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Q&A: Sam Kennedy on his Brookline roots and the state of the Red Sox

Red Sox team president Sam Kennedy (left) takes in a game at Fenway in 2016 with his father, Rev. Thomas Kennedy. Photo by Stan Grossfeld, Globe Staff, courtesy of The Boston Globe
July 24, 2023

Jonathan Traub, a rising ninth grader at Brookline High School and the author of a Red Sox blog called Sox Watch, interviewed Red Sox CEO and president Sam Kennedy about his Brookline roots and his own sports memories. This transcript has been edited lightly for clarity.

Jonathan Traub: You grew up within walking distance of Fenway Park. You also had access to your dad’s clergy pass. How often were you able to make it to games? What are some of your fondest memories?

Sam Kennedy: I was very, very lucky. My dad was an Episcopal clergyman and he was at Trinity Church in Boston and then St. Paul’s Cathedral on Tremont Street in Boston. He was made aware of this clergy pass program in the 1970s. He wrote letters to the Red Sox and the team was kind enough to respond. Each year he got a clergy pass. When I was 13 or 14, I was bold enough to take it out of his wallet and walk down the street and go to games by myself. Security at the gate recognized me. They said, “That’s fine, go ahead.” It started off as $1 and then it was $2. You didn’t get a seat, but you got access. I would come down with my dad, or sometimes I would come on my own or bring my brother or sister or friends because the pass actually said the Reverend Thomas B. Kennedy and guest. I would go to at least 20 or 30 games a year, at least. Fenway was my favorite place in the world. I was lucky to grow up in the Brookline Village area, just a couple of T stops away.

My favorite memory was definitely the 1986 season. I was 13 and of course, the Red Sox made it all the way to the World Series that year. It was heartbreaking in the end, but that’s when I fell in love with the team. My favorite thing was coming early and going to batting practice and running around trying to catch foul balls. Sometimes I’d get three or four balls and bring them home, then try to get them autographed the next day.

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Traub: Did you play sports growing up in Brookline? Did you play at Brookline High School or in any recreational leagues?

Kennedy: I was very lucky to play Brookline youth baseball when I was at Brookline High, and I played ice hockey. Our hockey team played at Larz Anderson Park, so we would sometimes have practices get rained out or snowed out. Baseball was at Eliot Playground/Warren Field off of Chestnut Hill Avenue when I was on the varsity team, and junior varsity was at Amory Playground. I played probably on every baseball diamond in the town of Brookline. I played for Lincoln School. We had a Lincoln School team, and I actually played basketball there. Sports was incredibly important. I just loved being part of a team. I wasn’t a particularly good player, but I just loved the atmosphere. Being around other kids who had common interests in sports, and specifically in my case, in baseball.

Traub: What other memories do you have of Lincoln School?

Kennedy: Lincoln Lions! Back when I was at Lincoln, there was little Lincoln on Walnut Street. And then big Lincoln was further down, closer to Brookline Village on Route 9. I lived much closer to Big Lincoln. My fondest memories from Lincoln sports were when we played kickball before classes started in the morning. When you kicked the ball over the fence, instead of being a home run, it was automatic three outs because the ball would go onto Route 9 and you’d go collect the ball in traffic from the morning commute. So it was a big penalty to kick the ball over the fence and have it go into Route 9.

Traub: What do you remember most about professional sports in Boston during that time?

Kennedy: Definitely the Boston Celtics. It was the days of Larry Bird, Dennis Johnson, Kevin McHale, Robert Parish, and Danny Ainge and, you know, winning championships and always being competitive was really exciting. I was a diehard Boston sports fan. The New England Patriots were not even on the radar, as they are now as an uber-competitive team. Once the pride of Brookline High, Robert Kraft, took over, they had two decades of dynasty-like performance. What I remember the most was wanting to go to a Celtics game or a Boston Bruins game. I certainly didn’t think about going to a Patriots game. You know, the idea of going to Foxborough was like, “Oh, it’s too far away.” That’s sort of laughable now the way people commute and travel around with ride shares or on public transportation. The Boston Garden was sold out for every single game for the Bruins and the Celtics and you couldn’t get tickets unless you were a season ticket holder or you knew somebody and so Fenway was the most accessible in those days. I was spoiled to have the clergy pass but you could also come down to buy a ticket on the day of a game. That sort of mindset and mentality was important for us to bring back to the Red Sox when we got here 20 years ago.

Traub: We’re in the first season of the rules changes in Major League Baseball that are designed to speed up the game. What’s your assessment of how the rules have played out so far? Do you think any modifications are necessary?

Kennedy: I would tell you if I thought otherwise but I think they have been absolutely perfect. You know, it’s great to talk to younger fans. The game that we see now on the field is very similar to the game that I saw when I was your age and when I fell in love with baseball. What do I mean by that? There’s more action. There’s less dead time. The game moves along. There are more balls in play. There’s more athleticism. There’s a premium put on speed with the bigger bases. Balls that used to be hit into the shift are now finding their way to the outfield. There’s more offense. It’s really exciting to see what the commissioner’s office has created. And of course, Theo Epstein, who also went to Brookline High, had a hand in creating these rule changes. And so Brookline should be very, very proud of that as well.

