It's been 17 years since the New York Yankees won their 27th World Series title. During that timeframe, the Yankees have only returned to the Fall Classic once, falling in five games to the Los Angeles Dodgers two Octobers ago. Yet, despite the lack of championship hardware, New York will likely enter 2027 with the same leadership duo. Per MLB.com's Bryan Hoch, the industry thinks that Bronx Bombers owner Hal Steinbrenner will retain both GM Brian Cashman and manager Aaron Boone ahead of next season.

“Boone is under contract through 2027, which would be his 10th season,” wrote Hoch. “Cashman’s contract expires this winter; he has held the position since 1998. While ownership has not commented on Cashman’s status, industry reports suggest Steinbrenner has no desire for a change.”

If Steinbrenner brings back both Cashman and Boone, then one has to assume their seats will be hotter than ever. Cashman will have to sign a new deal, so he'll likely stay for at least a couple more seasons. It's also safe to assume that Boone will manage 2027 without an extension. That way, if the Yankees fall short once again in 2027, then it will be easier for Cashman and Steinbrenner to potentially bring in a new dugout boss.

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After the Yankees' latest early playoff exit, a host of players, most notably Aaron Judge, spoke to the press. Judge, the Yankees captain, missed a good chunk of the season, plus the entire postseason, due to injuries. At 34 years old, his window to lead a title team is closing. If Cashman and Boone fail once again to win New York's 28th World Series title next fall, Steinbrenner will likely be forced to let go of at least one of them, if not both. Will Boone and Cashman finally bring a title back to the Bronx together next year? If so, then expect to see both men leading the franchise for the foreseeable future.