How Willie Wilson changed his mind on LGBTQ people and endorsed Lori Lightfoot

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Willie Wilson endorses mayoral candidate Lori Lightfoot at a press conference at Chicago Baptist Institute International. | Ashlee Rezin/Sun-Times

Back in December I wrote that businessman Willie Wilson “had a long way to go” to win over LGBTQ voters in his mayoral campaign.

Today, Wilson has arrived, at least symbolically, with his endorsement of former Police Board President Lori Lightfoot in the April 2 mayoral runoff.

Wilson, 70, is a Southern-born businessman and devout product of the socially conservative black church. He is a true believer in the Bible, in scripture that says homosexuality is a sin.


Yet he has heartily embraced Lightfoot, 56, an African-American lesbian, who is raising a daughter with her white spouse.

Lightfoot and Cook County Board President Toni Preckwinkle had been pursuing Wilson’s endorsement since they made the runoff. Wilson didn’t make it, but he won 10 percent of the vote in the Feb. 26 election, mostly from 13 wards on the south and west sides.

Wilson’s voters are likely older, church-going African-Americans who cheered him for decades of charity to the needy, and for his straight talking on fairness and equity. Wilson’s support of Lightfoot defies the homophobia that plagues the black church. His personal journey shows how far Lightfoot — and Chicago — can go.

During his 2016 run for president, Wilson tweeted: “I disagree with what I consider the Supreme Court’s reinterpretation of what constitutes marriage. Marriage has and should always be that sacred union between a man and a woman. Period.”

I reminded him of that as we chatted at a holiday reception he hosted for the LGBTQ community, his first effort to “reach out.” He mangled the “LGBTQ” acronym. I explained the difference between Boys Town and Andersonville.

“By reaching out, we all can learn,” he said.

Wilson learned. He campaigned at the gay bars along North Halsted Street. He hired LGBTQ staff.

On Thursday, Wilson shared his deliberations over the endorsement in a phone interview.

There were meetings and calls with at least 300 ministers and community leaders, he estimated. An online poll of his supporters leaned heavily to Lightfoot. But Wilson also got pushback on Lightfoot’s sexual orientation. “It’s a major problem,” he said. “People are calling my voice mail and talking about scripture.’’

And, “I used to think the same way.” Now, he says, “Let Christ do the judging. Not me.”

Now, it’s not about sexual orientation. “It’s about the economy.  Fairly and equally distributed jobs in City Hall that reflect the people who voted for me.”

Wilson added: “What we are trying to do here (is) create jobs, get contracts and economic associations. Even the playing field.” He met with Lightfoot three times and decided she could best carry out that mission.

At Friday’s announcement, Wilson and Lightfoot stepped up to the podium, flanked by about 50 ministers and community leaders. He began, as always, with prayer. “Thank the Lord, his amazing grace.”

It’s “time for a change,” he declared, and urged his voters to turn out for Lightfoot. “I’ll be right by her side.”

His nod may help Lightfoot win. It may not.

Willie Wilson has evolved from a deeply religious man whose cherished beliefs were hostile to gays; to a man who courted their votes; to a man who could help elect the city’s first LGBTQ mayor.

Chicago has already won.

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