More ex-MLB players may enter baseball operations

Former MLB Players Making Their Mark in Baseball Operations

Shortly after hanging up his cleats, Jerry Dipoto attended a game at Wrigley Field alongside former big-league manager Jim Fregosi. During the game, after watching Eric Gagne strike out a batter with a devastating pitch, Dipoto chuckled—only to be met with a firm slap on the back of his head.

“He told me, ‘I’m just going to remind you today … Don’t ever forget how hard this game is to play,’” Dipoto recalled. That lesson stuck with him throughout his journey to becoming the president of baseball operations for the Seattle Mariners.

Dipoto is now part of an exclusive group of former players leading major league front offices. At 56, he has held his current role with Seattle since September 2021. Others who have followed a similar path include Chris Young, 45, who was promoted to president of baseball operations for the Texas Rangers, and Craig Breslow, who took on the role of chief baseball officer for the Boston Red Sox in 2023. Chris Getz was named general manager of the Chicago White Sox the same year, while Buster Posey, a three-time World Series champion and former MVP, became president of baseball operations for the San Francisco Giants.

“There are plenty of highly successful executives who didn’t play professional baseball,” Breslow noted. “But having been on the field provides a level of credibility and understanding. I’ve been on every side of a negotiation, and I know firsthand what players go through.”

That firsthand experience has already played a crucial role in major roster moves. Under Breslow’s leadership, the Red Sox signed Alex Bregman, fending off competition from the Cubs and Tigers with a three-year, $120 million contract. Meanwhile, the Giants struggled to attract a marquee free agent until Willy Adames agreed to a seven-year, $182 million deal—largely due to Posey’s influence.

“My meeting with the team was just me and Buster. No agent, no front office—just us,” Adames revealed. “We had a deep conversation, and I bought into his vision for the organization.”

While former players leading front offices is nothing new, today’s athletes are more engaged with the business and analytics side of the game than ever before. Many players now enter management with a strong understanding of data-driven decision-making, making their transition smoother.

Chris Getz, 41, emphasized how much the landscape has evolved. “A decade ago, we weren’t using the same level of data to make decisions. Now, there’s so much information at our disposal, and having a playing background strengthens your résumé.”

However, a playing career doesn’t automatically translate to front-office success. Dipoto acknowledges that while experience on the field is valuable, it also creates potential blind spots.

“I had to learn to trust those who are smarter than me in certain areas,” he admitted. “Sometimes, your desire to be a good teammate clouds your judgment. You have to separate personal loyalty from what’s best for the team.”

Several other former players are on track to join the growing list of player-turned-executives. Brandon Gomes has played a key role in the Los Angeles Dodgers’ front office, helping them win the 2020 World Series. Ryan Garko was promoted to assistant GM for the Detroit Tigers, and Cole Figueroa holds the same role with the Texas Rangers. The Yankees’ Kevin Reese and Tim Naehring, as well as Josh Barfield with the White Sox, are also rising stars in baseball operations.

For Breslow, the key to identifying future executives lies in curiosity. “You can tell who has the potential by the questions they ask. The ones who want to understand not just what decisions are made, but why, are the ones who can successfully transition into this world.”

As more former players embrace leadership roles in front offices, the game continues to evolve, blending traditional baseball instincts with modern analytics. It’s clear that playing experience, combined with business acumen, can be a powerful formula for success in today’s MLB.