Ben Cherington's horrible history with Yankees should give Pirates fans trade deadline anxiety

Ben Cherington's Pirates regime has struggled to change the franchise's trajectory, primarily in the trade department. After selling a ton of pieces from 2020-2023, only a handful of his acquisitions have made the major leagues, let alone made a positive impact in Pittsburgh. One team in particular that has seemed to always win trades with Cherington has been the Yankees, and recent rumors suggest another one could be approaching.

Jon Heyman of the New York Post recently reported that the "Yankees have been in regular contact with the Pirates." He noted that Pittsburgh has a couple of notable players that would interest New York, including Ke'Bryan Hayes, David Bednar, Dennis Santana, Isiah Kiner-Falefa, and Mitch Keller.

The interest from the Yankees regarding Hayes and Kiner-Falefa has been around for weeks, and it wasn't until a few days ago that Keller's name was brought up, too. Pirates insider John Perrotto also noted that a Yankees scout was in attendance last weekend for the series against the White Sox.

These two teams are looking like legitimate trade partners, and with Cherington's history, that might not be a good sign.

Ben Cherington's trade history with the Yankees gives fans anxiety based on latest Pirates rumors.

The first trade Cherington made with New York sent Jameson Taillon to the Yankees in exchange for four prosepcts back in 2021. Roansy Contreras, Canaan Smith-Njigba, and Miguel Yajure each made it to Pittsburgh, but combined for a negative fWAR. Contreras is still pitching in Triple-A, while Smith-Njigba is a free agent and Yajure is overseas. The only remaining piece of this deal in Pittsburgh's system is Maikol Escotto, and he just got a promotion to Double-A after three seasons in High-A.

That trade was a complete disaster and looks terrible in hindsight. There is nothing good that came out of that deal, and it was one of the original trades that made Cherington look bad in his new role. He followed that poor trade with another one at the deadline that summer.

Eventual All-Star Clay Holmes was sent to New York in exchange for Diego Castillo and Hoy Park. Both have also combined for a negative fWAR and have not been in the organization since 2022. Park got the Pirates Inmer Lobo, an unranked prospect that has a career ERA of 1.67, in a separate trade. His presence hardly saves the deal, but at least that's something productive.

Those two were absolutely awful trades. Cherington and the Yankees did make one more minor deal that turned an injured JT Brubaker into Keiner Delgado, the Pirates' 26th ranked prospect per MLB Pipeline. It's too early to say anything about that one, really.

Now that there is a chance at another big trade with the Yankees, it serves as a major reminder that Cherington has not done well when he's matched wits with Brian Cashman. If avoding another fleecing means hanging on to Keller and others, so be it. Cherington may dig this organization into a deeper hole if this trend with New York continues, and thinking about these big trades completely frightens this fanbase for good reason.