Brian Cashman, like his boss, is not a risk-taker. Even so, what are the chances he would voluntarily step down as the Yankees GM?
Brian Cashman’s Yankees give little or no indication they are in a position to revive themselves from what can only be considered a disastrous showing this season, one that was supposed to take them to a meeting with the Dodgers in the World Series.
Forgetting that, and I know it’s a tough nut for Yankees fans to swallow, the real question before the Yankees is their future, specifically those at the top of the Yankees organization.
Exclude Hal Steinbrenner and his family because, like the Wilpon’s and the Mets, they will only cede power and influence when they are (financially) forced to, and that is not likely to happen in our lifetime.
The Brian Cashman Legacy
Brian Cashman is another matter, though, for those seeking real change in the Yankees’ organization.
While we can only hold our breath waiting for Steinbrenner to give a damn about his team, Cashman is another matter.
For one thing, while his legacy is already intact as the longest-tenured Yankees’ GM in their history, and he can lay claim to five World Championship titles during his reign, plus recognition by from his peers as the GM of the Year in 2017, Yankees fans know that was moons ago.
There’s zero chance the impotent “Boss” of the Yankees, Hal Steinbrenner, would fire Cashman in retaliation for the roster he presented to Yankees’ manager Aaron Boone this year. So instead, Cashman stands alone, safe in his job for as long as he wants it.
It comes down to what Brian Cashman wants to with the rest of his professional career and life at 53 years of age.
Brian Cashman Versus Theo Epstein

We already have seen one of his peers, Theo Epstein, step down from a prestigious job with the Chicago Cubs after bringing the first World Title to the Cubs in umpteen years in 2015.
Epstein’s belief at the time was the Cubs were entering a rebuilding phase he didn’t wish to be a part of, and while at the time his prediction was generally accepted by nearly everyone, here are the Cubbies leading the NL Central today and threatening to run away from all their competitors.
If Brian Cashman were to make the same judgment as Epstein did about the Cubs, chances are nil he would have the energy and desire to do the trench work necessary to rebuild the Yankees.
Obviously, that decision by Cashman rests solely on his assessment of the current team and its future. Any honest evaluation would tell him it’s time to get out of Dodge – now!
If Cashman Was To Step Down…
If he were to do that, the choices for Brian Cashman are two-fold, and neither of them is all that bad.

Cashman can resign to take a post in the hierarchy of the Yankee’s organization as his just rewards for a job well done and one that would be bequeathed gladly by Hal Steinbrenner.
Or, he can pursue a career as an analyst for ESPN, FOX, or the already crowded booth at YES, a cush job that will pay him well, requiring little or no effort on his part.
Neither seems a fit for the oversized ego of Brian Cashman, who thinks nothing of drawing attention to himself by propelling down from a New York City skyscraper or sleeping with the homeless on the streets of New York.
Back To The Epstein Model…
What’s left is for Brian Cashman, if it’s within his “soul,” is to tackle another job, this time with a medium to a small-market team for one last hurrah that brings a Championship to a team that hasn’t seen one in decades. (think Cincinnati, Pittsburgh, Milwaukee, etc.)
Following the Theo Epstein model and assuming Cashman has the same luck as his peer, he would then be able to write his own ticket as the next, and perhaps the final step in his career.
Epstein, for example, now works in the commissioner’s office as a consultant regarding on-field matters.
I would like to think Brian Cashman wants that one last hurrah and that he sees separating himself from the Yankees as the sole way to achieve another championship.

