Brian Cashman
Kim Klement | USA TODAY Sports

It’s important to preface this piece with the following: Brian Cashman is all but certainly coming back to the New York Yankees in 2023.

What far too few have the cojones to say is the obvious opposite: Brian Cashman’s time with the New York Yankees needs to end regardless of result. The Cleveland Guardians could end the ALDS tonight or New York could win the rest of the way to World Series No. 28. Even then, 25 years on the job will have been too long for the veteran Yankees general manager.

It’s just becoming too much. The obsession with analytics and value at the expense of signing clear needs from the free agency market. The brusque politicking during press conferences.

None of this is to say Brian Cashman has done a bad job building successful Yankees teams. When the Yankees had no choice but to land Gerrit Cole in free agency, he went and got him. Without Brian Cashman, there is no Nestor Cortes, no All-Star seasons from Jose Trevino and Clay Holmes.

This is the success Brian Cashman has had with the New York Yankees in the last decade. Not so much with winning championships, but with sneaky good acquisitions and player development. His system always seems to have the Yankees in contention year after year.

And yet, this writer is willing to risk all of that going down the tubes because of one key mistake from Saturday night. Let’s revisit:

The Yankees led the Guardians 5-3 with one out in the bottom of the ninth inning of Game 3 of the ALDS on Saturday. Wandy Peralta, in his second full inning of work, then allowed back-to-back singles to Myles Straw and Steven Kwan. Instead of handing the ball to All-Star closer Clay Holmes, manager Aaron Boone rolled with rookie Clarke Schmidt.

Schmidt did get Josh Naylor to strike out for out number two, but the damage was done. He loaded the bases first and then gave up a walk-off single to Oscar Gonzalez and the Guardians won 6-5.

First, there are so many things wrong with this from a baseball perspective. Keeping Peralta in the game was fine, but there should have at least been someone warming just in case. Since Schmidt is a starter who takes longer to get ready, he should have been throwing in the top of the ninth rather than warming up quickly once Peralta was already in trouble. His meltdown was practically inevitable.

Plus, where was Holmes? Boone said his All-Star closer was sore and only available in an emergency. Someone clearly didn’t tell Holmes, who made very clear he was available to pitch. Luis Severino, who started Game 3 and was in line for the win, was also shocked.

Now, at first glance, this looks like a glaring miscommunication from Boone. He easily could have been covering his own mistake by saying Holmes, who threw 16 pitches on Friday, was unavailable to do back-to-backs. This would be understandable, given his injuries this season and possibly being needed if Gerrit Cole wasn’t overly dominant in Game 4.

Except knowing Boone, that’s probably not the case. His players defend him to the death, even through the worst of times. Sure, he should have owned his mistake last night, but what if it wasn’t actually his?

What if losing Game 3 was due to exactly what all Yankees fans fear? As in, the longstanding rumor that Brian Cashman and his analytics team are always dugout adjacent during games and influence decision-making. There’s no confirmation of this, but there have been enough questionable decisions over time that it’s clear the numbers have influence over instinct.

Cashman’s reach doesn’t just extend to in-game decisions either. Jordan Montgomery was popular with fans and teammates, but was unceremoniously traded to the Cardinals when there was suddenly no further use for him. St. Louis then did what the Yankees never did and encouraged him to actually throw a fastball.

Naturally, Montgomery had some choice words on the matter too. For someone who dismissed his last manager for “connectivity and communication issues,” Brian Cashman doesn’t seem to be much better at it.

Was it Boone or Cashman’s mistake in Game 3? Perhaps we’ll never know, but this way of doing business is getting old and tired. Just like 55-year-old Brian Cashman.

It’s been the same cycle for years. Build a team with players and ride everyone out until the numbers deem them useless. Sure, it generally works, but should it be the end-all and be-all of whether the Yankees win or lose games? There’s definitely utility to analytics but a sport doesn’t last for over a century without instincts playing a role too.

Again, Brian Cashman has overall done a good job running the New York Yankees. Some might even say a great one. We know where he’s succeeded and where he’s failed.

But if the goal in New York is to win a World Series every year, then it’s time to move on. It’s been over ten years since winning a World Series and, as the Captain himself Derek Jeter said, “the fans boo because they want to cheer.”

When push comes to shove, Brian Cashman is a smart guy. He bit the bullet and let Joe Girardi go after 2017 despite the Yankees finishing just a win away from the AL Pennant. He knew that record aside, a new voice was needed.

It’s time for him to use that big, analytics-ridden brain of his and come to the same realization. Only this time, Cashman will have to accept a hard truth.

He and his philosophy are the problem, and more and more to the detriment of the New York Yankees. But hey, what’s another five-year contract if the system works just enough, right?

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.