MLB trade grades: Yankees fleece Pirates in Jameson Taillon deal

MLB Hot Stove, New York Yankees, Pittsburgh Pirates

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The Yankees took a calculated risk by trading for Jameson Taillon, but the price they paid the Pirates was shockingly low. 

There’s a decent chance that Jameson Taillon’s checkered injury history will prevent him from becoming the impact pitcher the Yankees hope he will be. It’s still impossible to describe this trade as anything other than a clear and decisive victory for Brian Cashman and his front office.

The Yankees sent four prospects to Pittsburgh in the deal. Miguel Yajure is a young reliever who might be advanced enough to help the Pirates right away. Roansy Contreras is a decent lottery ticket as a prospect, but he’s nowhere near ready to be an impact major leaguer. Canaan Smith is also a top-30 prospect with a good bat overall, but his other tools could use some work.

The other player in the deal failed to crack New York’s list of top-30 prospects per MLB.com. Maikel Escotto doesn’t project to be a meaningful loss for the Yankees anytime soon, but does have some upside.

The Pirates are only giving up Taillon in the deal and they clearly are banking on the possibility that he won’t bounce back from the Tommy John surgery that cost him all of 2020. New York envisions him as the ideal veteran with upside to slot in behind Gerrit Cole and Corey Kluber atop their 2021 rotation.

Yankees Grade: A

The fact that Taillon is only slated to make $2.25 million this season pushes the transaction to an A. That’s a massive bargain if the 29-year-old pitches anywhere close to his 2018 numbers which saw him go 14-10 with a 3.20 ERA in 191 innings.

His acquisition allows the Yankees to achieve their stated goal of staying below the luxury tax in 2021. Consider it a bonus that Taillon has one more year of team control before he hits free agency.

His injury issues are a definite concern for the Yankees, but there just isn’t any meaningful downside to this acquisition. The team parted with a few interesting prospects, but they needed to clear room on their 40-man roster to make room for their new acquisitions. Not giving up a top-10 prospect or a current major leaguer was a big victory for New York.

Pirates Grade: D+

It may seem harsh, but this trade is inept from Pittsburgh’s point of view. They gave up a pitcher with a chance to be an above-average regular for four relatively anonymous prospects.

The most salient question to ask here is why the Pirates were in such a hurry. They easily could have held on to Taillon until closer to Opening Day to see if they could get a better offer. There was no reason to rush to deal him in January.

At worst, Pittsburgh could have allowed Taillon to start the regular season with the team. A few good outings could have driven his trade value up considerably. Instead, they chose to sell him when his value was arguably at its lowest point.

Yajure is the team’s best chance of salvaging this deal in the long run. He’s got swing-and-miss stuff that gives him a chance to become an above-average regular. That’s not enough upside to justify offloading a quality starter under team control. The Pirates needed organizational depth, and they got it. But had they simply waited a little longer, they could have made more of an impact on a farm system that very much needs some upgrades.

It’s tough to know exactly how a deal will look five years from now with so many prospects involved, but the Pirates are essentially taking on some fliers. Taillon ought to be worth more than that, even if he’s injury prone.

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