Willie Wilson Isn’t Giving Up Anytime Soon

Dr. Willie Wilson (I-Chicago) ran as a Democrat for Chicago Mayor in 2015 and 2019, U.S. President in 2016, and now has launched an independent bid for U.S. Senate in Illinois in 2020.

Dr. Willie Wilson (I-Chicago) ran as a Democrat for Chicago Mayor in 2015 and 2019, U.S. President in 2016, and now has launched an independent bid for U.S. Senate in Illinois in 2020.

Buddy Guy said when he came to Chicago, “I was looking for a dime and I found a quarter”. Willie Wilson found a million dollars.

Like the blues legend, Wilson came from the Deep South to Chicago looking for opportunity. Wilson turned a job at McDonalds into his own franchise and a blossoming business enterprise.

He has the rags to riches story that writes political ads for itself. Now, after two failed mayoral bids and a short-lived presidential run, Wilson is running for US Senate.

“(I’m) trying to bring jobs and make corporations back to Illinois versus running them out of Illinois,” Wilson said during a Zoom interview in the car in between public appearances. “I’m a small businessperson as well. A lot of these small businesses are taxed to death and when they’re taxed to death they have to close down and leave out of the state.”

Wilson, 73, is on his own for this race. He’s no longer running as a Democrat, but as an independent. The self-made millionaire made himself a political party as well, the Willie Wilson Party.

Standing in his way is the senior senator from Illinois, Dick Durbin. Durbin has not only been in that seat since 1997, he’s the second most powerful Democrat in the upper chamber. Wilson has his work cut out for him: the Cook Political Report rated the race as “Solid D.”

“I decided to run because he’s been there 37 years,” Wilson said of Durbin’s time in both the US House and Senate. “Too long for anybody to be a career politician.”

Wilson’s run may be quixotic, but his previous failed bids haven’t dampened his aspirations.

“Abraham Lincoln ran 21 times before he became president and he lost 21 times,” he said.

For the record, Lincoln was elected to the Illinois House in 1834, 1836, 1838, and 1840. He was elected to Congress in 1846. Lincoln did lose several times en route to the White House including his legendary

1858 Senate race with Stephen A. Douglas. The larger point remains Wilson isn’t going anywhere, no matter the result of this election.

“I have to get up and keep going because I believe we’re put on Earth here to help other people and I’m not going to sit around and let it pass me by without doing everything at least 100 percent that I’m able to do to help others and by helping others, you really help yourself.”

The biggest issue in Washington right now is filling the vacancy on the US Supreme Court left by the late Ruth Bader Ginsburg. On this issue, Wilson doesn’t stray far from Durbin.

“I would like to see them wait for the new president, the same way when Barack Obama was president,” he said. “They made him wait. They fought him.”

Ben Garbarek of the Illinois talks to Willie Wilson, a Chicago businessman and philanthropist who has taken on two runs for Chicago Mayor, a short-lived atte...

Right before speaking with The Illinoize, Wilson was handing out gift cards at an apartment complex on the south side of Chicago. During his 2019 run for Chicago mayor, he handed out money to churchgoers. His critics accused him of buying votes but the Illinois State Board of Elections ultimately cleared him of breaking any campaign finance laws because the money had come from his non-profit foundation.

Wilson defends giving out money saying he’s been doing it since the mid-1990’s, years before he ever ran for elected office.

“I’ve been giving away millions and millions of dollars all during those times,” Wilson said. I’d say to the critics they ought to get out and help others. I still give. What do the critics say when I gave away 27 million face masks when I could have sold them at a value of $18 million, but they all needed face masks. I could take $18 million and buy all the ads I need to buy.”

Barring an epic upset, Durbin will cruise to re-election. FEC records show his campaign with around $5.5 million cash on hand compared to around $20,000 for Republican challenger Mark Curran and $45,000 for Wilson. Wilson said he would spend $5 million of his own money on the race.

The question is likely not whether he can win, but if he can single-handedly beat the beleaguered Illinois Republican Party and finish in second. Regardless of the outcome, Wilson said he has an obligation to keep running to set an example for young people.

“Never give up when your day seems dim, never give up,” he said. “I will always run to help people. I don’t look at the office itself. I look at the situation that I’m running for people to serve and whenever that time comes, I still run because I run with the intention of helping others.”

NewsBen Garbarek