Major League Baseball is undergoing a seismic shift as former players like Jerry Dipoto and Buster Posey ascend to leadership roles in baseball operations. With five ex-players currently steering front offices, teams are leveraging their on-field expertise to reshape roster strategies, free agency negotiations, and organizational culture.
Dipoto, Seattle Mariners’ president of baseball operations, credits his playing career for instilling empathy.
Recognizing how hard this game is shapes every decision,he said. Similarly, Boston Red Sox executive Craig Breslow—a Yale graduate and World Series champion—emphasizes credibility:
Understanding both sides of a transaction builds trust with players.
This trend isn’t limited to veterans. At 37, Posey convinced star shortstop Willy Adames to sign a $182 million deal with the Giants through candid, agent-free talks. I bought into his vision completely, Adames revealed.
Key factors driving this shift:
- Player familiarity with advanced analytics used in modern front offices
- Demand for leaders who balance data with human-centric decision-making
- Growing emphasis on recruiting former players into executive pipelines
While Ivy League graduates still dominate front offices, teams like the Rangers (Chris Young) and White Sox (Chris Getz) prove playing experience strengthens résumés. You need people who’ve lived the grind, said Getz.
With rising stars like Dodgers GM Brandon Gomes and Tigers assistant Ryan Garko gaining influence, this trend shows no signs of slowing. As Breslow notes,
Curiosity about the ‘why’ behind decisions separates future leaders.For MLB, blending diamond-tested instincts with front-office analytics might just be the next competitive edge.
