Terrence Wilson knows what it’s like to not have a home.
He made up his mind on a Tuesday five years ago to move to Chicago and, without money for lodging, he stepped off the bus at Union Station on a Sunday.
He said he told himself at the time: No more procrastinating. He “just had to make it happen.”
But making it happen took a little longer than anticipated, he said Monday, and he spent his first three months in a shelter on the North Side with 76 other men.
Over the years, he built a life for himself in the city, got a job and an apartment. Since September, he’s been a bartender at Petterino’s restaurant in the Loop. But he never forgot his time in the shelter — and he has been determined ever since to give back to Chicagoans in situations he experienced.
“It was one of those things that my mother instilled in me a long time ago,” Wilson said. “There are people who need, and when I think of how blessed I’ve been throughout my life — even in situations where I may have been homeless or was hungry or whatever — somehow, some way I was still cared for and I was still provided for, and therefore I know that the same has to be true for everyone else.”
Wilson, 50, made it his mission to help people without housing through his nonprofit, Chicago Life Cares. One-third of his paycheck goes to buying food, toiletries and other necessities for people who need them throughout the city. If he passes an encampment on his way to or from work, he takes note of its location and makes a point to drop off food before the day is done, be it downtown, along the Red Line, or in Rogers Park.
And he’s about to pull off his biggest giveaway yet.
On Christmas, Wilson and more than a dozen of his Petterino’s co-workers will serve 500 hot meals and give out care packages with coats, hats, gloves, emergency blankets and other supplies at the restaurant. While the Flint, Michigan, native has largely been a one-man operation, folks at the Theatre District restaurant were immediately on board to help, said Gary Fassl, director of restaurant operations for Petterino’s umbrella group, Good Plate Hospitality.
“Have we done anything like this in the past? We have not,” Fassl said. “But to be honest with you, we haven’t worked with someone like Terrence.”
Wilson estimates he has been giving out just under 100 meals each month. He cooks the food in his South Shore home, loads it into a massive suitcase — as many as 30 packaged meals at a time — and takes to the streets. Using public transportation (since he doesn’t have a car), he checks his Ventra app to see what’s closest.
“I run into people right there on the train, because, as we know, the Red Line is literally home for a lot of people, where they sleep,” Wilson said.
Wilson credits his giving nature to his late mother, Billie Jean Jamison. As she raised six children and two nieces, he said, she always found time to make sure they remembered they were loved.
“Once I was the only child at home, we stopped doing the big holiday dinners, and (my mom and I) began to attend an inner-city church that had a homeless shelter set up as well,” Wilson said. “We would spend our holidays there, fellowshipping with everyone from the community and helping to serve, make food, and sitting down and eating … that’s really where it began.”
He started his ministry from the trunk of his car while living in North Carolina in 2010. By 2020, the nonprofit became Chicago Life Cares, and Wilson had become a Christian minister. While he has yet to find a physical home for his church, most of his ministry happens in person or through social media.
“Passions run deep within me,” he said. “I continue to live based off of my emotions and my passion, and that’s what keeps me going every single day.”
But he still feels like he isn’t doing enough, he said. He has plans to open a food truck with his brother in the spring, with a buy-one-give-one format for paying customers that will fund free and healthy meals for people in need — a model he hopes could be replicated in other cities.
To make that happen, he’s splitting his workweek between bartending at Petterino’s and managing the convivial Italian restaurant. When he mentioned his fundraising efforts for Christmas meals — he gave out about 200 on his own for Thanksgiving — owners and co-workers were eager to lend a hand. Already, 16 volunteers have agreed to help out on Christmas Day, and the restaurant also donated to the cause.
“Terrence is one of those employees, and it’s a short list throughout my career, of people that stand out,” Fassl said. “Terrence has a huge heart and cares about other people, his co-workers, guests and he’s extremely easy to work with, which isn’t always common. He’s definitely a joy to be around. And there’s not a person at that restaurant that would tell you otherwise.”
And while the season of giving may be over for some on Dec. 26, the spirit of Christmas shines brightly through Wilson all year long.
“There are empty buildings in this city, and they should be filled with people,” he said. “Since they’re not, I’m going to make sure that people that are out here, know that they’re loved, know that they’re cared about and have the basic necessities. That’s my motivation every single day … the possibility of me being able to touch someone’s life in a positive way.”
Chicago Life Cares will be giving out meals and care packages at Petterino’s (150 N. Dearborn St.) from 2-5 p.m. Sunday. To donate, visit the nonprofit’s Facebook page, or via Cash App to $ChicagoLifeCares.
Big screen or home stream, takeout or dine-in, Tribune writers are here to steer you toward your next great experience. Sign up for your free weekly Eat. Watch. Do. newsletter here.