In Peoria, Arizona, Jerry Dipoto reminisced about a pivotal moment in his transition from player to executive. During a visit to Wrigley Field with former manager Jim Fregosi, an incident involving pitcher Eric Gagne left an impression on Dipoto. After laughing at the strikeout, Fregosi sharply reminded Dipoto of the challenges players face, an insight that steadfastly guides him in his role with the Seattle Mariners. Dipoto is among a select group of former players now leading major league teams’ baseball operations.
Dipoto, who has held the position of president of baseball operations for the Mariners since September 2021, is joined by former players like Chris Young of the Texas Rangers and Craig Breslow of the Boston Red Sox in similar leadership roles. Chris Getz recently took up the position of general manager for the Chicago White Sox, and Buster Posey has become the president of baseball operations for the San Francisco Giants. These transitions underscore the unique perspective former players bring to these roles, blending empathy and credibility in handling team dynamics.
Breslow, who guided Boston to sign Alex Bregman with a strategic contract, brings this balance of experience and knowledge to the Red Sox. The San Francisco Giants, similarly, benefited from Posey’s involvement in convincing Willy Adames to sign a significant deal. Adames highlighted a direct and personal conversation with Posey as influential in his decision to join the Giants.
Both Breslow and Young, who have Ivy League backgrounds from Yale and Princeton respectively, illustrate that traditional academic pathways still hold significant influence in MLB executive leadership. However, the modern player’s awareness of the business and analytical sides of the sport marks a distinct shift in how teams are managed. Chris Getz emphasized the advantage of mixing playing experience with data-driven decision-making, acknowledging that a diverse skill set strengthens an executive’s impact.
Those who have played professionally might face specific biases in executive roles, but Dipoto stresses the importance of building a complementary team that bridges gaps in knowledge. Trusting colleagues with expertise in areas they may not fully understand is crucial to assembling a successful front office. Future leaders from playing backgrounds are emerging, such as Brandon Gomes, who contributed to the Dodgers’ recent World Series success, and Ryan Garko of the Detroit Tigers.
The transition from playing to management isn’t solely about understanding the game but also about curiosity and an eagerness to comprehend the reasoning behind crucial decisions. Breslow noted that those inquisitive about operational strategies tend to succeed in executive positions, revealing the qualities they seek in future leaders within the sport.
