Should The New York Yankees Fire Brian Cashman?

The longtime Yankee GM has put the team on an uncertain path for the future.

Troy Taormina-USA TODAY Sports

Change is needed in the New York Yankees organization.

The team currently stands at an uninspiring 55-51, in last place in the AL East, and are 3.5 games out of a wild card spot. Notably, they have one of the worst lineups in the league (especially without Aaron Judge) full of aging veterans and fringe players, with only one top prospect (Anthony Volpe) playing at the major league level. The starting rotation and bullpen have both been inconsistent throughout the season, and the outfield defense has taken a step back (largely due to non-natural outfielders like Jake Bauers and Isiah Kiner-Falefa being inserted there).

However, the trade deadline provided some hope to improve the team or sell off assets at the right price. The Yankees had multiple different directions to go in.

One option was to be buyers and trade for team needs. In particular, the team badly needs a true left fielder, something that wasn’t addressed during the offseason, while catcher and third base were also notable needs.

Another option was to sell off impending free agents and possibly get some value for them. Luis Severino, Harrison Bader, Wandy Peralta, and Isiah Kiner-Falefa, among others, are in the final year of their respective contracts, and it would make sense to ship off a player the team doesn’t intend to keep and get either prospects or cash back. The players shipped off could be replaced by highly regarded prospects who are major league ready, such as Oswald Peraza.

Of course, another option is to do both of these things. But general manager Brian Cashman chose a different option; to do neither.

The Yankees did next to nothing before the 6 p.m. (E.T.) deadline on August 1. Their only acquisitions were reliever Keynan Middleton from the Chicago White Sox, and Spencer Howard from the Texas Rangers, neither of which were particularly impactful moves or addressed team needs. New York still has a huge hole in left field and one of the worst lineups in baseball.

This leaves the organization in the worst spot they could be: mediocrity. They aren’t good enough to make a serious run at a World Series (unless underperforming players completely turn their seasons around), but the team has too many talented veterans (mainly Aaron Judge and Gerrit Cole) to initiate a full rebuild. The future is uncertain, and despite the team’s current standings (only 3.5 games out of the last playoff spot), a Yankee season hasn’t looked this hopeless since their most recent last-place finish in 1990, a season that was marked by Bucky Dent being fired at Fenway Park and George Steinbrenner being temporarily banned from baseball.

There needs to be notable change in the organization if the Yankees want to compete for a World Series title, an expectation that the front office has gone as far as to promise the players and fans. This change needs to start at the top, and it would be a very bold decision:

Brian Cashman’s job security should be questioned. Despite being brought back on a four-year deal during the previous offseason, there is a legitimate case to fire him.

Cashman has been the team’s general manager since 1998, and has been involved with the organization since 1986. In 2023, it’s become obvious that the game has passed him by.

The biggest evidence of this is his behavior during this trade deadline; according to a rival executive, the Yankees have been frustrating to negotiate with, and felt that they were in “in-between land waiting to be bowled over for their rentals”.

"Yankees have been frustrating this deadline," a rival executive said, who got the sense that they were in "in-between land waiting to be bowled over for their rentals."

— Marc Carig (@MarcCarig) August 1, 2023

This behavior isn’t new from Cashman, as he has become notoriously stubborn with his handling of the organization, priding himself on under-the-radar moves instead of making clear upgrades, while touting an inherently flawed version of analytics.

The definition of analytics is to use data to operate a team at peak efficiency, discovering things that can’t be seen with the eye test. However, analytics don’t care for the idea of a good player, they just want good players who can perform now.

Many of Cashman’s under-the-radar moves are for the idea of a good player. Some of them have worked out over the years, such as Didi Gregorius, Luke Voit, Matt Carpenter, Gio Urshela, and numerous bullpen arms such as Clay Holmes and Wandy Peralta. However, he’d also give $17 million to J.A. Happ when he could have gotten Bryce Harper or Manny Machado for $25 million and $30 million, respectively, in 2019.

