Christopher D. McCleary, ’91, was never pushed by his father, Thomas R. Roberts, ’66, toward any one career path. Instead, he was encouraged to discover and pursue what naturally interested him. The freedom to choose, it turned out, enabled McCleary to realize a genuine interest in the law and follow in his father’s footsteps as a Michigan Law alumnus.
“My dad never said anything to me about going to law school, but he was delighted when I told him I would be attending Michigan Law, as he did,” says McCleary.
Fast forward another three decades: McCleary’s daughter, Caroline—who was raised with the same open-ended encouragement—arrived as a 1L at Michigan Law in fall 2025.
“Caroline had pursued the STEM field as an undergraduate, so I never dreamed that she would think of law school,” he says. “She surprised me in the same way I seem to have surprised my dad.”
Taking a leap
As a double Wolverine, McCleary earned his undergraduate degree from the College of Literature, Science, and the Arts. He then worked for two years as a management consultant before returning to Ann Arbor for law school.
“Michigan Law, frankly, changed the way I think,” he says. “Being in a smaller environment learning alongside a number of people, who you’re going through this intense experience with, really allows you to create strong bonds. It was the most incredible time for me.”
McCleary joined a firm in San Francisco after graduation, where he helped establish its intellectual property litigation practice before transitioning to in-house work at Visa International Service Association. In 2015, he joined the United States Olympic and Paralympic Committee (USOPC) as general counsel. McCleary had been thinking about a change in career, and appreciated that the role allowed him to turn his favorite part of his previous work into his entire job, every day—while also working for a cause he believes in.
“Throughout my time as an IP lawyer, then advertising lawyer, then sponsorship lawyer, I was always at the edge of sports law,” he says. “I loved that part of my work the most; there is a real power to sport and the sacrifice and accomplishment of the people who become elite international Olympic and Paralympic athletes. I felt it was an incredible opportunity that came at the right time in my career.”
McCleary worked for the USOPC until his retirement in 2025, and he held leadership positions overseeing the legal, operations, and finance departments. “What I like doing best is helping other people succeed and do great work,” he says. “I also believe in bringing people onto your team who are smarter than you and helping them shine.”
Christopher D. McCleary, ’91Michigan Law, frankly, changed the way I think,” he says. “Being in a smaller environment learning alongside a number of people, who you’re going through this intense experience with, really allows you to create strong bonds. It was the most incredible time for me.
Paying it forward
Since retiring, McCleary has been teaching at the University of Washington School of Law as an adjunct professor and serving on the board of the Sports Lawyers Association (SLA). He has also remained connected to the Michigan Law community, most recently honoring his father through a gift to their shared alma mater that established a scholarship in his name.
“I think about what U-M did for my dad, who was a first-generation college graduate and went on to earn a legal degree,” says McCleary. “He was a GI Bill student who wanted to advance himself in ways that his family hadn’t thought of. I think about the jump he made, and then I think about what the same institution was able to do for me. I couldn’t be more grateful. That’s why it’s gratifying to be able to honor him through this scholarship.”
