Ranking Brian Cashman's worst pitching trades for Yankees

We had some time to cool off after the Frankie Montas shoulder surgery news, which marks another sunk cost in a long line of them for the New York Yankees. The right-hander will likely finish his time in the Bronx making just eight starts over a year and a half after an injury that was well-documented prior to the trade at least year's deadline ended up hindering him in 2022 and knocking him out for most (if not all) of 2023.

Unfortunately, this has become an all-too-familiar narrative for the Yankees under general manager Brian Cashman, who has continued to whiff on most trades concerning pitchers (chiefly starters). Loyal fans will point to his acquisitions of Luis Cessa and Chad Green back in 2016, Tommy Kahnle and Michael King back 2017, and more recently guys like Clay Holmes, Wandy Peralta and Lou Trivino ... but that's not enough to win a World Series. It's a good start, but that's about it.

Had two of these gone the Yankees' way, we're singing a completely different tune. But the vast majority of the misses have been catastrophic, and we'll relive the pain after Montas' injury sent the Yankees from "best rotation in baseball" to "we have no idea who the fifth starter will be for all of 2023." Fun times.

Ranking Brian Cashman's worst pitching trades for the New York Yankees

2015: Aroldis Chapman

It sure does seem harsh to put Aroldis Chapman on this list because he finished his Yankees career with a 2.94 ERA, 2.89 FIP, 1.15 WHIP, 453 strikeouts and 153 saves across 315 games (294.1 innings). BUT ... the Yankees traded for him under shady circumstances (he was under investigation for domestic violence), directly played a part in ruining three postseason runs (2017, 2019, 2020), and was signed to an unforgivable contract extension after blowing the 2019 ALCS.

Had the Yankees let Chapman depart after 2019 following an opt out, Yankees fans probably have no ill will. But those extra three years and $48 million left everyone with a sour taste in their mouths, especially with how he performed in 2022 (prior to ditching the team for the postseason because he wasn't guaranteed an ALDS roster spot).

And by the way ... who gets a tattoo infection in the middle of a division race?