Fan Forever

In the 15 years since Samantha Barkowski ’09 became a Fenway Ambassador, her responsibilities at Fenway Sports Group have changed dramatically. One thing that hasn’t changed, however, is her focus on the fans.

Story by Sarah Abrams
Photographs by Matt Kalinowski

Samantha Barkowski ’09 grew up a Red Sox fan, but as a child, she visited Fenway Park, baseball’s oldest ballpark and one of Boston’s most beloved landmarks, only three times. The first time was in elementary school, when she won a ticket through the Red Sox Foundation’s Read Your Way to Fenway program. Later, in high school, she attended two games with Milton friends.

That all changed 15 years ago when, in college, Barkowski became a Fenway ambassador, working wherever the team needed her. In the intervening years, her role in the organization has grown dramatically, from ambassador to full-time employee. She rose from executive assistant in the legal department to senior vice president for strategy and growth with Fenway Sports Group (FSG), the Red Sox’s parent company, where she was recently charged with managing FSG’s golf holdings.

From her office located just half a block from the iconic park, Barkowski exuded enthusiasm about the recent investment of FSG and its subsidiary, Strategic Sports Group (SSG), in men’s professional golf and her present full-time focus on seeing that investment succeed. SSG acquired 11 percent of the PGA Tour, which comes with four board seats and some minority rights. “We’re fired up,” said Barkowski, who had just returned from Orlando for the PGA Tour’s annual tournament business meetings.

Barkowski believes that the PGA Tour currently has a lot to offer in the way of entertainment value, but there are ways in which SSG can help improve the tour’s profile. “We’re in just the right spot to make it happen,” she said. “Not only are we positioned to invest in the tour, but we’re also true investor operators. We’re from pure operator backgrounds. I’ve worked customer service at the Red Sox. I’ve worn every hat on the day-to-day of a team operation.”

That operational perspective Barkowski offers began as a Fenway ambassador, where she took on a variety of tasks, from working in the front office fielding phone calls and answering fan mail to acting on game day as chaperone for the national anthem singer to overseeing “meet and greets” with players for their charitable initiatives.

“Catering to the fan was something that was ingrained in me from day one at Fenway,” she said. “They have a policy that we respond to every fan phone call, every fan letter. It’s why I loved being an ambassador. It was really fun.”

After graduating from Harvard College in 2014, and thinking she might eventually pursue a law degree, Barkowski transitioned to full-time work in the general counsel’s office as an executive assistant.

She was concerned that, as a woman, she might get pigeonholed into a string of support jobs, but Ed Weiss, FSG’s general counsel and executive vice president of corporate strategy, made her a promise. “He told me, ‘If you do it and kick ass, give us a year to 18 months and then we can have a conversation about what else there might be,’” she recalled. “I took a little bit of a risk, but I said to myself, ‘Okay, I’m going to trust that won’t happen,’ and, fortunately, I work with incredible people, and he was true to his word.”

And true to her word, Barkowski worked hard, doing what was needed as she gained exposure across the organization’s divisions. Within two years, she was doing hands-on legal work, which helped expose her to the business side of the organization.

In 2018, Barkowski went to work for David Beeston, the team’s chief strategy officer, as a research and intelligence manager. The focus at that time was on FSG Boston (the Red Sox, Fenway Sports Management, and FSG Real Estate).

Barkowski was still thinking about law school, but her new boss offered some advice. “When I went to work for Dave, he said, ‘Give it a year,’” she said. “‘Law school will always be there. Try it out, and if you still want to go to law school, we’ll write you a recommendation.’ So I went to work for Dave, and law school never came up again. I said to myself, ‘I love what I’m doing. Do I really want to go back to school?’”

Several promotions followed and Barkowski advanced in 2020 to director of strategy and growth. In 2021, FSG launched its first strategy and growth team, and a year later, Barkowski was named vice president for strategy and growth. The following year, in 2023, she became senior vice president for strategy and growth. Along the way, she worked on deals such as the purchase of the ice hockey team the Pittsburgh Penguins and the TGL team Boston Common Golf partnership with Rory McIlroy. In March, Barkowski was entrusted to manage FSG’s golf holdings, which include SSG’s investment in PGA Tour Enterprises and the TGL team, Boston Common Golf.

“I often get asked how I ended up where I am, and the answer is not always the answer people want. But there’s no secret or shortcut. I’ve always been available and worn many hats. There are people who say they’re willing to do anything, but when they realize it’s administrative work and filing, they’re like, ‘Maybe not.’”

Barkowski credits her parents with modeling a strong work ethic and Milton for helping her hone it.

