Brian Cashman Agrees to New Contract to Stay Yankees GM

Brian Cashman is staying put. The New York Yankees general manager has agreed to a new contract with the team, he said Wednesday at the club's end-of-season news conference, keeping the longest-serving GM in franchise history in the chair he has held since 1998.

"We've agreed on a new contract," Cashman said, per Yahoo Sports. "We just have to bang out some minor stuff on the backend of it. We're locked and loaded." The length and money have not been released.

Brian Cashman's track record, good and bad

Yankees fans know both halves of this resume by heart. The team has posted a winning record in each of Cashman's 29 seasons as GM, per ESPN, with four World Series titles and 15 American League East titles on his watch. Yahoo Sports counts seven AL pennants in that span, the most recent in 2024.

The other half is the one that fills the call-in shows. The Yankees have not won a World Series since beating the Philadelphia Phillies in 2009. ESPN notes their run of 13 straight playoff appearances without a title is tied for the fourth-longest such streak in MLB postseason history.

This fall stung in a familiar way. New York went 93-68, its third straight 90-win season, then finished second in the AL East behind the Tampa Bay Rays, who swept the Yankees in the ALDS. It was the second straight season the Yankees went out in the Division Series.

Steinbrenner sticks with his leadership group

Owner Hal Steinbrenner made it clear he was not looking for a shake-up. "I know how talented they are and I know how intelligent they are," he said of the front office and coaching staff, per Yahoo Sports. He called Cashman "a good leader, a good listener and very intelligent," and added: "We are ok with this leadership group."

Steinbrenner pointed to injuries and an offense that did not play up to its ability as the reasons the Yankees fell short of the division title.

The Cashman news lands two days after word that manager Aaron Boone is returning for a 10th season, a deal ESPN confirmed through a source. So the same two men who ran the 2026 club will run the 2027 one.

What it means for the winter

Cashman's previous deal, a four-year extension signed in 2022, ran through the end of this season, per ESPN. Now there is no question about who makes the calls when free agency opens, and ESPN's Buster Olney has noted the Yankees have nine free agents to sort through, including David Bednar, Paul Blackburn and Jazz Chisholm.

That is the first test of the new deal. If Chisholm or Bednar walks, Cashman is the one who has to fill it, and Yankees fans will judge this extension by whether the next October finally goes longer than the Division Series.