Aaron Judge might be back in the fold, but that doesn’t mean the Yankees’ most complex — and potentially consequential — offseason in several years is close to over. The Judge negotiations would have been stressful enough without the palpable disappointment behind 2022’s second-half collapse and fourth straight playoff loss to Houston. It’s given this offseason a sense of urgency that’s not new but not common, either. It strikes some similarities to other critical roster shakeups during Brian Cashman’s recent tenure.
Let’s rewind to the beginning of the 2008-09 free agent period. That sense of urgency seems to have been profound after the Yankees missed the playoffs for the first time in a decade and a half, which itself followed three consecutive ALDS exits.