The most powerful person within the most powerful baseball team on earth is a thin, bald, bespectacled, 5-foot-7 man who grew up on a horse farm in Kentucky. Hollywood turned to Brad Pitt to portray longtime A’s executive Billy Beane. Jason Alexander (who has a Yankees connection anyway) might be the better match for Brian Cashman.
In an era in which the faces of baseball teams’ operations departments are Ivy League-educated, formal and highly skilled at saying little — with lexicons that are heavy on sustainability and predictive modeling — Cashman played baseball at Catholic University, graduated and essentially earned his masters at George Steinbrenner University. If you can make it there, you can make it anywhere.
The voice of the Yankees speaks like, well, a human. Cashman labeled the 2023 Yankees season a “disaster.” Months later, amid an endless barrage of arrows slung against him and anyone in pinstripes, Cashman said the Yankees’ processes “are pretty f–king good.” And no, he does not have any regrets about that news conference and his fiery defense of the organization.
There are a few who arguably could come close, but Cashman does not have a peer. He is the longest-tenured lead decision-maker in MLB by about a decade and the longest in Yankees history. (Cashman started in ’98, John Mozeliak with the Cardinals in November 2007.)