But in the end, Brian Cashman impresses me as a go-along to get along type of person who lucked into a situation with the Yankees that had gold written all over it.
He made the best of it to his credit in that he did not screw up anything when he inherited the GM position, letting it play out to his advantage.
But given the baseball axiom of “what have you done for me lately,” he has failed miserably.
We can sit here to recount the numerous trades Brian Cashman has made over the years, good and bad, but the singular matter that stings in the craw of Yankees fans is the eleven-year drought between now and the last Yankees Championship that occurred way back in 2009.
Brian Cashman’s Assessment Of The Yankees

This brings us back full circle to this question. Does Brian Cashman believe, as he looks down the Yankees roster and the players in their farm system, that the Yankees have the wherewithal to win a World Title with what they have now?
Moreover, does he believe the tightening of the purse strings on Yankee’s payroll is a “let’s see if you can do it”challenge, or is this the mindset etched in stone by Hal Steinbrenner, come hell or high water?
My feeling and I hate to say this as a fan of the Yankees for more than a half-century, is that neither scenario matters because Brian Cashman only sees Brian Cashman in his or anyone else’s future.
Brian Cashman Is Not A Risk-Taker
He is not a risk-taker like Theo Epstein.
I know full well that is a condemning statement, and I don’t make it offhandedly.
But you can bet your bottom dollar that Brian Cashman will ride this thing out along with his puppeteer Hal Steinbrenner until both are unceremoniously run out of town, a la the Wilpons years from now, and it won’t be until they are good and ready to do so.
So, where you might ask, does that leave the Yankees fan today?
It depends because when all is said and done by the powers that be, including Brian Cashman, it’s the 26 players who suit up every night wearing the pinstripes who have the opportunity to carry the Yankees’ legacy forward.
We have our doubts about this Yankees team, and they are well-founded.
Most likely, and Yankees fans will not like this, is that Brian Cashman will make a disingenuous stab at trades before or at the July deadline to improve the team like he did last year, only to emerge from the process saying the “price was too steep to pay” to do anything significant.
The Simon And Garfunkel Duo Of Baseball
The pairing of Hal Steinbrenner and Brian Cashman is as harmonious as Simon and Garfunkel, a match made in heaven.
However, unlike the singing duo that split to take on new challenges by carving out new career paths, the Hal and Brian team appears to be content pumping out medium-sized hits, one after another, and playing as the opening act in sold-out arenas.
A Yankees fan, I’ll always be, but this scenario is particularly punishing.
Here’s What Readers Are Saying…
Ronnie Zimmerman Trade time is now. Before other teams beat you to the players u want
Robert Michael Mcfee Looks like the Tampa equation is working
David Paseornek Zero Steve Contursi Look, unless Cashman is given the option to resign or to be fired he won’t be stepping down
Rich Sobik Why would he step down? His hands are tied since Hal doesn’t want to go over the cap and doesn’t wanna trade anyone. Cashman gave the Yankees an all-star team on paper It’s not his fault they’re not playing good ball
AJ Torres He was. When Didi got here we ripped him. Wilson for Green and Cessa we hated it. He does take risks. Hal is a bum. He doesn’t get it
Stephen Guardino Zero chance Cashman steps down voluntarily and close to zero chance that Hal fires him. Unfortunately, Hal is nothing like George.
Bruce Kain Not quite sure how Cashman has “failed.” His job is to put a capable team on the field and he has done just that. Las Vegas had the Yankees favored to win the AL Pennant with the 2021 team he assembled. Blame underachieving players, blame an inexperienced manager, but Cashman did HIS job. Who DIDN’T think this team was a serious contender?
Ken Walter He won’t leave until he is fired. His salary must be astronomical. He has been riding the gravy train for way too long. Steinbrenner needs to grow and fire this guy.
Leon Fermin Voluntariamente no va a renunciar y por la fuerza, lo dudo; es esposo de una de los dueños; pero creo que es hora ya de salir de él, del equipo médico y del dirigente
Don Salvatore What is it going to take for Hal Steinbrenner to finally say enough is enough and make changes. I guess having the worst Yankees team in 50 years is not it.
Ray Palen I fear it is already too late to turn things around. Tampa, Boston, and Toronto are too good to all collapse at this point and Baltimore keeps getting better! Scary times for NYY fans!!!
Regretfully and due only to volume, I’m closing off published comments for this post. Keep ‘em coming though – after all – that’s what this is all about.