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.