After reaching the World Series last season, many expected the New York Yankees to do the same in 2025. Despite losing superstar outfielder Juan Soto, GM Brian Cashman quickly pivoted. The longtime Yankee general manager traded for outfielder Cody Bellinger and reliever Devin Williams in addition to signing lefty starter Max Fried in free agency. While these moves in addition to deals at the trade deadline helped New York return to the postseason, their season ended in the AL Division Series (ALDS). Now, Yanks fans are split on whether Cashman and manager Aaron Boone should return, according to the Athletic's Jordy Fee-Platt in a recent article.

“The Athletic’s readers were asked to share their thoughts on the matter with a poll asking fans to select from four options: fire both, keep both, fire Boone and keep Cashman, or fire Cashman and keep Boone,” wrote Fee-Platt. “It turns out that the fans have mixed thoughts. The most popular answer was to fire both, but the second-most popular was to keep both. So, a vast majority of voters prefer to either keep the status quo or clean house, consisting of 67% of those polled.”

Cashman has been the Yankees general manager since 1998. Boone has been the manager since 2018. The Bronx Bombers have not won a World Series since 2009. For a team that prides itself on their historic past, New York hasn't lived up to the legends of Yankee lore. Now, after another postseason ends in disappointment, the question once again needs to be asked: should Yankees owner Hal Steinbrenner finally pull the plug on the Cashman regime?

Yankees need to clean house in order to capture more titles

New York Yankees outfielder Giancarlo Stanton (27) is introduced with general manager Brian Cashman, manager Aaron Boone and owner Hal Steinbrenner at a press conference during the MLB winter meetings at Walt Disney World Swan and Dolphin Resort.
Mandatory Credit: Kim Klement-Imagn Images
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The younger Steinbrenner has been in charge of the Yankees since 2008, succeeding his father, George. The elder Steinbrenner was one of the most recognizable owners in sports, whose passion for winning rivaled another legendary owner, Al Davis of the now-Las Vegas Raiders. There was no limit to the amount of money Steinbrenner would spend on the team, as his goal for the franchise was to win a World Series each year.

However, it feels as if Hal doesn't quite have the same passion as his father. While the current Yankees owner has shown that he loves the team as well, he's not as present as his father was, leaving things mostly to Cashman and New York's front office. Cashman is surrounded by quite a few long-tenured lieutenants, such as assistant GMs Jean Afterman (hired in 2001) and Michael Fishman (brought aboard in 2005). Although having continuity with so much key personnel remaining on staff, it feels as if the Yankees' leadership has gotten stale.

Despite not winning a World Series since being hired in 2018, it looks as if Boone will be back in 2026. The current Yankees manager is under contract through the 2027 season, so could certainly be back next spring. It also looks like Cashman and his team will be back as well. Although it's too early to tell for certain, it feels as if Steinbrenner will stay the course. After all, there are many reasons why he should do so. New York has made the playoffs in seven of the eight years that Boone has been the manager. That's certainly better than almost the rest of the MLB.

Yet, it's clear that the Yankees have lost their way a bit. Under the elder Steinbrenner, New York would have stopped at nothing to improve the team. Yes, things have certainly changed since the Bombers won their last title in 2009. The luxury tax acts like a salary cap of sorts. A new Competitive Balance Agreement (CBA) will need to be ratified in the near future. If the Yanks stay the course, they could certainly be rewarded with their 28th World Series title next fall. But does Cashman deserve another shot? If Steinbrenner truly wants to get his franchise back on track, it's time to part ways with baseball's longest serving general manager. The sooner, the better.