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.