Traub: During the off-season, the Red Sox brought in some important guys to the current team, assistant athletic trainer Masai Takahashi, and players Justin Turner, Adam Duvall, and Kenley Jansen. But you also failed to sign Xander Bogaerts and Nathan Eovaldi. If you had to give chief baseball officer Chaim Bloom and everyone involved in player acquisition an overall grade for this past offseason, what would you say?

Kennedy: Our baseball operations department has a very difficult job because we have to do something that’s really difficult, and that is balance the near term with the long term. And so I think when you’re grading them out, you have to think about the goal, which is sustainable winning and being able to have a team that gives you a chance to compete each and every year. Obviously, in 2021, we had a magical season, two games from going to the World Series. We had a bunch of injuries and had a disappointing ’22. Frankly, we’re not performing to the level that we had anticipated or where we’d like to be here in 2023. We’ve got to get back on a streak and get back into the postseason. But in terms of balancing the near term and the long term, Chaim Bloom and the baseball operations department get an A. If they were at Lincoln School or Brookline High, that’s the grade I would give them in terms of where we are as an organization. That’s on all of us that we’re not where we want to be in terms of the 2023 season. We’re probably in the B or B minus range, but I’d say we have a chance to earn an A if we do well in the third marking period and fourth marking period for our report card. But fingers crossed we’ll start to perform better.

Traub: Since you joined the Red Sox in 2002, the team has won four world championships, which is the most by any Major League Baseball team during that stretch. Probably the most memorable was in 2004 when the team broke the 86-year curse by beating the St. Louis Cardinals. What do you remember most from that night in St Louis?

Kennedy: I remember being completely and totally sleep-deprived all of October of 2004. What I remember the most was that I was very lucky to be surrounded by some very close family friends who I grew up with in the Boston area who had tickets right near us. We were celebrating on the field. But I remember calling back home to my wife. My mom and dad were there with some of their friends. All Brookline natives, they were out at our house. And I just remember talking to them and just sort of echoing Joe Castiglione. Everyone has just kept saying, “Can you believe it? Can you believe it? Can you believe it?” And then I think I lost the cell service because everyone from Busch Stadium in Saint Louis was trying to call home.

We then had a celebration at the hotel afterwards and stayed up until, you know, four or five in the morning. And then we flew home. And so we pulled back into Fenway Park as the sun was coming up. That was just sort of a spiritual moment. It just didn’t seem real that we had actually won. And you’re so tired and sleep-deprived from travel and logistics and all the work that goes into a postseason. I remember all of it not seeming real at the time.You felt like you were living in a dream. And as I look back at lots of the tapes and interviews and pictures, first of all, you’re like, “Wow, we all looked young!” And the second thing is, I don’t think even we realized the magnitude of what was happening as we were living through it. It was so, so historic.

Traub: What accomplishment would you say you are most proud of with in your time with the Red Sox? And what is something that you wish you could have a do-over on?

Kennedy: Wow, there’s probably so many do-overs! I’ll think about that while I answer the first part. Obviously, personally, I’ve been very blessed with family and things like that, but professionally, in June 2005, on Father’s Day, Theo Epstein and I gave our dads our World Series rings for a Father’s Day gift. And it was super emotional. I’ve got a picture of that moment in my office, and it reminds me of how lucky we are to be in baseball, how special it was to be a part of that season.

And thanks to John Henry and Tom Werner and Larry Lucchino, our bosses, because they allowed us to share in this moment with our families. It’s really important because, you know, if you’re in sports, it’s quite a commitment of time. So being able to involve my family in the professional accomplishment was really special. I’m very proud of that.

In terms of the do-overs, I try not to spend a lot of time regretting things that haven’t gone well. But I’ll say the years where we’ve been right there, 2021, 2017, 2016, 2008 … 2017. You know, when you’re knocking on the door of a World Series championship, you think to yourself, what could we have done differently to put us over the edge — just because we know how hard it is. In the years where we had success, but we didn’t get to the ultimate finish line, those are the ones that eat at you the most. That that would be one. And then one other thing that I think is probably the hardest in baseball — I don’t think there’s necessarily a do-over — but when you have to part ways with star players, when you’re unable to sign long-term extensions with guys.

Going all the way back to Pedro Martinez, in the early days of being here or a Mookie Betts or a Xander Bogaerts, players who meant so much. We were able to sign guys like David Ortiz and Dustin Pedroia and Rafael Devers. But the players who meant so much to so many fans, when we weren’t able to line up on deals for either economic reasons or other reasons … those are the ones that you say, “What could we have done differently to ensure that they stayed a part of the Red Sox forever?” Knowing that there’s reality, you can’t sign everybody, but those are the ones that stay with you and that you think back and say, “Was there something I could have done differently to have avoided that player leaving the organization?” Those are the ones that are difficult.

Traub: In 2014, the Red Sox started the Student9s program to try to get more kids to Fenway Park. Would you say it has been successful?

Kennedy: Yes, we’re very proud to report that on any given game at Fenway, we may have up to 3,000 to 4,000 students. We welcome middle school students, high school students, and college students. You just show an ID. We have tickets available for $9 for all games. It’s really a throwback to the years gone by when you could just walk up to Fenway and come in on the day of game. You don’t have to make an advance purchase decision. We found that students really liked that. It has been a very popular program.