Growing up in Dorchester the oldest of five children, she attended Boston public schools before entering Milton in the seventh grade, a transition that wasn’t entirely smooth.

She didn’t realize how much help she needed until high school, when she started receiving grades. “I knew I wasn’t performing to where I had been at my prior school, but I chalked it up to adjusting,” she said. “When I started to get grades, I thought, ‘Oh, this isn’t great.’”

The summer after eighth grade, English teacher Richard Hardy—former chair of Milton’s English Department, Upper School principal, and interim head of school, who later became Concord Academy’s head of school—tutored Barkowski in writing, grammar, and English.

“He helped me learn how to take notes,” she recalled. “There were some basic skills that I hadn’t developed, partly because I just wasn’t as challenged at my other school. I built a great relationship with Mr. Hardy. I often think back on that. I’m not even sure if he remembers me, but he did a lot for me, because by the time I got to high school, I was in better shape. I still struggled, but it got better and better over time. Eventually it clicked.”

But hard work, according to Barkowski, doesn’t tell the whole story of how she got to where she is today. Timing, too, played a critical role.

“Not to undercut myself, because I think I’ve worked really hard to get where I am,” she said, “but at the same time, I’ve been so fortunate that my time in sports coincided with greater and greater institutional investment in the industry and sector.”

In 2010, when Barkowski joined the Red Sox as an ambassador, the organization had 500 employees, all part of the Boston Red Sox and the New England Sports Network (NESN). It had recently bought 50 percent of the NASCAR team Roush Fenway Racing. In 2010, FSG acquired the Liverpool Football Club in the English Premier League (EPL), now one of the most valuable sports properties in the world.

“That’s a testament to FSG’s leadership and ownership,” Barkowski said. “I believe we were the second American ownership group in the EPL, which today is such a giant. It’s become so popular in the United States over the past decade. It’s easy to look back and think, ‘Oh, yeah, that’s obvious,’ but at the time, Liverpool was on the brink of bankruptcy. FSG went over and acquired it for almost pennies on the dollar because it had been run so poorly. Over the past decade plus, we’ve built this incredible juggernaut on both the competition and commercial sides.”

Barkowski describes today’s organization, with close to 2,000 employees, as “opportunistically built.”

She said, “FSG’s investors just saw opportunities like Liverpool Football Club and jumped. It’s really pushed a lot of conglomerates like us to professionalize in a way that sports teams previously have never really been run. They’ve often been family-owned trophy assets where the owners show up to the game and that’s it. Teams have been handed down generation after generation, but over the past 10 to 15 years, that has changed.”

Barkowski is confident that FSG will now apply that same energy and know-how to expanding the PGA Tour. “At the end of the day, we want to create a compelling competition that people feel that they have to tune in for every week,” she said.

“Today the PGA Tour generates about $2.2 billion in revenue. The National Hockey League brings in about $6 billion, Major League Baseball $9 billion to $10 billion, the National Basketball Association $10 billion to $12 billion, and the National Football League about $20 billion. There’s a lot of opportunity there. We think that this business could be three times the size.”

Barkowski is pleased by the progress that has already been made since SSG’s investment in the PGA Tour. The organization is exploring ways to improve the quality of the events, considering how golf might be made more exciting to fans.

Working with former Red Sox general manager and FSG partner and advisor Theo Epstein and members of a working group of PGA Tour employees, Barkowski is looking at possible changes to the game’s rules.

Epstein, who recently worked with Major League Baseball to oversee its new rule changes, “has the expertise and experience to look at a product and help make it more exciting, to create drama and rivalry and really engage the fan and the viewer,” Barkowski said.

She is also working with FSG’s real estate team and the PGA Tour to review its real estate portfolio and options. “I see my role as one of facilitating progress,” she said. “It’s a little similar to maybe an operating partner at a private equity firm. You bring operating expertise and an understanding of what the investors expect to see and the progress they expect to make. You support that effort.”

And she has no regrets about her decision after college to stick with the Red Sox. “The cool thing about working at FSG,” she said, “and we talk about it in our growth and strategy team all the time, is you never know what opportunity is going to present itself and where we’re going to be. If you had asked us 18 months ago about the PGA Tour, we’d be like, ‘What?’ And now, a year later, I’m all golf.”

And how is her golf game, now that she is working full-time promoting men’s professional golf? “I used to play around with my siblings at Franklin Park Golf course in Dorchester,” she said. “They have a caddy program during the summer for kids who grow up in Boston, and my brothers actually ran the caddy program one summer in high school. But I’m not really a golfer.

“I can hit the ball,” she said with a smile, “but I’ve got to work on my game a little bit if I’m going to be playing around with professional golfers.”