In Peoria, Arizona, Jerry Dipoto reflects on a pivotal moment in his career transition from player to executive in Major League Baseball. During a visit to Wrigley Field with former manager Jim Fregosi, Dipoto showed amusement at a strikeout handled by Eric Gagne. In response, Fregosi reminded him with a friendly smack on the head of the difficulties of playing in the big leagues. This lesson of appreciating the challenges faced by players sticks with Dipoto as he climbs the ranks to his current role with the Seattle Mariners.
Dipoto is now one of a select group of former MLB players who have ascended to leadership roles in baseball organizations. Serving as president of baseball operations for the Seattle Mariners since September 2021, Dipoto stands among peers including Chris Young of the Texas Rangers, Craig Breslow at the Boston Red Sox, Chris Getz of the Chicago White Sox, and newly appointed Buster Posey with the San Francisco Giants.
Breslow emphasizes that while playing experience isn’t essential for success in executive roles, it does provide a unique perspective and level of credibility. This insider knowledge can enhance empathy and understanding during interactions with current players and coaches, given their shared playing experiences. With Breslow at the helm, the Red Sox secured Alex Bregman on a significant contract, demonstrating his ability to capitalize on his player insights.
Similarly, the Giants successfully negotiated a substantial deal with Willy Adames, due in part to Posey’s influence as a former player and now executive. Adames credited his positive conversations with Posey as a significant influence on his decision to join the team.
Despite the influx of former players in executive positions, this does not detract from the continued influence of Ivy League-educated leaders like Breslow and Young. The evolving landscape of baseball emphasizes data and strategic decision-making, offering former players like Getz an advantageous position due to their comprehensive understanding of the game from both a performance and business perspective.
Dipoto acknowledges that while a playing background is beneficial, it is essential to build a multifaceted team capable of complementing each other’s skills, thereby addressing any potential blind spots he might have. This mix of expertise ensures sound decision-making within the organization.
The presence of former players in front offices is expanding, with promising individuals like Brandon Gomes, Ryan Garko, Cole Figueroa, Kevin Reese, Tim Naehring, and Josh Barfield poised for future leadership roles. When evaluating potential candidates for baseball operations roles, Breslow looks for a natural curiosity about the mechanics of decision-making, an indication of who might successfully transition into these pivotal roles.
