Shortly after his playing career ended, Jerry Dipoto took in a game at Wrigley Field with former big league manager Jim Fregosi. After a particularly nasty strikeout by Eric Gagne, Dipoto laughed.

Fregosi promptly slapped Dipoto on the back of his head.

“He said, ‘I’m just going to remind you today. ... Don’t ever forget how hard that it is to play,’” Dipoto recalled. “And that’s what I think is the thing I remember most, and I think the benefit of the guys who have gone through it, is that they recognize that it is a really hard game.”

That lesson stayed with Dipoto as he made his way to his current job with the Seattle Mariners — and membership in an exclusive club. Dipoto is one of five former major leaguers serving as the top baseball executive for a big league franchise at the moment.

Dipoto, 56, has been the president of baseball operations for Seattle since Sept. 1, 2021. Like Dipoto, Chris Young, 45, was promoted from general manager to president of baseball operations for the Texas Rangers on Sept. 13. Craig Breslow was hired as the chief baseball officer for the Boston Red Sox on Oct. 25, 2023, and Chris Getz was promoted to GM of the Chicago White Sox on Aug. 31, 2023.

Buster Posey, 37, joined the list when the former All-Star catcher was hired as president of baseball operations for the San Francisco Giants in September.

“There are a ton of incredibly successful executives who didn’t play baseball,” said Breslow, 44. “I don’t think it’s a prerequisite, but I do think it provides a level of credibility and empathy given I’ve kind of been on every side of a transaction, or every side of a conversation I’ve had to have with a player or coach. And credibility in terms of really being able to understand what players are thinking about, what they’re going through.”

Under Breslow's leadership, Boston used a complicated contract structure to add Alex Bregman in free agency. Bregman also was being pursued by the Cubs and Tigers before he agreed to a $120 million, three-year deal with the Red Sox.

San Francisco had been struggling to land a major free agent before shortstop Willy Adames agreed to a $182 million, seven-year contract with the Giants in December. Adames said Posey played a major role in his decision.

“My meeting with the team, it was me and him, basically. No agent. Nobody,” Adames said. “So we had a really, really good conversation, and I bought into his plan for this organization, for what he wants to build here in the near future.”

Breslow has a degree from Yale and Young graduated from Princeton, so the five players in charge of major league teams doesn't exactly represent some sort of counterrevolution when it comes to Ivy League grads in baseball.

But today's major-leaguers are increasingly savvy when it comes to the business side of the game, and they have firsthand experience with the data used by front offices as part of their decision-making process.

“Where we were a decade ago to where we are now, there's just so much opportunity to make better decisions nowadays based on the information that we have,” said Getz, 41. “But being well-versed in it now, you know having a former playing background is only going to position you, your résumé is just stronger.”

While that big league career is an asset in a variety of ways, it also creates a unique set of blind spots. Building out a front office that complements one another is key, Dipoto said.

“I learned to adapt along the way to things I didn’t know and to trust people who are smarter than I am to fill in those gaps,” he said, “and to recognize when I’m allowing my want to be a good teammate and my want to love the good teammate, sometimes, you have be able to discern when that doesn’t equal best player fit for this situation.”

There are several more people in position to join the club one day. Brandon Gomes helped the Los Angeles Dodgers win the World Series last year, serving as the team's GM under Andrew Friedman. Ryan Garko was promoted to assistant GM with the Detroit Tigers in May. Cole Figueroa is an assistant GM for the Rangers.

Kevin Reese and Tim Naehring work for longtime New York Yankees general manager Brian Cashman, and Josh Barfield is part of Getz's front office with the White Sox.

When it comes to his discussions with players interested in working in baseball operations, Breslow said the conversations provide an indication of the potential for success.

“It becomes pretty clear, generally who has the curiosity, who asks a lot of questions,” he said. "Who wants to learn why we make decisions not just what decisions are being made. Those are the people (that could make the transition).”