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Sheila and Chris Kennedy


Running Together

By Laura Hine

Portrait by Lucy Hewett | Shot at the Knoll Chicago showroom, Merchandise Mart


Sheila and Chris Kennedy have made his run for governor an all-hands-on-deck family project, which is not surprising: Family is what they do best.

THEIR INTRODUCTION SOUNDS like a movie meet-cute. Chris Kennedy was driving across the campus of Boston College, where he and his cousin were students. “He saw his cousin and told me to slow down.” Chris recounts. “I stopped, and Sheila came over to the car. She kissed hello to her cousin, who is also my cousin.

“We’re not cousins, but we have mutual first cousins,” Sheila says, trying to explain the complicated Kennedy family tree. After the introduction and figuring out their family connections, “I knew that I would marry her,” Chris says.

He was right. The couple just celebrated their 30th wedding anniversary, and they’ve raised four terrific kids in Kenilworth, where they’ve lived for the last 25 years. Chris was president of the Merchandise Mart for 10 years, and when he left, the couple started Top Box Foods, a nonprofit hunger-relief organization where Sheila is the executive director. Chris also chairs the Kennedy family’s investment firm. So they’re busy, and about to get busier. Chris is running for governor of Illinois, and as suits this close-knit clan, the whole family is involved.

“When it was time to make the decision to run, everybody was in 100 percent, but it took me a little bit more time to catch up because politics can be so mean-spirited and nasty,” Sheila says. “But given what I think of Chris—and I believe he has the skills and temperament to be an excellent governor—I just thought it was time for me to be brave.” As we talked, Chris explained his reasons for running, which go back to the importance of family. “There’s a whole class at New Trier that wants to move away, and unless we change the direction of the state, that’s the outcome. Our kids will live somewhere else.” For a family whose children went to school with cousins and second cousins, the thought of families dispersing and leaving Illinois is reason enough to put it all on the line and run—together.