15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
New York Yankees v Toronto Blue Jays / Abelimages/GettyImages
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11. July 31, 2017: Yankees Acquire Sonny Gray for Jorge Mateo, James Kaprielian, Dustin Fowler

The process was sound! The practice led to 45,000 fans booing a smiling man, teeth gleaming as he left the mound after getting lambasted by the last-place Orioles. Pretty bad practice.

At the very least, if not for Sonny Gray, the Yankees may never have ended up with Matt Blake, instead sitting out the drudgery of the Larry Rothschild Era for a few more seasons.

Gray was the pitching prize of the 2017 trade deadline (well, at least he was before everyone figured out Justin Verlander was also available at the end of the next month), but we probably should've realized this was all going to go sideways when the righty chose "Pickles" as the nickname on the back of his Players Weekend jersey.

The ex-A's starter was serviceable, not great in '17, posting a 3.72 ERA in 11 starts with 59 Ks and 55 hits allowed in 65.1 innings. Revisionist history says he was a disaster from the start, and his five one-hit innings in Game 4 of the ALCS against Houston can't be ignored. Still, the Yankees were hoping for an ace, and they got a No. 3/4.

The next season, things went off the rails. Gray posted a "get me out of here" 4.90 ERA and found himself routinely booed by the unforgiving public; he was dumped to Cincinnati the next offseason. The pieces the Yankees surrendered didn't really sting (Volpe, Peraza > Mateo), but this was still emblematic of another deadline whiff for the impact it was supposed to bring.