With a burst of goodwill generated by his $1.2 million gasoline giveaways, millionaire businessman Willie Wilson joined the race on Monday to send Mayor Lori Lightfoot into political retirement after a single mandate.
Wilson has pledged to repeal Lightfoot’s vaccination warrant, hire four or five different police commissioners to tackle the relentless spike in violent crime, and eliminate red lights and speed cameras that rush motorists who can least get away. afford to pay the fines.
As he has done in all of his political races, Wilson also said he would blow fundraising caps in the 2023 mayoral race by making six-figure donations to the Willie Wilson campaign fund for the mayor he created in March 2018 and declared “active” on Monday. .
That could make it easier for Lightfoot to raise the $15 million some political watchers believe it will need to raise to defend its track record and boost its dismal public approval rating.
With the election less than a year away, Lightfoot has just $1.7 million in his main political account, even after his best fundraising quarter. For the most part, big money interests sit on the sidelines, apparently awaiting a nominee, possibly U.S. Representative Mike Quigley (D-Chicago).
Four years ago, Wilson won 13 of 18 black wards with his charitable donations. In the ensuing runoff, Lightfoot won all of those wards — and all 50 city wards — after Wilson endorsed her over County Council Chairman Toni Preckwinkle.
Wilson’s endorsement of Lightfoot sent a signal to his older, church-based constituency that, as he put it, “contracts, jobs and schools” were more important than the worries that they might have had on Lightfoot being a lesbian.
This time, Wilson’s candidacy could seriously hurt Lightfoot’s re-election chances, according to veteran political operative Victor Reyes, who is not involved in the mayoral race.
“His strongest base of support is older African-American women. This is where he would potentially come in – with the church people he appeals to. It hurts her considerably in the context that he could appeal to this older black base that seems to stick with her,” Reyes said.
“I wouldn’t overlook Willie Wilson. This will be, like, his second or third go-around. It doesn’t take much to get into a second round.
Given how important Wilson’s endorsement was to Lightfoot four years ago, Reyes said he found it somewhat surprising that she froze Wilson shortly after taking office.
“You don’t invite people into a doorway of the tent and just chase it out the back door,” Reyes said.
“He would have been a good ally to have.”
Like Ald. Ray Lopez (15th), who entered the mayoral race last week, Wilson portrayed Lightfoot as abrasive, dictatorial and unable to win the collaboration needed to solve Chicago’s thorniest issues.
“In the history of this country, I can’t think of a mayor I’ve ever heard of or seen with that type of personality. He’s a guy who, you can’t even tell if they put a name to it,” Wilson told the Sun-Times.
“You have to talk to people. You must communicate. There is no communication [with Lightfoot] unless it’s negative. If it doesn’t go her way, she takes it personally. If something is wrong with me, that’s okay. You have to talk to people. One person can’t make decisions for an entire city like Chicago.
Pressed on how he plans to restore public safety and the perception of it, Wilson picked up on the innovative idea he championed during his 2019 mayoral campaign.
“If I take  aldermen to run different wards, how can a superintendent of police run the whole town? I would put four out of five police superintendents and break it down. That would be a good start there. And all of them would report directly to me,” he said.
Wilson also promised to stop the exodus of Chicago police officers retiring faster than the city can hire replacements by dramatically increasing the starting salary and repealing Lightfoot’s vaccination mandate.
“You have to be able to sit down and talk to them. I don’t think you’re saying, ‘Okay. COVID-19 is here. If you don’t shoot, you won’t get paid,” Wilson said, two days before the deadline for base cops to get their second shot.
“These people put their lives and those of their families on the line for all of us. I would have preferred to see everyone come in and get tested. If they are negative, let them work. If they test positive, let them stay home for two or three days until they come back and get another test.
Wilson took aim at Lightfoot’s gift conveyor belt. They include: gas cards; public transport cards; free bikes, padlocks and helmets; security cameras and motion detectors and guaranteed basic income checks.
“I thought it was illegal to give taxpayers’ money away” for political purposes, Wilson said.
“I gave my own money out of my own pocket. It was not taxpayers’ money.
Yet another issue will be Lightfoot’s ever-evolving story about what she knew and when she knew it about the failed raid on social worker Anjanette Young’s wrong house.
“She lied about it,” he said.
“If you lie to the citizens who pay your salary, you are not real. If I lied to my boss about my job, they would fire me in the corporate world.
Lightfoot media consultant Eric Adelstein had no immediate comment.