Sam Kennedy ’95 leads the Boston Red Sox as president

By Mary Howard

On a winter morning in 1993, Sam Kennedy ’95 sat down at his Mac computer. It was a Saturday, 9:00 a.m., a time when most undergraduates are still asleep. But despite the hour, the American studies major had given himself an ambitious assignment: to write every owner and president of all 28 Major League Baseball teams. Kennedy was set on a career on the business side of baseball, and his letters requested advice and a summer internship. It was an ambitious move for the college sophomore and set him on a path that would lead to his current position as president of the Boston Red Sox.

“I have always had no doubt he would achieve his dream,” says Brendan Monahan ’95, Kennedy’s college roommate and lifelong friend, who witnessed the letter-writing marathon. “He has always been willing to work harder than anyone else.”

As president of one of the oldest baseball teams in the country, Kennedy works plenty hard. Managing a staff of approximately 300, he oversees all the team’s business matters, including ticketing, corporate sponsorship, broadcasting, marketing, advertising, and client services. He is also in charge of Fenway Enterprises, which handles all non-baseball activities at the park. But the workload doesn’t faze him. “When you love what you do, the last thing you think about is the hours.”

It is the love of the sport that fuels Kennedy. Despite his high-level position, at the end of the day, he is a baseball fan. “I never take for granted the opportunity to work in Major League Baseball,” he says. On his way to work each morning, he takes time to walk through the ballpark.

Growing up in Brookline, Massachusetts, just a mile from Fenway, he watched games perched on his father’s shoulders. An Episcopal priest, Kennedy’s father was eligible to receive $2 standing-room-only tickets as part of a clergy pass program. (After joining the Red Sox in 2002, Kennedy reinstated the pass.)

“Just to be out there with my dad and standing on his shoulders was awesome,” Kennedy told The Boston Globe in 2014. He estimates he attended 20 to 30 games a year with his family as a child. “This is the magic of baseball: it’s intergenerational.” Kennedy says his proudest moment with the Red Sox was on Father’s Day 2005, when he gave his 2004 World Series ring to his father.

It was baseball that brought Kennedy to Trinity. An ace player and captain of his high school team, he was recruited by then-Head Coach Bill Decker in 1991. “He came out to see me play and said he had a place for me,” says Kennedy, who applied to Trinity early decision.

But after a season with the Bantams, it was apparent to Kennedy that he didn’t have what it takes to succeed in college baseball. “I knew I needed to find another way to stay in the sport,” he says. So, he shifted his focus to the business side and launched his letter-writing campaign.

Those 56 letters garnered two responses, one from the Milwaukee Brewers and one from the chief operating officer of the New York Yankees. His allegiance to the Red Sox notwithstanding, Kennedy interviewed with the Yankees that spring and interned for them during the next two summers, working in ticketing and media relations. “Running between the clubhouse and the ticket office, I was in heaven,” he says.

He also took advantage of Trinity’s location to intern with the Hartford Whalers hockey team (now the Carolina Hurricanes) and the now-defunct Hartford Hellcats basketball team. “This opportunity to intern while I was at Trinity was hugely valuable to me. I was a recent college graduate with experience in three sports.”

Kennedy says the relationships he built at Trinity set the course for his life. “Whether meeting my wife, lifelong friends, professors, or administrators, I had the good fortune of choosing the absolute perfect college environment,” says Kennedy, who is a member of Trinity’s Board of Fellows.

After graduation, Kennedy had a brief stint selling advertising for sports radio before joining the San Diego Padres. As an account executive, he tripled his revenues and caught the attention of then-Padres president and CEO Larry Lucchino. When Lucchino acquired the Red Sox in 2002 (along with partners John Henry and Tom Werner) and became the team’s president, he brought Kennedy along.

From 2002 to 2015, Kennedy was instrumental in the revitalization of the Red Sox brand and securing the financial stability of the franchise. He and his staff dramatically increased the team’s revenue streams. Under his leadership, the Red Sox sold out 794 consecutive games at Fenway, beginning in 2003, establishing a Major League Baseball record.

In 2004, Kennedy helped found Fenway Sports Management, an international sports sales representation agency whose clients include NBA superstar LeBron James and the Liverpool Football Club.

He also led efforts to renovate and preserve Fenway, establishing it as a premier destination in New England for hockey and soccer games, corporate functions, and concerts. James Taylor and Billy Joel are on the roster for this summer.

Along the way, Lucchino became a mentor to Kennedy. “His role in my life has been a blessing,” he says. When Lucchino announced his retirement as team president last August, Kennedy was selected to take over. He officially began his new job on October 16, 2015.

“It is humbling in many ways,” says Kennedy about replacing his mentor. But as chief operating officer for the past six years, as well as Lucchino’s closest adviser, he expects a smooth transition. “It’s not a turnaround situation,” he says. “My principal job is to preserve and protect the foundation we have laid here.”

Talk to anyone who knows Kennedy, and they mention his drive. “I have always been impressed by Sam’s determination,” says his wife of 18 years, Amanda Johnson Kennedy ’94, a member of Trinity’s National Alumni Association Executive Committee. The two met at Trinity but got to know each other when Kennedy interned for the Yankees, as Amanda grew up on the Upper West Side. She credits his success to his gregarious personality, a strong sense of urgency, and his passion for baseball. Interestingly, Kennedy’s brother, James ’99, also married his college sweetheart, Tamara Wiley Kennedy ’97.

Jay Monahan ’93, brother of Kennedy’s college roommate Brendan, says his friend and Psi Upsilon brother is “the most driven and passionate person I know.” Now deputy commissioner of the PGA Tour, Monahan calls Kennedy his sounding board and mentor. “I couldn’t respect the man more,” he says.

Kennedy is a people person and says the most rewarding part of his job is being able to take care of others. “Whether it’s upgrading seats for a fan or creating resources for staff, it’s a real privilege,” he says.