From Courtroom to Court Side

  • Majority owner of the Maine Red Claws, Bill Ryan, in the stands at the Portland Expo.

Trained as an attorney, Maine Red Claws owner Bill Ryan finds his passion in sports.

Having a conversation with Bill Ryan is like moving a basketball down the court during a game of hoops. William J. Ryan, Jr., easily engages with whatever topic is passed in his direction— from racing cars to raising children—and returns the favor by sending questions of his own across the table. With the build of a former college athlete, and the analytical mind of an attorney, the principal owner and chairman of the Maine Red Claws is a skilled communicator. “I will listen to almost anyone if they have something to say,” says Ryan. “Even if I don’t agree with them, I usually learn something.”

This trait has come in handy for a man whose broad range of experiences includes co-hosting Maine’s only live motorsports radio talk show, serving as a trustee for the Portland Museum of Art, and owning the Oxford Plains Speedway. “My natural inclination is to care about the people around me and what their lives are,” says Ryan, who is also an advisory board member for the Harold Alfond Institute for Business Innovation at Thomas College in Waterville.

Ryan was born in New York, and grew up in Topsfield, Massachusetts—a town whose claim to fame, he says, is having the oldest agricultural fair in the United States. As the oldest of four children, and only son, he and his father bonded over watching professional basketball. “My father is a maniacal fan of the Celtics,” says Ryan, who played the sport (as well as baseball and football) at Masconomet Regional High School in Boxford. He went on to play two years of football at Williams College in Williamstown, Massachusetts, before sustaining a knee injury that ended his athletic endeavors. 

A political science major at Williams, Ryan didn’t have a specific plan for his future. “My parents kept calling me and saying, ‘What are you going to do with your life?’ One day they woke me up and I said, ‘I’m going to be a lawyer.’ That got approval—they didn’t bother me for the rest of my senior year.” Ryan received his law degree from Suffolk University in Boston, and followed his parents to Maine, where he worked for Verrill Dana in Portland. “I liked law school, then when I got out, I found out what lawyers actually did,” he says. In the meantime, he and his wife Stacey (his high school sweetheart) started their family. They had four children—son Will and daughters Molly, Kate, and Abby—in five years. “I needed a job, so I stuck with it until I could figure out what else to do,” says Ryan. “It’s good training for business. It’s great for some people; it just wasn’t for me.”

After spending several years working for a sports marketing firm in Boston, Ryan learned that Oxford Plains Speedway in Oxford needed a new owner. “I became fascinated with the [car] racing business,” says Ryan. “It wasn’t anything I really knew about.” He bought the 3/8-mile racetrack and took on the challenge of attracting fans to the western Maine venue. The weather proved to be an important factor. “If you have 40 events scheduled for summer and it rains three weekends in a row, you could lose 10 percent of your opportunity to make money for the year,” says Ryan. “It’s like a retail store that’s open 365 days losing 36 days, where they make zero money.”

Ryan found that being at the racetrack for 14 years gave him a deeper understanding of the Maine community. “There’s a wide demographic for racing. I could talk to anybody,” says Ryan. “I still bump into people all the time that I know from racing, who are from all walks of life.”

While he still owned Oxford Plains, someone who had worked for the Boston Celtics many years before contacted Ryan about creating a professional minor league basketball team in Maine—one that would be part of the NBA development program. At first Ryan was skeptical (especially given that two professional basketball teams had previously failed in the state), but he spoke with his father about the opportunity and soon became convinced that the idea had merit. Part of the planning process involved bringing league officials to Portland. Then-governor John Baldacci agreed to participate in this visit. “One official later told us that they had never had a governor do this before. That was probably what got us the franchise,” says Ryan. “That’s the way the state of Maine is. You can call the governor and they will work with you.”

Ryan and his father, William J. Ryan, Sr., (former CEO of TD Bank in Maine) formed a group of investors and became majority owners of the Maine Red Claws. The team, which is affiliated with the Celtics and plays its games at the Portland Expo, is now in its ninth season. “It’s a community in a lot of good ways,” says Ryan. “You have that universal language that you can talk about, like, ‘Did you see that game last night? What do you think of the Celtics?’”

After many years living in Falmouth, Ryan and his wife moved to Portland’s West End last year, after their youngest child left for college. “I feel strongly that I want them to be able to support themselves, but have fun and enjoy what they’re doing,” says Ryan, remembering the daily headaches and unhappiness he experienced while working as a lawyer. While recognizing the importance of running a sustainable business, Ryan has a philosophical take on what it means to be successful. “As you get older, and you get a little bit wiser, you realize that if the Red Claws lose tonight you’re still going to be here tomorrow,” says Ryan. “It’s not life and death. We’re not curing cancer. We’re just hopefully giving people a night out where they can smile and laugh and have fun and watch a good game.”


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