Part 5/12:
The failure to re-sign Andrew Benintendi after a promising start was another source of disappointment. They assumed they could figure out left field later, resorting to starting Oswaldo Cabrera on opening day, which proved to be a poor choice. Benintendi’s subsequent struggles in Kansas City or Chicago further underscore how misjudging talent and timing can set a team back.
The Grand Sin: Not DFA’ing DJ LeMahieu
Perhaps the most emblematic mistake discussed was the Yankees’ reluctance to DFA DJ LeMahieu in recent offseasons. They held onto him despite performance declines, missing out on roster flexibility and potential upgrades. This inability to cut bait reflects a broader issue of sticking with expensive veterans long past their prime.