Relationships & Championships, From Trinity to Fenway and Back

by Samuel H. Kennedy

Truth has a funny way of revealing itself. And the one thing for me that has held fast through the course of my life is that the personal relationships you form are what really matter. And when you truly recognize and cherish the value of those relationships, you create opportunities and establish a culture that allows miracles to happen—like, say, a Trinity College benchwarmer becoming the president and CEO of the Boston Red Sox.

Let me be clear: I am not talking about likes, selfies, swipes, and texts. I am talking about genuine authentic relationships, the kind of bonds that can change your life. So, am I saying I’ve discovered the secret of life? As Curly would say, that’s for you to figure out. But indulge me for a few minutes while I tell you how relationships have impacted my journey. And how human connections transformed a baseball team that had conditioned generations of New Englanders into believing that in the end, you’re going to have your hearts broken.


Taking a cue from my old Brookline High teammate, Theo Epstein, who had recently landed an internship with the Baltimore Orioles, I spent my sophomore year walking from Clemens to the computer science center, feverishly writing letters to major league clubs, seeking a summer internship.

I wrote nearly 100 letters to owners, presidents, and general managers of teams in search of an opportunity. Yes, good old-fashioned, typewritten letters, with stamps and all! But as quickly as those letters went out, the rejection letters came back, stuffing my mailbox at Mather. While this may sound discouraging, the thrill of receiving envelopes adorned with Major League Baseball logos was enough to keep me going. And then, on March 31, 1993, I received this: an offer letter—wait for it—yes, from the New York Yankees. For three summers I interned at Yankee Stadium, doing entry-level work. Evidently, they didn’t see me as the next Derek Jeter of the front office because when I graduated, there was no job waiting for me. So, I took a job selling radio advertising in Manhattan. I hated every minute of it.

By then, my childhood friend Theo had followed his boss, Larry Lucchino, west to San Diego, and he offered to put in a good word for me. Soon, I found myself working in sales for the Padres. And six years later, when Larry signed on with John Henry and Tom Werner in their successful bid to buy the Red Sox, the two kids from Brookline were on their way home.

I remember our dads telling us, “Be bold, guys. Don’t waste this opportunity.” We vowed to make a difference, and we worked 24/7 to prove it. And again, we saw the value of relationships. When the Minnesota Twins cut David Ortiz, his close friend Pedro Martinez got on the phone to us, urging that we sign him. The Legend of Big Papi was born. Then my close friend, my Psi U brother Jay Monahan, helped us sign pitcher Keith Foulke. Keith was a huge hockey fan; Jay was a sports agent working for Bobby Orr, the greatest hockey player of all time. At 11:00 at night, I called Jay; Jay called Bobby, who called Keith. He was blown away. That sealed the deal.

With these players, we were able to pull off the greatest comeback in baseball history and win our first World Series in 86 years. For me, this was personal. My dad, Tom Kennedy, an Episcopal priest, used to take me to Fenway on his standing-room clergy pass and hoist me onto his shoulders to watch the games. After Theo and I received our 2004 World Series rings, we gave them to our dads on Father’s Day. There was no more important relationship to be celebrated.

We won another Championship in 2007, but nothing could prepare our organization for what took place on Patriots’ Day in 2013 when two bombs went off at the finish line of the Boston Marathon. The city was in shock. All of us—especially our players—instinctively knew that we had to play a part in the recovery. Fenway became more than a ballpark. It was the civic gathering place in which David Ortiz grabbed a microphone and defiantly declared this was our city. I’ll bet you remember this—David added an f-bomb that only Big Papi could get away with. Our players knew they were playing for something bigger than themselves. You can draw a direct line from our third World Series title to the bond that formed between our organization and our city that was indeed “Boston Strong.”

He wants to know if we can arrange for a plane to deliver supplies to Puerto Rico, which was battered by Hurricane Maria.” I said, “One hundred percent YES.”

Relationships? Let me tell you one final story. We were wrapping up our contract negotiations in late 2017 with our new manager, Alex Cora, when I got the call from our GM: “Sam, Alex has one more ask.’’ Oh, here we go, I thought. He wants more money, more years, or the biggest hotel suite on the road. “No, no, it’s nothing like that. He wants to know if we can arrange for a plane to deliver supplies to Puerto Rico, which was battered by Hurricane Maria.” I said, “One hundred percent YES.” We arranged a trip to Caguas, Alex’s hometown. Our manager, our front office, and our players brought food and medical supplies there. Alex had taken us home—his home—to offer hope, comfort, and aid.

That trip set a powerful tone of shared purpose, which revealed itself time and again all season. We won 108 games, a franchise record. Our players were never more united in their commitment to each other.

Ironically, it was a loss that defined our winningest season: It happened on the night that refused to end. Game 3 of the World Series against the Dodgers lasted 7 hours and 20 minutes over 18 excruciating innings. On the mound for the last six innings of that game was Nate Eovaldi. Inning after inning, he held the Dodgers at bay, throwing an ungodly 97 pitches before the Dodgers won on a walk-off home run.

If you were still watching at 3:30 that morning, you saw that when Eovaldi came walking off the mound, his teammates were waiting for him on the top step of the dugout. What you didn’t see was a scene back in the clubhouse. Alex Cora told his team, “Years from now, when people talk about this game, they will not talk about who won or lost. They will talk about Nathan Eovaldi and how much he put on the line for all of us.” Our players, some of them in tears, stood and applauded. One by one they embraced Eovaldi with affection, appreciation, and awe. When we left the clubhouse that night, it was not as a defeated team. Alex said later that was the night he knew we were going to win the series.

A week after returning home in triumph from LA, there was one trip left to make. We returned to Caguas to celebrate the end of this magical journey in the place where it began. Relationships? A team from Boston and an island in the Caribbean, forever connected.

For the nonfans in the audience, I am sorry I have burdened you with more baseball in one day than you’ve had to endure in your entire lives. But I hope you understand that you can substitute your own passion for mine, and the message does not change: It’s all in the relationships, Trinity graduates.

For me, Trinity College is family. Recognize, cherish, and nurture the relationships you have forged here, and embrace those that will come your way. Your lives will be so much richer for it. A wise woman named Brené Brown said, “We are hardwired to connect to others, it is what gives purpose and meaning to our lives.” Life is indeed a team sport. I urge you to help each other, look out for each other, care for each other.


Sam Kennedy is President and CEO of the Boston Red Sox. A 1995 graduate of Trinity College in Hartford, he delivered this address to the Class of 2019 at Commencement Ceremonies this month. A copy of the full address can be read here.