
New York Yankees general manager Brian Cashman’s contract expires at the end of the 2026 season. However, that doesn’t mean he won’t be back in 2027. Jon Heyman of the New York Post reports that the Yankees are planning to ask Cashman to return.
That, of course, means that the Yankees will extend Cashman at some point. The Yankees are on track for a 29th consecutive winning season under their current general manager. Seven more wins this season would guarantee that figure.
Cashman has been the Yankees’ general manager since the 1998 season. Over his tenure, the club has won a total of five World Series championships. However, their latest came in 2009.
Despite putting themselves in a good position to contend year after year, the club hasn’t found a lot of postseason success. Since their last World Series championship in 2009, the club has only one American League pennant.
Yankees Expected to Bring Back Brian Cashman in 2027

Entering play on August 28, the Yankees are 75-58 and four games back of the Tampa Bay Rays for the American League East lead. Even without the division, the club is still in a good spot for hosting postseason games.
Despite injuries to their starting rotation and starting lineup, the Yankees are set to make the postseason for the 24th time under Brian Cashman. The rotation has held up fairly well, but their ability to score runs has been impacted.
Aaron Judge’s injury is the most high-profile of the group. The four-time MVP winner has been sidelined since the start of June due to a fractured right ribcage. Judge is the aircraft carrier of that lineup, so it’s no surprise the team is struggling to score runs without its best hitter.
Without Judge, the Yankees’ offense has imploded. They have scored the third-fewest runs (277) and have the second-lowest wRC+ (88) among the 30 MLB teams. However, they’ve managed a 39-35 record despite their offense struggling for the better part of three months.
Much of that has been how well their rotation has gotten. Cam Schlittler’s breakout, plus Ryan Weathers and Will Warren’s reliability, have enabled the club to weather injuries to Gerrit Cole, Max Fried, and Carlos Rodon. At full strength, the Yankees boast one of the top rotations in MLB.
Considering what’s happened to the club, the Yankees feel that Cashman has done his best to put them in a good position to contend this season.
What This News Means for the Yankees

The Brian Cashman news is a good sign for their front office. The Yankees will likely extend the 59-year-old; the question will be for how long.
However, the same might not be said for manager Aaron Boone. Despite loaded rosters year after year, the Yankees have only one World Series appearance under Boone. He’s under contract for one more season.
Once Cashman gets extended, he’ll become the leading authority deciding Boone’s fate as manager. Presumptively, the Yankees skipper will serve out his contract unless they meet an unexpectedly early postseason exit.
Yankees Get Good Brian Cashman News Ahead of Red Sox Series