In 2022, he passed on shortstops such as Corey Seager and Carlos Correa but was willing to pay $25 million a year for a declining Josh Donaldson just to use Isiah Kiner-Falefa as a stopgap for Anthony Volpe… by playing him in a position that he wasn’t comfortable playing (fortunately, IKF has found a new role as a utility man). This isn’t analytics, this is stubbornness.

This also explains Cashman’s tendency to acquire injury-prone players. Although the team’s current key contributors include Giancarlo Stanton, Anthony Rizzo, DJ LeMahieu, Luis Severino, and Carlos Rodon, among others, the Yankees rarely had a fully-healthy team playing. This doesn’t even get into the 2022 trade deadline acquisitions (Andrew Benintendi, Frankie Montas, Scott Effross, and Lou Trivino, all of whom got injured during their tenures) or the injury troubles of former contributors Luke Voit and Aaron Hicks. Cashman built the team on the idea of these players staying healthy (including Aaron Judge), and ultimately they wouldn’t.

This flawed approach, however, also gives Cashman and the front office easy excuses when the team fails; more often than not, they blame injuries or ill-timed slumps for their inability to win big games, conveniently ignoring that Cashman is the one who brought in these players in the first place. The lack of accountability has also trickled down into the team itself, even blaming the roof being open at Minute Maid Park for losing Game 2 of the 2022 ALCS.

Cashman even treats players coming back from injuries as “player acquisitions”. He did this in 2019, when the Yankees needed a piece or two to get themselves over the top, and he did it this year, when the team was in desperate need of a re-tool.

Brian Cashman: “We’re in it to win it. We stayed the course because of that.”

He mentioned the returns of Nestor Cortes and Jonathan Loáisiga as boosts the rest of the way.

“This was the best play for us with the team we have, still within striking distance.”

— Max Goodman (@MaxTGoodman) August 1, 2023

In 2023, all of the issues the team had would come to light, and they’ve dealt with them all season long. Veterans like Stanton, LeMahieu, Rizzo, Severino, Rodon, and Nestor Cortes Jr. have dealt with both injuries and ineffectiveness, Volpe is dealing with MLB growing pains (barely playing in Triple-A could have hurt his development), and while Jake Bauers and Willie Calhoun provided flashes of upside, it makes no sense to play them and Franchy Cordero over MLB ready prospects such as Oswald Peraza, Andres Chaparro, Everson Pereira, and Estevan Florial. This stubbornness has also affected Austin Wells’ path to the majors, as he was only recently moved up to Triple-A despite offering better hitting advice to Volpe than the team’s hitting coach.

Despite all these issues, Cashman stayed pat at the deadline and will continue to operate the team the same way. He wants to win a World Series, but he wants to do it his way. Maybe this is because he realizes that out of his four World Series rings as GM, he only built the 2009 team; the 1998-2000 dynasty was built by Gene Michael.

These criticisms merely scratch the surface of Cashman’s mistakes during his GM tenure; this doesn’t even get into his tendencies to anger his star players (Aaron Judge is a recent example, but remember he did the same thing to Derek Jeter in 2010).

Unfortunately, there is nothing that indicates that Cashman will lose his job anytime soon. Owner Hal Steinbrenner is too loyal to Cashman due to the team’s past success and their current status as perennial contenders. Even as the contender status slips away, the Yankees are so profitable that Hal can continue to make a killing while he and Cashman make false promises of a World Series champion to the fanbase. (Hal’s problems are a story for another time.)

Cashman’s insistence of building the team by his rules have effectively turned the Yankees into the modern-day Angels, boasting two incredible talents at the top of their game but failing to build around them properly. The fans can only watch in horror as Aaron Judge looks to suffer the same unfortunate fate as fellow Yankee captain Don Mattingly.

But in a hypothetical scenario, imagine if Hal has seen enough from the Yankees’ current squad and decides to rebuild. Would you trust Cashman to build a World Series winner?

For me, the answer is no.