Evaluating Yankees GM Brian Cashman

Brian Cashman has been in charge of the Yankees’ on-field product for more than 20 years, and on the aggregate, is one of the more successful executives in modern baseball history. He overhauled an aging and expensive roster, ushering in the Baby Bomber era, and oversaw a chaotic 2020 while fielding a relatively older, more expensive roster, all while refusing to push in any trade chips or take on additional payroll for the second consecutive year.

It’s hard to just give a single grade to Cashman. In spring training, we were coming off the biggest free-agent pitcher signing in MLB history, as the Yankees’ GM pulled out all the stops in landing Gerrit Cole. The top of the Yankees’ roster was as good as any in baseball, and the team was a popular World Series pick.

If the team had a weakness, it manifested in the pitching depth. Cole, Luis Severino, and James Paxton were as good a top three as you could find, but if something happened to them, the lack of additional signings presented a challenge.

Well, you’ll never guess what happened.

I don’t blame Cashman for injuries to pitchers; anyone’s UCL can burst at any time, and pitching injuries were at an all-time high across the game this year. What I do blame Cashman for is not supplanting that top-heavy pitching staff with better depth, especially during the season.

Getting Lance Lynn makes that weird ALDS Game Two decision a lot easier, doesn’t it? You just hand the ball from one top-five starter in baseball to another, instead of whatever that weird pseudo-opener strategy was. Trading for Archie Bradley means you can trust more than just Aroldis Chapman and Zack Britton in a playoff series. The team has the money, and if this is the window, the potential wins in 2022 and 2023 represented by prospects in the system matter a whole lot less.

And here lies my central criticism of Cashman. He consistently builds excellent rosters, and the analytical team he’s constructed puts together strong, logical game-plans. But he has no flexibility. If everybody has a plan until they get punched in the mouth, Cashman’s teeth have been on the mat for three years, and he’s been unable to re-adjust.

This inflexibility doesn’t just affect the team at the trade deadline. Like the Dodgers, the Yankees make a lot of in-game and lineup decisions by committee, with Cashman at the head of the table. If Cashman wanted Giancarlo Stanton in the outfield, he would have played an inning there in the postseason, even in cases where there was a real advantage to loading the lineup a certain way. Ditto for Clint Frazier. Cashman’s loyalty to Brett Gardner has left runs on the table, especially in 2020.

Of course we’ve seen this in how Cashman negotiates with free agents as well, often adapting a single-offer, take-it-or-leave-it approach. He’s done this to guys from Robinson Canó to Patrick Corbin, and while you might be able to accept one of these moves, the pattern makes for concern. Past is prologue, and now the exact same strategy is being bandied about as the Yankees decide what to do with DJ LeMahieu.

And yet, despite all this, the Yankees were a run away from advancing to the ALCS, and depending on what they do with Mr. LeMahieu, will enter 2021 as one of the most talented teams in baseball. Cole isn’t going anywhere. Aaron Judge, Luke Voit, Gleyber Torres, Gio Urshela, Frazier and Stanton still form one of the best offensive cores you could hope for - and two of those players are among the all-time great front office decisions, as Cashman’s staff was able to identify and improve Voit and Urshela for peanuts.

It’s hard to evaluate Brian Cashman. He consistently builds strong and talented rosters, while consistently showing a lack of flexibility as things go wrong. There aren’t many GMs I’d rather have at the helm, but there are very real flaws in his leadership, and a very real chance he whiffs on winning a championship with one of the most talented cores in baseball.