Manny Machado, 2018-19 offseason
Noticing a theme here? The year the Yankees really should've gone for it, especially after being kicked in the teeth unexpectedly by the 108-win Red Sox, they instead took another middling step forward financially. They traded prospect depth for James Paxton. They signed Adam Ottavino and extended Zack Britton. They paid JA Happ. They managed to steal DJ LeMahieu (good!), but used the rest of their cash to get out ahead of things and extend Luis Severino and Aaron Hicks unnecessarily (so, so bad!).
And, meanwhile, they let a pair of generational talents wait around all winter, then make exciting new homes elsewhere (we'll get to the other guy by the end of this list).
Those four months in 2019 where fans got to compare Gio Urshela's juiced ball stats to Machado's were fun, but the Padres got an all-timer here, and the Yankees didn't entertain the notion of signing him, even as his value slipped throughout the winter. They were, at one point, considered the favorites for his services. But when you've got Miguel Andújar holding down the position, it's certainly risky to pounce! Whew, boy. Machado paired OPS+ marks of 110, 160, 131, 157 and 113 in San Diego with exceptional defense. The Yankes have Josh Donaldson on the 60-Day IL.