Sharecropper’s son turned successful businessman, Wilson wants ‘equal opportunity for all’

On the 46th floor of a penthouse condo overlooking Lake Michigan, Willie Wilson, his wife and a cadre of supporters mill about, all smiles, following what they deem a triumphant speech before the City Club of Chicago.

In the pristine front room hangs a historic photo showing “colored” bathrooms for African-Americans, as a reminder, Wilson says, of the era from which he came.

There’s also a framed inspirational collage that reads “The American Dream” where three African-Americans are pictured; two iconic leaders, Martin Luther King and President Barack Obama.

The third person? Willie Wilson.

Born the son of a Louisiana sharecropper, Wilson says he worked tirelessly to turn his life around. He eventually owned five McDonald’s franchises, started a medical-supply company and an Emmy-winning Gospel TV show. By his own estimate, he gives away up to $1 million a year to churches and charities.

Now, Wilson said he’s ready for the next challenge: Chicago Mayor.

Wilson is a political unknown, but his sizable self-contributions — beginning with $1 million in January — have garnered him attention. Aside from Mayor Rahm Emanuel, Wilson is the only other candidate in the Feb. 24 mayor’s race who is up with television advertising. 
He’s uniquely positioned to take on this task, he says, having built his own fortune from nothing.

Wilson said he knows what it’s like to struggle, what it’s like to succeed and how to bring together the people who are on the two ends of that spectrum.

Wilson is quick to talk about race, repeatedly saying Chicago remains too segregated, and he believes he can change that.

“One of the reasons I’m running for mayor, I think there is too much segregation in the city of Chicago. I think a lot of the segregation will disappear if we get money in people’s pockets. Equal opportunity for all,” Wilson said. “You be fair. You make sure you get legislation passed to make sure there’s equal opportunity.”

Wilson has a pretty important friend in Springfield – Gov. Bruce Rauner.

“Talked to him this morning,” says Wilson, who explains that Rauner called him to catch up.

Wilson endorsed Rauner in the governor’s race, specifically hoping Rauner would make good on implementing “right-to-work” laws or “empowerment zones” in economically depressed areas on the city’s West and South sides. The zones designate areas where unions are prevented from making membership automatic.

Wilson expressed frustration at seeing a lack of minorities doing construction work in minority neighborhoods.

“You go into the neighborhood. You see who are doing the construction, who’s driving that big machinery. Into the African-American community, all right,” said Wilson. “You look at the money that is paid. You’ll see the money is not getting back into those urban areas, into the minority areas. That’s a problem. Because now you’ve created an environment that’s worse, and you expect people to act right?”

“You’ve got some black who are also union as well . . . but I challenge the black people in the union one thing: Don’t support the unions that [are] discriminatory, that don’t have equal opportunity.”

In an era of tightly scripted politicians, a relaxed Wilson lets it hang loose, declaring he has no pretenses. Tells it like it is.

As evidence, he points to his self-published autobiography, “What Shall I Do Next When I Don’t Know Next What To Do?” which is filled with unflattering details of messy relationships and personal setbacks. In the book, he admits to having children out of wedlock and striking an ex-wife.
 He also discloses that one of his sons, Omar, was killed after being drawn into a life involving drugs and gangs.

It’s then with some irony that a public-relations crisis that hits the campaign later that day points directly back at Wilson.

The Chicago Sun-Times published a story online about Wilson’s City Club speech. “To the whiteys here, I’m letting you know, I ain’t prejudiced,” he said at one point to a welcoming crowd who laughed and applauded easily throughout his remarks.

The campaign insisted Wilson did not use the term “whiteys,” and Wilson himself later told the Sun-Times he would never use the term, saying it was akin to someone calling him “the n-word.”

When other media began reporting it, Wilson then said: “If I used the term ‘whiteys’ it doesn’t reflect my values.”

Two days into the story, his campaign offered up another explanation.

“When you slow it down it’s: ‘to da whites that is here,’” said a campaign aide, Greg Livingston. “That’s his broken country brogue. . . . He just doesn’t have the advantage of speech therapy where he came from.”

Throughout the mini-scandal, Wilson insists he’s looking to create more opportunities for whites and blacks alike.

“I think whether you’re white or black, you can’t argue against fairness,” he says.

Wilson would expand African-American hiring in City Hall and other departments so that it is modeled after the city’s population – 32 percent black, he said. He would do the same with giving out contracts to minority-owned firms, he said.

Wilson admits he’s far from polished. Last week he said he wanted to bone up for that night’s debate after feeling under-prepared at a televised debate the night before.

