Skip to content

Giveaways aren’t new for Willie Wilson

By Sidney Madden | @sidney_madden_


Self-made millionaire Willie Wilson is set to give out free gas again Thursday after last week’s turbulent $200,000 giveaway that resulted in traffic jams citywide. But this time, the business owner is doling out $1 million of gas

Whether you thought it was a savvy move like Chicago Sun-Times’ Laura Washington or a harmful one like Streetsblog Chicago’s John Greenfield, the giveaways are definitely on brand for Wilson.

Cars from down the street are trying to get into a crowded gas station. The gas station sign has prices ranging from $4.49 to $5.49.
Gas giveaway in Humboldt Park Thursday. (Scott Olson/Getty Images)

Wilson has long handed out cash to Chicagoans, from regularly giving checks to churchgoers to pledging $1 million to unemployed people at the beginning of the pandemic. 

But given his various political endeavors, many have questioned his motives. 

The 73-year-old has self-funded unsuccessful runs for mayor, president, mayor again, and U.S. senator in the last decade.

But don’t overlook Wilson’s political capital in Chicago. Politicians have cozied up to the entrepreneur for his influence in the city’s Black community, according to Chicago magazine: 

  • Former Gov. Bruce Rauner put Wilson on his transition team in 2014.
  • Wilson’s endorsement of then–mayoral candidate Chuy García had incumbent Rahm Emanuel scared in 2015.
  • Mayor Lori Lightfoot and Cook County Board President Toni Preckwinkle vied for Wilson’s endorsement in the 2019 mayoral race. 

As the son of a Louisiana sharecropper, Wilson came to Chicago at age 13 without having finished seventh grade. He got a job at McDonald’s, became a manager, and later franchised five locations. He’s since made a fortune with his company Omar Medical Supplies, and has run the nationally syndicated gospel show “Singsation” for decades. 

The entrepreneur’s philanthropy has been controversial before: He was accused of breaking campaign finance laws by not disclosing his cash handouts during his second mayoral bid, WGN reported. 

No matter how you feel about Wilson, you can get free gas at 50 locations across the city and county courtesy of the longtime entrepreneur Thursday starting at 7 a.m.


Chicago attorney Jay Edelson filed a lawsuit in 2015 against the social media giant claiming it violated his client’s privacy, specifically Illinois’ biometric privacy law, one of the strictest in the country. 

Facebook settled the class-action lawsuit in February 2021 for $650 million, and the settlement was upheld in a court of appeals late last week. That means eligible Illinois residents could get a $397 check from Facebook in the next 60 days. 

🎧 Edelson explains the lawsuit, and how privacy laws continue to change.


1. City Cast readers and listeners are involved in their communities AND actively exploring and learning about other neighborhoods.

2. They’re trying new restaurants but aren’t snobby about it.

3. They have good taste — clearly 🙃

Check out our advertising options, or email


▪️ Gov. JB Pritzker said the state continues to build its supply of COVID-19 tests and vaccines as the BA.2 variant spreads across Europe. The more contagious omicron sub-variant makes up 25% of the state’s cases. [Block Club Chicago]

▪️ Blue Cross Blue Shield of Illinois’ parent company is being fined $339,000 for violating the state’s transparency act. [Capitol Fax]

▪️ CPS’ proposed calendar for the 2022-23 school year is out. The Board of Education will vote on an Aug. 22 start date Wednesday. [ABC7]

▪️ A public viewing for WVON’s Pervis Spann is happening in Grand Crossing today, and a wake and funeral is planned in Woodlawn Wednesday. The iconic DJ died last week. [Chicago Sun-Times]

▪️ A new report details a reimagined Magnificent Mile. [Crain’s Chicago]

▪️ Eat your way through the best slices of cake in Chi 🤤 [Eater Chicago]


Two years ago at this time, City Cast reader and actor Nick was halfway through a run of a show in the northern burbs when things started to shut down.

“Small theater space, close contact with audiences and castmates, and even a stage kiss between me and another actor. Yikes. As a cast, we decided it was unsafe to continue, so we shut down the production. Turns out it was a good decision.”

Tell us about the last normal thing you did before COVID shutdowns two years ago. Email or text/call (773) 780-0246.

Not subscribed yet? Fix that 👇

Group 12 Copy 2