Evaluating Yankees GM Brian Cashman

The Yankees really are Brian Cashman’s team. By far the longest serving GM in the game, he’s as synonymous with this era of Yankee baseball as Billy Beane is with the Athletics. His crowning achievements — the 2009 World Series, and the on-the-fly rebuild of the team in 2016 and 2017 — and building a consistent playoff contender have likely moved him into a position where he’ll be the GM for as long as he wants to, but after two straight seasons of a depreciating roster, his decisions deserve scrutiny.

Cashman made a series of bets last winter, trading for Jameson Taillon, signing Corey Kluber, and setting a “revolving door” of a starting rotation, with six or seven different potential arms behind ace Gerrit Cole. To his credit, the starting rotation was stronger than a lot of us thought it would be, finishing sixth in fWAR and top-10 in ERA, FIP, and posting the fifth best K-BB% in baseball.

Kluber and Taillon combined to throw 224.1 innings, but only 80 of those came from the Klubot, who struggled to rediscover his command after returning from injury, and Taillon very clearly struggled with the added workload down the stretch after so much time on the shelf the last two seasons. Deivi García was a disaster in both the majors and minors, cutting away a chunk of the projected depth.

Jordan Montgomery and Néstor Cortes Jr. took major steps forward this season, and while I think Matt Blake does deserve the lion’s share of credit for their development, Brian Cashman hired Matt Blake. I don’t necessarily know how much the club expected out of Cortes, but it’s entirely possible that the team’s internal metrics or projections pegged Monty for a bigger role in 2021 than he’d shouldered before, and that went into offseason strategy.

Cashman also did a lot to improve the team at the trade deadline, acquiring Anthony Rizzo, Joey Gallo, Joely Rodríguez and Clay Holmes in a pretty wild couple of days. Holmes was perhaps the most valuable of the foursome, immediately thrust into high leverage slots in the bullpen. Joey Gallo was a disappointment, although having him for next season as well mitigates some of that risk. Anthony Rizzo was solid at the plate, great in the field, supposedly wants $100 million as a free agent and I have a hard time imagining the Yankees would give him that.

But I think when we talk about Brian Cashman, getting lost in one acquisition or another can get you a little lost. The level of control he exercises over the roster and organization merits a broader discussion about the things he values, the pieces that he thinks builds a winning team — and critically, the projections that fuel the acquisition and retention of those players.

We don’t know what internal projections the Yankees have, but when we look at something like ZiPS, Gleyber Torres was supposed to be the best player on this team. DJ LeMahieu was pegged for a 117 wRC+ season. It’s safe to say, based on the way the team kept running out both players despite significant setbacks, that whatever projections the club runs roughly agreed with ZiPS, that these players Should Have Been Better. This also applies to Joey Gallo’s projected Yankee performance — they batted him cleanup in the Wild Card Game because he Should Have Been Better than he was.

And this is my biggest criticism of Cashman’s tenure: The fear that the metrics and projections the team relies on are not as accurate as they could be, or that they value the wrong things. The Yankees still maintain, for example, an offensive philosophy of working counts, wearing down the starter, which is actually in contrast to some of the other top offenses in the game, like the Blue Jays and Astros, who are much more aggressive early in the count.

Like I wrote about over the summer, the critiques of Cashman revolve around the data he uses to build the roster, and how robust the testing and feedback loops around the data is. The team can be slow to change — see DJ LeMahieu stuck in the leadoff spot all year — and while this is likely due to organizational faith in their internal projections, and the importance of large samples, it can create problems with urgency. You can wait around for more data on your DJ projection when you have a six- or seven-game lead in the division, you can’t really do that when you’re fighting tooth and nail for a Wild Card slot.

I don’t think Brian Cashman is going anywhere this winter, and while his contract is up next year, I don’t think he would leave this organization on anything other than his own terms. He is as much a Yankee institution at this point as any player has ever been. Any significant change in Yankee philosophy probably has to come from Cashman re-evaluating the things he thinks are valuable in roster construction and performance, rather than restructuring the decision makers.

Editor’s note: Due to the chaotic schedule and end-of-season madness, we didn’t see much of a point of running an end-of-month poll in September on Cashman’s approval, like we did throughout the season. However, if you’d like to vote on an end-of-season poll for him, do so below.