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Englewood, Chatham, Auburn Gresham

Why These South Side Women Voted For Willie Wilson — And Think You Should Have Done The Same

"The ballot was like a huge menu at a restaurant that you don't want anything from, but you have to order anyway."

Friends Deleen, Sandy, and Teonda are unapologetic Wilson supporters.
Jamie Nesbitt Golden/Block Club Chicago
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CHATHAM — On Tuesday, businessman and perennial candidate Willie Wilson had his best Election Day yet.

In 2015 when he ran for mayor, he got 50,960 votes. When he ran for president in 2016, he snagged 22,000 votes in the Democratic primary.

On Tuesday, in his latest attempt to become Chicago mayor, the self-made millionaire again fell short, coming in fourth behind Lori Lightfoot, Toni Preckwinkle and Bill Daley.

But he did manage to get 57,713 votes, largely from the South and West sides.

Credit: City Bureau
The green areas are where Wilson got the majority of votes in Tuesday’s election.

Wilson may be known for quirky soundbites and handing out $100 bills, but he’s also known for being present and accessible in the community, and not just during election season.

It’s that accessibility — and no nonsense approach — that made LaDonna Blair cast her vote for him.

Blair, 42, is from Washington Heights, where a lot of the older folks she spoke with prior to the election had already decided to vote for Wilson. At the beginning of the race, she considered voting for political newcomer Amara Eniya.

“She was my first choice but I felt she didn’t stand a chance,” said Blair. “The ballot was like a huge menu at a restaurant that you don’t want anything from, but you have to order anyway.”

“When it came down to the wire, like me standing at the voting booth, I had to make a choice.”

The one thing she noticed at her polling place was the absence of younger voters, which she found disappointing. But it’s the older black folks who vote, said Blair.

“That’s all I saw at my polling place. Many had expressed interest in Willie Wilson,” said Blair. “I damn sure didn’t want to hand the keys over to Daley, Lightfoot or Preckwinkle.”

A trio of friends — older black women sharing breakfast Wednesday morning at Josephine’s Cooking/ Captain Hard Times at 436 East 79th Street — agreed that Wilson was the best choice.

Sandy, Deleen, and Teonda (who asked to have their last names withheld) have been friends for decades and regulars at the restaurant. Deleen, who lives in the suburbs, worked on Wilson’s campaign because of his compassion and vision.

“I liked that he was concerned about those who had the least,” Deleen said. “He cares about helping the youth, and reaching out to people. He’s hands-on.”

“He’s a self-made millionaire,” chimed in Sandy, pointed to his several McDonald’s franchises as proof of his business acumen. “But the younger, educated black folks won’t vote for him because of how he talks. It’s ridiculous.”

Deleen blamed Wilson’s campaign handlers for making him more of a spectacle than a serious candidate.

“It wasn’t structured and there were too many distractions,” added Sandy. “They kept him busy with press conferences and the press took his soundbites and tried to make him look like a fool. His people should’ve focused more on getting him out there in the community.”

“A lot of people don’t understand how politics work. People tend to vote for those they have a relationship with.”

While not fully onboard with either candidate currently in the runoff, the trio of friends said they could work with a Preckwinkle win.

“She may not be personable, but she’s effective. She could bring resources to the table,” Teonda said. “I’m not sure if Lightfoot could do that. She barely comes to the South Side to talk to us.”

“If the younger black people had come out and voted last night, Wilson would’ve won,” Sandy said. “He needs those voters.”

For more neighborhood-level election maps, check out City Bureau’s here.