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 Monday.
Willie Wilson said he would donate the mayor’s $216,210 annual salary to churches and non-profits. He claimed he spends more money on a week-long cruise with his wife.
“You get me free of charge,” the 73-year-old candidate said.
To prove how serious he is about winning this time, Wilson said he deposited $5 million into the Willie Wilson for Mayor campaign fund he created in 2018 and declared active 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 political observers believe she will need to raise 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 — even after her best quarter of fundraising. For the most part, big money interests remain on the sidelines, apparently waiting for a 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.
Four years ago, Wilson won 13 of 18 Black wards on the strength of his charitable giving. Overall, he finished fourth, with 10.6% of the vote. In the runoff that followed, 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 had about Lightfoot being a lesbian.
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.
“You should not shut down churches because of COVID and not shut down the marijuana places. 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.”
Wilson’s candidacy could seriously damage Lightfoot’s re-election 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. It does significantly hurt her in the context that he might appeal to that older Black base that seems to be sticking with her,” 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 run-off.”
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.
“You don’t invite people in one door of the tent in order to just kick him out the back door,” Reyes said.
“He would have been a good ally to have.”
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. So him in the race is not helpful,” 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.”
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 winning the collaboration needed 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. It’s a type that, you can’t even know if they’ve put a name on it,” 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. You’ve got to talk to people. One person can’t make decisions for a whole city like Chicago.”
Pressed on how he plans to restore public safety and the perception of it, Wilson reprised the innovative idea he championed during his 2019 mayoral campaign.
“If I takes [50] aldermen to run different wards, how can one superintendent of police run the whole city? I would put four of 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 Chicago police officers retiring faster than the city can hire replacements by raising the starting salary substantially and repealing Lightfoot’s vaccine mandate.
“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 conveyor belt of giveaways, including gas cards, mass transit cards, bicycles, security cameras and 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.”
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.”
Keith Richardson, president of the Chicago Postal Worker’s Union, responded to Wilson’s candidacy on behalf of the Lightfoot campaign.
“Willie Wilson is no friend to Chicago workers — he has been a vocal Republican for years, throwing his support behind some of the city’s nastiest opponents: Bruce Rauner and Donald Trump,” Richardson was quoted as saying in a statement.
“Willie Wilson has been a vocal opponent against the labor movement, which has raised wages, offered paid sick leave and improved quality of life for Black and Brown communities. As Chicago moves into a post-COVID area, we need a mayor that will create jobs and opportunities for all Chicagoans, not one who is going to give himself massive tax breaks and wage a war on Chicago workers.”
As for his party leanings, Wilson refused to say whom he voted for in the 2020 presidential election.
“Why do you ask me that? That’s personal, isn’t it?” he said.
Then he was asked if he Joe Biden was fairly elected president.
“You’ve never heard me say it was an unfair election,” Wilson said, adding: “I won’t answer if I don’t want to answer. ... I’m running for mayor of Chicago — not president.”
