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

New York Yankees general manager Brian Cashman might seem like he has it easy, but his job should be much less stressful. If the team spent the money they were supposed to, he wouldn’t have to focus so much of his energy on conducting financial gymnastics and adding to the roster via the trade market as much as he does.

Though it sounds like many fans are being brats when they’re asking Hal Steinbrenner to drop an extra $25-$30 million, it’s really not that tall of an ask in the biggest market in possibly the world and with the amount of money the organization charges its supporters.

Throw in the ostensible reality that New York faces a “Yankees tax” on the trade market since every other team is fearful of making them better or losing a trade to them (see: Mets), and the task is even tougher.

That’s why Cashman definitely needs more credit for the trades he sometimes doesn’t make. Time and time again, teams have tried to rip him off for players that weren’t worth the asking price.

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That’s why he’s had to perfectly craft trade packages to minimize risk more times than not. Though it’s a frustrating practice, sometimes there’s no other option, because depleting your farm system and not utilizing your spending power cannot happen in unison.

So here’s a Cashman appreciation post on how, deep down, we do appreciate him being able to read the trade market better than most.

Yankees: The three best trades Brian Cashman didn’t make in recent years.

3. Avoiding Robbie Ray Back in 2019

Though Ray might’ve helped given the exhausted/skeleton crew starting rotation in the 2019 ALCS, he was still a 4.00+ ERA pitcher and the Arizona Diamondbacks were looking for a king’s ransom in return.

Don’t believe us? This is from D-Backs insider Nick Piecoro from a couple years ago:

“The club entered the day widely expected to move left-hander Robbie Ray; sources with multiple clubs said the Diamondbacks’ asking price on Ray was extremely high, with one describing it as ‘crazy.'”

Forget about Ray’s 2021 Cy Young-winning season, because the Yankees would not have re-signed him after the way he performed in the second half of 2019 and during the shortened 2020. With Arizona in 2019, Ray closed out the season with a 5.56 ERA in his final 10 starts. He followed that up with a 6.62 ERA in 12 games (11 starts) with the D-Backs and Blue Jays in 2020. The Yankees had the option to sign Ray after 2020 and opted not to, and they certainly wouldn’t have done so after surrendering a haul to Arizona if this had happened.

He still has never thrown 200 more innings in a single season despite debuting in 2014. Good pass.

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).