
Chris Kennedy has called Illinois his home for three decades and reveals why he’s here to stay. PHOTOGRAPHY BY FRANK ISHMAN
The Kennedy family is indelibly associated with Boston and Washington, D.C., but Chris Kennedy—the eighth of the late Senator Robert F. Kennedy and Ethel Skakel Kennedy’s 11 children—has lived in Illinois for three decades. Kennedy’s journey from the East Coast to the Midwest started with a post-college move to Decatur, Illinois to work for Archer Daniels Midland after graduating from Boston College in 1986. Not incidentally, his college sweetheart, Sheila, was also bound for her native Illinois with plans to attend Northwestern University’s School of Law. After marrying, the couple settled into a downtown Chicago apartment and began their family.
Twenty-two years ago, after the birth of the second of their four children, the Kennedys left the city for the North Shore. The family moved to Kenilworth because of the strong school system and proximity to much of Sheila’s family, including her sister and her four children, her brother and his four children, her 20 first cousins, and her parents. “I have a large Irish-Catholic family like the Kennedys although, with the exception of my parents, the majority are Republican,” she explains with a dry understatement.
“We can’t go get a cup of coffee or visit The Book Stall without running into one of Sheila’s grade school or high school friends,” Kennedy says. “We wanted that for our children. Here the neighbors know each other, and the kids can walk to each other’s houses.” Favorite activities for the couple include running along the lakefront in Gilson Park, biking along the Sheridan Road bike path, and attending concerts at the Ravinia Festival in Highland Park.
There was no one moment when Kennedy realized Illinois was home. “It happened incrementally,” he recalls. “But there was a point where Art Chicago (the international art exhibition that began its life at Navy Pier) was in trouble and we were asked at the Merchandise Mart if we could help. The carpenters, the electricians, and the plumbers worked 35-40 hours straight. Cultural institutions came together to help us. So many people worked together, worked hard, and accomplished something extraordinary. I knew I would never leave. I wanted to be around all those people.”

Chris Kennedy with his parents Robert and Ethel Kennedy and his siblings circa 1965
The Kennedy family’s twin traditions of public and community service were instilled in Kennedy and his siblings as “the product of thousands of conversations and teachable moments.” Kennedy recalls a lot of discipline and rules. “Dinner was at 7 p.m., and nobody was late, ever,” he remembers with a smile. “My mother would make us recite poetry every Sunday night at dinner. With my older siblings having already been doing it, it seemed natural that that’s what we would do. That order and routine is a source of strength for all of us.” There was also a lot of leading by example. “We saw our mother was very compassionate towards other people and we understood that’s how we should be as well,” Kennedy explains. “We saw my brother Joe start Citizens Energy and recognized we needed to incorporate service as a part of our lives. We saw family members run for office and knew that if we were confronted with bad governmental behavior, we were obligated to do something about it too.”
Chris and Sheila have instilled a strong sense of service in their own children, Kate, Chris, Jr., Sarah, and Clare. “New Trier High School provided great opportunities for the kids,” Kennedy says. “All four coached Special Olympics there. They also took advantage of opportunities to work alongside kids with developmental disabilities.”
Kate works in New York City at New Leaders, an organization that provides leadership training to educators. While at Boston College, Sarah was involved in Best Buddies International—a global volunteer movement that advocates for people with intellectual and developmental disabilities. Two of Chris and Sheila’s four children are involved in the family’s nonprofit, Top Box Foods, which provides access to healthy and affordable foods to families in “food deserts”—areas that lack grocery stores or have an abundance of fast food. Chris, Jr. started Middlebury Foods, a version of Top Box Foods, in Middlebury, Vermont. He now works in Evanston and volunteers with friends each month on one of Top Box Foods’ delivery routes. Clare, who is graduating from New Trier in June, is also a Top Box Foods volunteer.

Sheila and Chris Kennedy
Family discussions are commonplace on the North Shore. It’s just that in a Kennedy household those family discussions might involve a decision about whether or not to run for public office. “We talk about everything,” shares Sheila. “It’s no different than any other big decision. You weigh the pros and cons.” In this case the pros won; last February Kennedy announced his candidacy for Governor of Illinois. The discussion and the decision “did not shock anybody. My mother asked, ‘What took you so long?’ There was a lot of enthusiasm,” remembers Kennedy.
This is Kennedy’s first political campaign as a candidate. Up until now, Kennedy has personally eschewed politics for business. He served as chairman of the University of Illinois Board of Trustees from 2009 to 2015 and was president of the Merchandise Mart for 12 years. In 2012, Kennedy and Sheila founded Top Box Foods. As Kennedy is already making a positive difference every day in people’s lives, some might wonder why he would want to become mired in Springfield’s tumultuous political climate. Sheila, a third-generation Winnetka native, has the answer.
“Politics, as we know from the last presidential campaign, can be brutal. I’m 100 percent behind my husband,” she explains. “I work full-time but I attend the events and when I hear him speak and answer questions it reaffirms everything I believe about him. He can get the job done.”
For first-time candidates, name recognition can make or break their campaigns. Kennedy does not have that problem. The Kennedy moniker is considered by many to be the American equivalent of royalty. “They are an incredible family,” Sheila observes. “To a person they are open-hearted, and generous. Every single one of them believes in giving back and trying to do their best to make the world a better place. That’s how they live.”
When Kennedy was growing up, the family did not read books or see movies or TV shows about themselves because that would have been, as Kennedy describes, “self-referential.” On the campaign trail, however, Kennedy has grown accustomed to people’s eagerness to talk to him about their personal connection with his family. He enjoys hearing these stories. As “they are interesting to me and they will be interesting to my kids,” he has begun collecting and preserving these campaign trail stories on video.
Next year marks the 50th anniversary of his father’s assassination. Kennedy does have personal memories of him but they are private; he does not talk about them. Only four-years-old when his father died, Kennedy essentially had to learn about Robert Kennedy secondhand. Kennedy says a fact that most impressed him about his father was that Robert Kennedy—at 40-years-old and with no experience—was the first man to reach the summit of Mount Kennedy, the Canadian peak named in John F. Kennedy’s honor. A few years ago, Kennedy himself scaled this same peak.
Kennedy is, of course, no stranger to politics. He worked on his uncle Ted Kennedy’s presidential bid in the 1980s. He chaired Paul Vallas’ 2001 Illinois gubernatorial campaign. What Kennedy finds so different about the campaigns of today is how easily personal attacks can go viral via the Internet. “I think that shocks a lot of candidates,” he said. “The trick is not getting rattled by it.” Some pundits say Kennedy’s campaign is a referendum on the Kennedy name. “I wish it was,” he jokes. “But in the end, whatever happens, it’s on me.”