yankees fire cashman
Brad Penner | USA TODAY Sports

Whatever general manager Brian Cashman’s plan was for the 2023 New York Yankees, it has failed worse than anyone could have imagined. Actually, following Wednesday’s series loss to the White Sox, it might be his worst failure yet in 25 years on the job.

Failure is a big word for someone who not only has been on the job that long, but has never built a team that’s suffered a losing season. Even now, the last-place Yankees are somehow three games over .500 and haven’t finished under since 1992.

So what makes the 2023 season stand out? How does this lost disappointment of a season compare to every other year without a World Series? Why is Cashman solely in #YankeesTwitter’s crosshairs this time when social media has existed for over a decade?

The answer is easy, Yankees fans. Unlike previous years, Brian Cashman does not have the Steinbrenner brass breathing down his neck 24/7. Anyone who remembers the days of George Steinbrenner policing the halls of Yankee Stadium knows this is atypical.

But in fact, looking back at what we consider Cashman’s greatest failures over time, the late Steinbrenner’s fingerprints are all over them. The Yankees grossly overpaid two gross overachievers in Jaret Wright and Carl Pavano before the 2005 season because they’d unknowingly gutted their farm system of top arms. The two managed one full season between them in four years, and Wright was only there for two.

And yet, even then, the Yankees rallied to win the AL East on the last day of the season.

Cut to 2008, when the Yankees miss the playoffs outright thanks to an aging roster. However, this is also when Cashman sort of set the tone for how he builds teams now. Note how despite streaky hitting, the Yankees have always managed to keep pitching competitive? This was the plan in 2008, except the trio of Phil Hughes, Ian Kennedy, and Joba Chamberlain didn’t pan out.

And the non-playoff years of 2013 and ’14? Simple. Even though George died in 2010, his closest advisors largely ran baseball ops for a few years after. Aging veterans like Brian McCann, Jacoby Ellsbury, and Carlos Beltran were overpaid in free agency just to field a competitive team. Cashman has even said that around this time, he was pushing a rebuild and was met with resistance from Hal Steinbrenner himself.

Not anymore. Brian Cashman has full run of the Yankees’ front office and Hal weighs in as needed. He’s already said his GM’s job is safe. The jury is out on manager Aaron Boone, as of now.

It still doesn’t take away from the fact that everything that has gone wrong with the 2023 season lies solely at his feet. This isn’t to say he’s at fault for the injuries. Brian Cashman didn’t make Aaron Judge run through a Dodger Stadium bullpen fence. Nor is he why Carlos Rodon has been a bust or the lineup hasn’t performed.

He did, however, pay these players and also added guys like Harrison Bader knowing all about their lengthy injury histories. He just decided they were worth the risk and that the Yankees could win with them. Just like how they made the ALCS last year, they would make it back in 2023 and win it all.

Nobody expected this unpleasant surprise. There’ll be no repeat MVP season for Judge. Giancarlo Stanton’s pricey decline continues. Don’t even mention Josh Donaldson. It took two months of Anthony Rizzo not hitting for the training staff to realize he was dealing with post-concussion symptoms.

Throw in DJ LeMahieu being a shell of himself, and the Yankees’ only real positive is Gerrit Cole making a strong case for the AL Cy Young.

It all adds up to the 2023 season truly being Brian Cashman’s worst failure as an executive. The Yankees have stumbled into the playoffs before, but at least had one strong stretch of season leading up to them. This year, they’ve done nothing but play catch-up since Opening Day. Losing a series to the lowly White Sox is just the latest bad mark on a worse year.

The saddest part is as bad as this looks for Cashman, the Yankees still look good on paper. The 2023 season has just been an abject failure in execution to the point of pure absurdity. Fans are frustrated because the team should be competitive. It just simply isn’t and losing to teams willing to go all-in on youth instead of overdeveloping them in the minors.

At the end of the day, Brian Cashman is a smart GM and he’ll try to chart a path forward for 2024. Fans won’t like it but it’s the same paradox as Aaron Judge’s free agency. Name someone else who can do the job better. It’s almost frustrating how someone seemingly so incompetent can also be so good at the hard parts of running a front office.

At best, maybe this year really was a fluke. Perhaps the Yankees get healthy in 2024, make some roster changes, and win it all.

Otherwise, we can expect more of the same. Brian Cashman sticks to his analytical guns and digs in his heels on the Yankee Way. And the fans perpetually weep.


Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.