For an organization once known for its brutal hiring and rehiring practices, Brian Cashman has lasted over two decades with the New York Yankees. Having seen its rise and fall from the era of Derek Jeter to the age of Aaron Judge, the general manager remains secure in his position. But is it all about to come down?

Cashman was originally employed by George Steinbrenner III, and his son Hal Steinbrenner remains equally enamored of him. However, looking at the fans’ perspective, Bronx baseball lovers think it’s time for a change. The Yankees are experiencing one of their worst years in franchise history and fans want ‘out with the old, in with the new.’ But will the GM’s contract allow it?

Brian Cashman’s Recent Contract With the New York Yankees

On Dec. 5th, 2022, the Pinstripes sealed their fate with another four years of Brian Cashman in the front office. A four-year extension means the GM will stay with the team throughout the 2026 season. Maintaining the position since 1998, Cashman is one of the longest-tenured general managers the league has seen. And fans wish his achievements in the almost three decades would speak for it.

Cashman’s Achievements in the Bronx

The year a young Cashman took over the role from Bob Watson, the Bronx Bombers won a World Series. Then the year after that, and another year after that. The next Fall Classic pennant came nine years later in 2009, and the Yankees haven’t won since.

To his credit, in addition to four World Series, the Yankees GM also boasts six American League Pennants. The early era of his reign was an unbeaten Yankees dynasty. But the last decade has not been kind to the Bronx and Cashman seems disinterested in changing their fortunes.

What Does Yankees Owner Hal Steinbrenner Think of Cashman?

Blind faith! Or at least that’s what it seems like whenever Hal Steinbrenner talks about his front office. Despite the Yankees’ continued woes, Steinbrenner seems bent on giving his trust to Cashman no matter what. Contrastingly, his father’s time was a drastically different era. George Steinbrenner III was famous for his firing and hiring practices, always taking a day-to-day interest in his team, despite being the owner.

Hal, on the other hand, is rarely even seen at games and never wants to disturb the status quo. What is, will be. To his credit, when the Bronx team started falling apart at the seams early on in 2023, the son did try to give an ultimatum. If the Yankees failed to make playoffs again this season, he would be asking some tough questions of the management.

But will it be Aaron Boone or Brian Cashman thrown under the bus? In early August, it seemed like the answer was Boone. Bob Klapisch of NJ Advanced Media reported, “The idea (of firing Cashman) isn’t even on the table. It’s not up for discussion.” So fans should expect to say goodbye to Boone but not Cashman?

How Is Cashman’s Relationship With Yankees Manager Aaron Boone and Captain Aaron Judge?

It’s a harsh reminder each time that while baseball may be a sport that the players and fans enjoy, it’s also a business. At the end of the day, team management must do what is best for the club; something that will not always be liked by the players, be their decisions to handle things right or wrong. The same goes for Aaron Judge, who was upset with Cashman when details of his offered contract were made public last year before he signed to be with the Pinstripes for life.

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While things may be better for Boone and Cashman on another level, their respective jobs and job security may not allow for a good relationship. It’s Aaron Boone who faces heat from fans and media at every game because he has to work with a roster constructed by Cashman. One has been here longer than the other and, from the looks of it, may outlast him in New York.

What Do the Legends of New York Yankees Think About Cashman?

Unfortunately, the Aaron Judge contract leak was not the first of its instances. When Derek Jeter famously hit free agency in 2011, he was in talks with the Yankees for an extension. In an effort to put media and fan pressure on the captain, Brian Cashman leaked the numbers offered by the Yankees. This was after Jeter had specifically asked to keep it under wraps.

Needless to say, he wasn’t happy, and their relationship wasn’t the same ever again. In 2010, the general manager had even once told the then Yankees captain that he would rather have Troy Tulowitzki playing shortstop for the Yankees. If that’s not a way to sour a relationship, what is?

A boss and his employees will, of course, clash from time to time, but Alex Rodriguez once angered the GM beyond belief in 2013. The former slugger had been in rehab for hip surgery when he announced on Twitter that doctors had cleared him to play. No such announcement came from the Yankees, who had apparently been planning to not let Rodriguez play for a bit longer.

So Cashman, in a fit of anger, told ESPN’s Andrew Marchand, “You know what, when the Yankees want to announce something, [we will]. Alex should just shut the f— up. That’s it. I’m going to call Alex now.”

Is Cashman Going to Stay With the Yankees Forever?

To Bronx fans, it seems like a very real possibility right now. His contract may only last until 2026 for now, but given Hal Steinbrenner’s disinclination to shake things up, he will willingly grant another extension. What New York needs is a revolution, not stagnant waters, and they’re shouting it at whoever will listen.

But only time will tell who gets to stay, who gets to go, and whether the New York Yankees will ever return to their former glory.

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