From the Field to the Front Office

Harvard alumni executives in sports

The "Fab Five of Harvard Sports" panelists: (left to right) Ben Crockett ’02, Allison Feaster ’98, Don Sweeney ’88, and Jessica Gelman ’97, M.B.A. ’02, alongside Harvard Club president Marcus O.P. DeFlorimonte PMD '95.

The “Fab Five of Harvard Sports” panelists: (left to right) Ben Crockett ’02, Allison Feaster ’98, Don Sweeney ’88, Jessica Gelman ’97, M.B.A. ’02, and Marcus DeFlorimonte, PMD ’95 | PHOTOGRAPH BY MAX KRUPNICK/HARVARD MAGAZINE

A few weeks after her college graduation, Jessica Gelman ’97, M.B.A. ’02, landed in Israel, where she would spend a year playing Euro-League basketball. After her first practice, a reporter asked her “You went to Harvard, what are you doing here?” That question ate at her during her year there—should she try to play internationally and earn a WNBA bench spot, or should she find a new career?

Tuesday evening, Gelman—now CEO of Kraft Analytics Group—joined four other Harvard stars turned sports executives to discuss how the University aided their journeys. Gelman’s path ran through the College, where she studied sports psychology, and the Business School, which she attended a few years after her stint in Israel. At HBS, Patriots owner Robert Kraft watched one of her presentations and hired her. Now, Gelman says she is proud to be “one of few female CEOs in sports, technology, and analytics.”

At times, some of the Harvard Varsity Club panelists struggled with their Crimson ties. While playing minor league baseball, Ben Crockett ’02 tried to distance himself from Harvard. In the Tri-City Dust Devils clubhouse, his teammates lobbed trivia questions at him. Though his alma mater may have induced some teasing, it helped him land a role in the Red Sox’s scouting department following the end of his playing career. Sixteen years and a pair of World Series rings later, Crockett is now the senior vice president of baseball operations for the team.

Like Crockett, the other former collegiate athletes credited their career successes to their time at Harvard, both on and off the field. Allison Feaster ’98, who was featured in the magazine’s November-December 2022 edition, learned to embrace the uncomfortable. Cambridge is a long way from her small South Carolina hometown, and she often felt out of place. But she worked hard: Harvard was “sink or swim,” she said. Grinding her way through college—working two jobs, studying, and setting Harvard’s career women’s basketball scoring record—prepared Feaster for the challenges of the real world. During and after her decade in the WNBA, she played abroad in Europe, often as her team’s only English speaker or person of color. Now, as vice president of player development and operational growth for the Celtics, she is one of few female NBA executives.

Even with storied athletic careers, many panelists still consider graduating from Harvard one of their greatest achievements. Mike Lynch ’77—Harvard football player and 15-time Massachusetts sportscaster of the year—remembers his grandmother weeping at his graduation. She recalled America’s era of anti-Irish discrimination and beamed with pride that Lynch completed college at Harvard. Gelman’s grandmother, on the other hand, was one of NASA’s first employees—but as a woman was confined to secretarial work. “I’ll never forget her looking at me,” Gelman said, “saying, ‘I never thought I would see the day that a woman, let alone my granddaughter, would graduate from Harvard.’”

The panelists understood that their achievements—though lofty—affected the world in a different way than those of their classmates. Helping a team win a championship may not save lives, but it does provide social value. “Sports connect people,” said Don Sweeney ’88, a former Bruins player who is now the team’s general manager. Sports, said Gelman, allow people to watch others “win and lose and fail and succeed”—outcomes that are not so readily apparent in other fields.

At the end of the evening, the panelists offered advice to current Harvard students seeking a career in sports. “There’s no linear path to here,” said Feaster. When her playing career came to a close at age 40, she was anxious about retiring because her classmates were already CEOs and lawyers. “Take your own journey,” she said. “Don’t look left and right.” Crockett suggested that students stay grounded: “Push yourself harder each day. Don’t be stressed that you need to get to a goal….Get small wins each day.”

String together enough wins, and perhaps another Harvard student could wind up with a pair of World Series rings.

Read more articles by: Max J. Krupnick

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