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Evaluating Yankees GM Brian Cashman

2022 was the first year one author lost confidence in the executive.

ALDS Game 3 - New York Yankees v Cleveland Guardians Photo by Nick Cammett/Diamond Images via Getty Images

The saying may be “victory has a thousand fathers, defeat is an orphan”, but there have been several potential parents for the blame of the Yankees’ 2022 season. Some people blame Aaron Boone, some Hal Steinbrenner, some the players themselves. All parties share some of the responsibility for a disappointing season, but I think that the primary patriarch of the outcome of this club is the guy who has near-free-reign to run it, Brian Cashman.

Yes, Hal Steinbrenner is the managing partner of the team of investors that actually owns Yankee Global Experiences LLC. This is still Brian Cashman’s team. After 25 years at the head of baseball operations, he has molded the organization into his own image. For the most part, this has worked out really well — the Yankees haven’t posted a losing record in my lifetime, they are consistently in the battle for the AL East title, and even when they’re bad, like in 2013 or 2014, they’re not bad the way that the Pirates or the Rockies are.

Yet this is the first year that I’ve been legitimately concerned at the decisions being made by the organization, and those decisions are made by Brian Cashman. The organizational pivot towards prioritizing defense didn’t come from Aaron Boone — Cashman was the one to take on $50 million in Josh Donaldson for those sweet, sweet web gems that Isiah Kiner-Falefa and Ben Rortvedt provided.

The trade for Frankie Montas, the big splash at the August deadline, was a complete nothingburger — and if he doesn’t have a strong 2023, maybe one of the all-time bad trades. Andrew Benintendi worked well on paper, but only had a short run of effectiveness sandwiched around being bad and being hurt. Some of the moves Cashman made worked! Lou Trivino was a nice pickup, and obviously Jose Trevino worked out extremely well — even if it only came after the Rortvedt trade and injury.

I think my criticism of Cashman is less about individual moves though, and more about policy, philosophy, direction. I don’t know who sets the “playoffs are a crapshoot” “spend but spread” ideology of the organization — I really don’t think Hal Steinbrenner is that involved in anything on the baseball side aside from setting the topline budget at the start of the year. I think that Hal is a businessman, not a baseball man; give him the credit for the partnership with Amazon and reacquisition of YES, not the 99 wins the team put up this season.

Brian Cashman is the baseball man, and it’s him who I’m going to primarily blame for the roster construction. I’ve never cared for the argument that he’s constrained by payroll decisions: first of all, I really do think that Cashman, who is incredibly self-confident, doesn’t mind the constraints. I think that he privately bristles at the idea that the Yankees buy their championships or that his job is easier than others because of his financial reach. I think he’s very happy to operate under imposed payroll: if he wasn’t, he would have left by now.

Therefore, when Aaron Boone says things like the league has “closed the gap” on the Yankees, and you’re the guy in charge of the roster, and the roster reflects that said gap is still closed — you were dumped by the same team for the fourth time in eight years — I think you shoulder the blame, and I think this is the first year that I’ve questioned whether or not Cashman is the right guy to lead the baseball side of the organization.

Whether Aaron Judge comes back or not, he’s not going to have an 11 win season. Even if he’s really good next year, seven or eight wins, do you trust the roster as it stands to be better than 99 wins? Do you trust that the Yankees will make significant moves, aside from calling up Anthony Volpe at some point in 2023, to try and re-widen the gap that’s closed?

I don’t know who the replacement would be. Anyone from Cashman’s team, after 25 years of near-total control over baseball ops, would be an extension of Cashman’s beliefs and approach. There are folks who I’d like to see in the Yankees front office — Jason Paré from Atlanta and Sarah Gelles from the Astros immediately come to mind — but I don’t think the Yankees are willing to undergo a radical transformation of the brain trust.

Steinbrenner’s already signaled that the team is going to work out a new contract for Cashman, and the symbiotic relationship between the two continues. Hal is happy with this arrangement, and Cashman is, too. I don’t trust the team to make a serious change of direction or philosophy, and I don’t think Cashman sees the need for one. I wonder what it would take for him to get there.