It seems that almost every winter, Brian Cashman’s Yankees are active on the trade market. Last year, the team bought low on Jameson Taillon, who had missed most of 2019 and all of 2020. Two years prior, they reeled in James Paxton from Seattle and shipped out Sonny Gray. The 2017-2018 winter was highlighted by the blockbuster deal for Giancarlo Stanton, which saw the Yankees jettison Starlin Castro to Miami, although it also included smaller deals that sent Chase Headley back to San Diego and brought Brandon Drury to the Bronx from Arizona.
The safe bet says the same thing will be true this winter.