His lack of political experience isn’t a negative, he says.

“Rahm’s got all the political experience in the world, what does he do? He sells the city out. I got no political experience at all, what did I do? I give away my money to the community to help it,” Wilson said.

Wilson is legendary in the city’s black community for his philanthropy, easily handing out $100 bills to strangers in need. Wilson said he’s lowered his car window and given up to $1,000 to someone begging on the street.

There’s a taste of the dynamic between a too-loose-talking candidate and cautious campaign handlers in this interview.

At one point, Wilson is asked what he thinks about the Chicago Teachers Union and the CTU teachers strike.

“The teachers union really don’t impress me,” Wilson said. “I think the teachers should have been striking against their own union. Because they don’t have equal opportunity. The contract . . . the jobs . . . is not reflective of the employees who represent 400,000 students. . . . Maybe they should strike against themselves first. Get that together. Get that in order first.”

Wilson’s spokeswoman later interjects that the businessman strongly supports CTU and teachers, and didn’t mean anything negative by his comments that it should strike against itself. Wilson made clear that it was the city violence, along with the closing of 50 schools that spurred him into running for mayor. He called the move disrespectful to the communities affected.

“I said enough is enough when he closed those 50 schools,” Wilson said.

Wilson is evasive when asked how much he’s worth, whether he would describe himself as a millionaire or a multimillionaire.

“If Chicago don’t have money itself, I’m right there with them,” Wilson responded. Reminded that he, unlike most Chicagoans, was sitting inside his posh 46th floor condo overlooking Lake Michigan, Wilson said: “Let’s put it this way. I give away probably $800,000 or $1 million [a year] to churches.”

He then hands over a list of churches with dollar amounts beside them.

One of his staffers snatches it, saying they would provide a “clean copy” over many protestations by Wilson, who insists it’s fine to just release.

In the interview, Wilson, who boasts of donating millions of dollars to charity, initially said he would release his income taxes. Then he countered by suggesting candidates should release what they donate to the community.

Wilson’s is an incredible rags-to-riches story that by now, those paying attention to the mayor’s race know well.

The 66-year-old was born the son of a Louisiana sharecropper and spent some of his early childhood picking cotton. He eventually landed a job mopping floors at McDonald’s but dreamed of owning his own franchise.

That became reality after he showed up at meeting where McDonald’s founder Ray Kroc attended. Wilson told Kroc he was willing to work hard and asked for his help. According to Wilson’s book, Kroc helped make it happen. Wilson eventually owned five franchises, which he later sold.

He’s still involved in Omar Medical Supply, which in 2001 won a contract to provide plastic gloves to the U.S. Postal Service in the wake of the Anthrax scare. Wilson, then CEO, filed suit against the government claiming he was unfairly cut out of future contracts. The complaint was later dismissed, court records show.

In 1989, Wilson founded “Singsation,” a weekly Gospel music show thats airs on WGN. Wilson dons black tie and takes turns at the microphone, along with other talent. In 2012, Wilson won an Emmy for best performing artist. Wilson also once sang with the Gospel group “The Norfleet Brothers.”

He attained only a 7th grade education, but his supporters call him “doctor” for earning a series of honorary degrees. In an interview with the Sun-Times, Wilson says he has a B.A.— defining it as “Born Again.”

Wilson’s honorary degrees include a doctor of divinity degree from Mt. Carmel theological seminary, a doctorate in humane letters from Chicago Baptist Institute and a doctorate in humanitarianism from Swisher Bible College.

His wife points to her husband’s faith as a defining attribute, one that initially drew the two together.

Janette Wilson said she was at the Christ Temple Baptist Church in south suburban Markham when she first met Willie Wilson, who was a deacon, about 18 years ago.

She said she attended church each week, rain, sleet or snow, gaining a nickname from the pastor as his “faithful one.”

One day she decided she should go up and formally introduce herself to the pastor.

“As I went to shake his hand, Willie saw me and just grabbed me and touched me . . . on the back and said: ‘Are you a model?’ I said, ‘No, just a hard-working lady.”

She held two jobs in part to pay off debt she said her ex-husband had incurred.

“The other job was to live off of,” she said.

Mrs. Wilson has worked in the Cook County Comptroller’s office for 23 years, she said.

Janette Wilson tears up when asked to describe why her husband is suited to be mayor.

“He’s always been a lover of people, and passionate about people’s needs. I think because he grew up poor, he always had compassion,” she said. “He’s fair. He’s always been fair in business and in life. This isn’t something that’s just happening. It’s been in him.”