Yankees: 3 best trades (in recent years) Brian Cashman never made

2. Letting the Padres Overpay for Mike Clevinger

At the 2020 MLB trade deadline, the Yankees certainly needed help. But they didn’t need to deplete their farm system for a player who probably wasn’t going to be a fit, especially with the San Diego Padres acting like mad men and driving up the price for so many big names.

One in particular was Cleveland Indians starter Mike Clevinger, who, admittedly, is a pretty damn good pitcher! He’s got a career 3.14 ERA, 3.53 FIP, 141 ERA+ and 1.19 WHIP in 105 career games (92 starts). The Yankees really could’ve used that help behind Gerrit Cole in 2020, since we saw how that disastrous season unfolded.

But the Yankees dodged a bullet here. They were rumored to be interested in the right-hander, but the Padres swooped in and surrendered a combination of SIX players and prospects for Clevinger, outfielder Greg Allen and a player to be named later.

Then, four starts into his tenure with the Pads, Clevinger suffered an elbow injury and needed to undergo Tommy John surgery. He missed all of 2021 as a result and contributed just one inning of work in the team’s six postseason games in 2020.

Imagine what a nightmare it would have been if the Yankees’ 2020 playoff run and 2021 season had gotten derailed in such a manner? Though this was a situation largely characterized by “dodging a bullet,” the price was certainly prohibitive and Clevinger’s outspoken personality likely would have upset the apple cart in New York (not a bad thing! Just how the Yankees operate).