Kevin Reese is the 'hot name' to succeed Brian Cashman as Yankees GM

Over the past few years, as I reported a book about the history and inner workings of the Yankees’ front office, team employees often asked their own question during interviews: was general manager Brian Cashman planning to step aside after completing his current contract in 2026?

Speculation about this was, and is, widespread in the organization.

One day last summer during an interview in Cashman’s office, I asked him directly. He shrugged and declined to respond.

A few weeks after that, standing in the dugout during batting practice, I tried again.

Cashman, the longest-tenured GM in the franchise’s storied history, said, "The way I have always looked at it, I don’t know what is going to happen a few years from now or 10 years from now. I could get let go during the deal."

That is highly unlikely to happen, but Cashman didn’t want to take the conversation any further.

And to be clear, there is no indication that the GM has decided either way if he wants to continue in the role beyond his current four-year contract, which he signed in late 2022.

But if he were to step away after the ’26 season, or begin a transition process sooner, there is a widespread belief throughout the organization that vice president of player development Kevin Reese is the current frontrunner to succeed Cashman. I heard this from no fewer than five well-placed sources.

If a time comes when Cashman decides to retire or kick himself upstairs to an advisory role, he would be comfortable recommending Reese as a logical heir, say people who work closely with the GM.

"He is the hot name," one of the sources said.

Cashman declined comment for this article.

Several sources also pointed to VP and assistant general manager Michael Fishman, long respected by Cashman for his pioneering work in quantitative analysis, as a potential candidate.

Pro scouting director Matt Daley has earned a reputation in the industry as a potential future GM for someone.

Reese, 46, has the type of varied resume that the Yankees have long valued in baseball operations. A former outfielder, he played 12 games for the Yanks between 2005 and 2006. After retiring, he worked in former assistant GM Billy Eppler’s pro scouting department.

Eppler and Cashman’s idea in designing that department was to seek out evaluators who blended playing or field experience with an openness to analytics.

In 2007, Eppler hired former MLB infielder Tim Naehring as a scout, and Naehring became the Platonic ideal of what the team sought.

He is now VP of baseball operations, and has long been Cashman’s most trusted evaluator  — "my Gene Michael," as Cashman often calls him, referring to the former GM and legendary scout. Naehring thrives in his current role and has passed on multiple opportunities to interview for GM openings across the game.

The Yankees hierarchy views Reese as a hybrid in that Michael/Naehring tradition – vitally important to a team that strives for a balance of what is often reductively called old and new school.

In addition to his experience in pro scouting, where he eventually ascended to director of the department, Reese has been in charge of player development since November 2017.

That scouting/player development mix recalls a vaunted figure in Yankees history, Bill Livesey. At various points in the 1970s, ‘80s, and ’90s, Livesey moved between both of those spaces. Cashman considers him a key and highly underappreciated figure in creating the ’90s dynasty.

Between Michael, Livesey, Cashman and a few others, the Yankees front office features continuity in both personnel and philosophy that no other baseball organization can match. The elevation of Reese (or of Fishman, who is coming up on 20 years with the team) would continue that tradition.

In his player development role, Reese is based in Tampa, as are many members of the Steinbrenner family. He is highly respected by that family, sources say.

And he is close with a younger group of team officials poised to have influence on the team for years to come, from Hal Steinbrenner’s nephew and potential successor, Stephen Swindal Jr., to director of baseball operations Matt Ferry. Swindal is the grandson of George Steinbrenner and the son of Yankees general partner Jennifer Steinbrenner Swindal.

Cashman has been with the Yankees since arriving as an intern in 1986 and has been GM since 1998. Many rivals speak in awe of the fact that the Yanks have never endured a losing season on his watch.

In an interview for my book, The Yankee Way, which Doubleday will release on May 21, longtime Oakland Athletics GM Billy Beane expresses that perspective in strong terms.

"Based on Brian’s accomplishments, I would make the argument that he is the greatest executive in the history of the sport," Beane, of Moneyball fame, told me. "He has four championships and the longest tenure. It’s not unlike Tom Brady’s career, from an executive standpoint. He is the Tom Brady of GMs."

Brady eventually retired, though he stretched his career out for as long as possible. Perhaps Cashman will do that, too – after all, the Yankees are the only life he has ever known as an adult, and he has declined opportunities to leave before. Maybe he’ll stay long enough to lose Reese to another organization.

But all things must pass eventually. And the current belief inside the Yankees is that Reese is well-positioned for whenever that time comes.