Pablo Lopez-Gleyber Torres Trade, 2022
Of all the "close calls," this one might've been the closest.
America may never know whether Cashman actually believed this swap was done done and prematurely pulled the trigger on the Jordan Montgomery/Harrison Bader trade, believing he wasn't sacrificing any pitching at all. It's a logical story, though. All we know is that MLB insiders have confirmed this trade was quite close to being finalized, and reading about it threw Gleyber Torres off for the entire month of August, his worst as a Yankee.
Instead of adding Lopez and Frankie Montas at the deadline, the Yankees acquired only the injured Montas, who was good for eight ill-advised starts. Add the Andrew Benintendi wrist snap and Scott Effross' pre-postseason Tommy John, and you have one of the darkest timelines imaginable.
Lopez posted a 4.61 ERA last August himself, and probably wouldn't have been well-liked by those eternally-patient Yankee fans anyway.