Willie Wilson is promising another $1 million in free gas but his giveaways raise campaign questions

Chicago businessman and mayoral candidate Willie Wilson announced he will be giving away another $1 million in gas this Saturday, a move that will provide some relief for city motorists but also, once again, raises thorny questions about Wilson providing handouts to potential voters.

In March, Wilson gave away $1.2 million in free gas over two events at several city and suburban gas stations. Citing skyrocketing gasoline prices in recent months, Wilson — who has a history of practicing sometimes unorthodox, grassroots philanthropy — said he is just trying to help struggling residents.

But this most recent gas giveaway announcement on Tuesday comes just one week after Wilson formally declared his intention in 2023 to succeed Lori Lightfoot as Chicago’s mayor, the third time Wilson will be a Chicago mayoral candidate.

Four years ago, state election officials cleared Wilson of violating election law after he was accused as a mayoral candidate of improperly mixing politics and charity work when he handed out tens of thousands of dollars to potential voters at a South Side church.

On Tuesday, Wilson said he wasn’t worried about anyone raising similar claims this time around because he’s been “consistent” about giving money to those in need for more than 25 years. Those who might have an issue with his philanthropy leading up to and during elections in which he is a candidate should “look at themselves,” he said.

“Go out there and help those people who are homeless, that don’t have food, that are still sick with COVID-19,” he said. “Go out there with the people who can’t get to work, who can’t get to a babysitter. Go out there and tell those people you stopped giving because of some political season. I’m not that way.”

Vote-buying is illegal, but candidates and political figures are generally allowed to give away money or other resources as long as it isn’t explicitly tied to politics.

Wilson came under scrutiny in 2018 he handed out more than $200,000 in cash and checks to people at a South Side church for an event he attended with then-Gov. Bruce Rauner.

The Illinois Campaign for Political Reform, a watchdog organization now called Reform for Illinois, filed a complaint with the Illinois State Board of Elections that alleged Wilson violated state law by not reporting the money he gave away at the church as an in-kind contribution to Wilson’s mayoral political committee.

While the Wilson campaign maintained the nonprofit Dr. Willie Wilson Foundation is a separate organization from his political operation, the political reform group noted the two groups used the same spokesman and that scenes from the July 2018 event were shown on the Wilson for Mayor political campaign’s Facebook page.

The elections board eventually rejected the complaint, agreeing with the Wilson campaign that the church giveaway was part of a long-established practice by Wilson and unrelated to the campaign.

Alisa Kaplan, Reform for Illinois’ current executive director, said “voters can draw their own conclusions about the ethical implications of gas or cash giveaways during an election, regardless of whether they’re properly disclosed.”

“You could certainly see where reasonable observers might think it comes close to vote-buying, but there’s nothing in the law that prohibits it if it’s properly disclosed and candidates aren’t pretty explicitly soliciting or ‘influencing’ votes,” Kaplan said. “And of course elected officials do things like turkey giveaways under the umbrella of ‘charity.’ You couldn’t blame anyone, especially people in need, for taking advantage of these events, but they certainly raise ethical questions about the use of charity and giveaways to boost the candidates’ electoral chances.”

The ability to give away large sums of money is “yet another advantage the wealthy have in electoral politics,” and the “interplay between ‘charity’ and campaigning may become a bigger and bigger problem,” Kaplan said.

Brian Pryor, a spokesman for the state elections board, said the board can’t provide legal advice but can give out general guidelines.

“In order to avoid problems, our campaign disclosure staff suggests the charitable giveaway should be kept separate from political activities. The recommendation is that there should be no campaign signs, campaign speeches or other advertising related to Mr. Wilson’s candidacy, as well as no appeals to vote for him,” Pryor said. “The same would go for promotion of the giveaway event.”

Southwest Side Ald. Raymond Lopez, 15th, who has also announced his candidacy for mayor in the 2023 elections, said Wilson’s philanthropy “is well known” and didn’t take issue with this week’s announced gas giveaway.

“To say you have a problem with it now would be politics in and of itself,” Lopez said this week. “I know Dr. Wilson has helped our wards, our city, with his efforts, most notably during the pandemic when he donated masks to the city of Chicago. Nobody questioned if it was politics.”

In the 2018 case, a state hearing officer, James Tenuto, said the church cash giveaway event didn’t violate state law for various reasons, including that there were no political speeches at the event, there was no requirement recipients be registered voters, people in attendance weren’t urged to vote and suburban taxpayers made up 25% of the recipients.

”Most significantly, Willie Wilson has a 30-year history of charitable donations throughout the country,” Tenuto said.

Wilson celebrated the election board’s favorable ruling by promising to do it again and criticizing then-Mayor Rahm Emanuel, who was not party to the complaint.

”I don’t usually curse, but these guys, Rahm Emanuel, (this) lawyer guy here, they’re a bunch of a------- (for) even thinking of doing something like this,” Wilson said.

Former state senator and paid Wilson adviser Rickey HendonCQ also defended Wilson by denying that he was buying votes.

“They’ve accused this man of buying votes, and I just have to say it … buying votes on the West Side, South Side, votes about $5, $10,” said Hendon. “So if Willie Wilson is giving somebody $3,000, as an adviser, I’d be like, you’re overpaying by 1,500%. Because if we wanted to buy votes, it’s 5, 10 bucks on the West Side and South Side, so let’s just be real about that.”

After Wilson’s first gas giveaways, Lightfoot followed by proposing $12.5 million in city funds be used for 50,000 prepaid gas cards worth $150 each as well 100,000 passes that will cover $50 worth of CTA fares. The plan still needs to be approved by the City Council, and she denied her move was a reaction to Wilson.

In announcing his latest gas donation, Wilson said a list of participating gas stations will be made available on his Facebook page. He also called on city and state leaders to temporarily waive taxes on gasoline and asked gas station owners to lower their prices during Saturday’s giveaway so that more people can benefit.

“It saddens my heart to see people who cannot get to work because of gasoline,” Wilson said. “I’m going to go this Saturday, and we’re going to pump some more gas like we did last time.”

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