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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14. Aug. 1, 2022: Yankees Trade Ken Waldichuk, JP Sears for 8 Frankie Montas Starts

The process was fine here. The Yankees had to go for it at 2022's deadline with a superior team to 2021's bunch, and there was no way they were trading Anthony Volpe for Luis Castillo, who ultimately went to the Mariners.

They also firmly believe they can print top-level pitching whenever they want to these days, and they remain unconcerned about the dearth of depth currently in the upper minors, assuming Will Warren and Drew Thorpe will join Matt Krook soon enough.

No matter how calculated the risk was at the time, though, it hasn't worked out. It has, in fact, bombed spectacularly. The process gets less sound when you recall Montas had a balky shoulder before he was traded, the medical team approved whatever was in there, and then he showed up with a cement mixer and had to be shut down again in September. It gets lowered another level by Montas' career ERA on the road, which sits at an unsightly 4.72. The Yankees believed that trend would reverse itself under their tutelage; Montas never got a chance to learn much.

Look for this trade to move up in next year's edition of this list, creating room for "Hayden Wesneski for Scott Effross."