to repeal Lightfoot’s vaccine mandate, hire four or five different police superintendents to combat the unrelenting surge of violent crime and eliminate red-light and speed cameras squeezing motorists who can least afford to pay the fines.

Like Ald. Ray Lopez (15th), who jumped into the mayor’s race last week, 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 in that Friday interview.

“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.”

Ashlee Rezin/Sun-Times

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. That would be a good start right there. And all of ’em would report direct to me,” he said.

Wilson also vowed to stop the exodus of retiring Chicago police officers. A higher starting salary would help, as would repealing the vaccine mandate, he said.

“You have to be able to sit down and talk with them. I don’t think you say, ‘OK, COVID-19 is here. If you don’t take the shot, you’re not gonna get paid,’” Wilson said, two days before the deadline for rank-and-file police officers to get their second shot.

“These people have put their lives and their families’ lives on the line for all of us. I would have rather seen everybody come in and get tested. If they test negative, then let ’em work. If they test positive, then let ’em stay home for two or three days until they come back and get another test.”

Wilson also took aim at Lightfoot’s giveaways, including gas cards, 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.”

Ashlee Rezin/Sun-Times

Yet another issue will be Lightfoot’s ever-changing story about what she knew, and when, about the botched police raid on the home of social worker Anjanette Young.

“She lied about it straight up,” he said.

“If you lie to the citizens who pay your salary, you ain’t real. If I would lie to my boss on my job, they would fire me in the corporate world.”

In defending her record, Lightfoot argued there has “never been a mayor in the city’s history” who has “invested as much as my administration has” in majority-Black wards.

“There are some people who think that’s a bad thing. They want their city back. ‘They’ being the people who profited from resources being clustered among the clouted few. … If you don’t create legitimate opportunities for employment and engagement in our neighborhoods, you are gonna continue to see this constant, perpetual cycle of violence as we have seen for decades,” the mayor said.

“We’re on the right path. This is about the future of our city. This is about who we want to be coming out of this pandemic and whether or not we’re gonna bring everybody along or whether or not we’re gonna return to the days when a few people got all the resources on the table and there was no room for anybody else. That’s not the city that I want. And I don’t think that’s the city that the vast majority of residents want. They want a city that’s fair.”