Long before Craig Wilson put on a red suit and climbed into a three-wheeled Polaris Slingshot, generosity was already part of his identity. Wilson, known across the southland as “Slingshot Santa,” grew up watching his parents quietly feed neighbors, create jobs, and help anyone who showed up at their door.
His mother, Sherrie, “never gave up on anyone,” Wilson said. His childhood home, located on the corner of 165th Street and Winchester, became a gathering place for anyone in need of a meal, advice, or simply a place to feel seen. His father, a businessman, offered second chances by providing employment opportunities. Between the two of them, Wilson said, giving was “just what you did.”
That legacy became the foundation for Sherrie's Corner; the nonprofit Wilson created in his mother’s memory after her death three years ago. The organization, named for both the woman and the literal corner where so many acts of compassion took place, focuses on “where hope and humanity meet.” It now supports a wide array of community needs — from education and housing resources to mental health awareness, nutrition classes, and tools to help families gain stability.
Slingshot Santa is its most visible extension. What started nine years ago with 85 toys wrapped in Wilson’s garage has grown into a large-scale holiday effort supported by corporate sponsors and Toys for Tots. Last year alone, the organization distributed more than 2,300 toys throughout the entire month of December to children and families across the south suburbs — not just on Christmas Eve and not just at Walgreens.
Still, the Christmas Eve stop at the Walgreens in Olympia Fields, located on Governors Highway, has become one of the most recognizable parts of the tradition. Wilson remembers an older woman who came through the store one year looking defeated. He offered her a hug and a gift card sealed inside a Christmas card. She returned moments later, emotional, explaining she had just lost both her husband and son. The unexpected kindness, she told him, was the first light she’d felt in weeks.
Moments like that, Wilson said, are why he bundles up every Christmas Eve — no matter the snow or cold — and brings his slingshot out again.
By day, Wilson has spent 25 years with U-Haul. At home, he’s a husband, father of four, and grandfather of four. His wife, Linda Wilson, a retired educator, has long supported both his ministry and his community work. He’s also a minister himself, committed to “faith, hope, and charity” beyond the holiday season.
And while he’s known to appear at various locations throughout the region — including Walmart, Walgreens, and community events — being part of Park Forest’s annual Holiday Market celebration holds special meaning. It’s home.
“You’re subject to seeing me anywhere,” Wilson said, laughing, but being embraced by his own community is something different. The police and fire escort, the families gathered in the Village Green — to Wilson, those moments reflect exactly what his parents taught him: take care of home first, and the rest will follow.
For Wilson, Slingshot Santa isn’t a costume or a title. It’s a promise to keep spreading joy, one unexpected act of kindness at a time. You can see Slingshot Santa, this Saturday on the Village Green at 11 a.m.