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Photo by Alex Trautwig/MLB Photos via Getty Images As 2021 progresses, it is likely that the Yankees will start dealing. Cashing in trade chips could reinforce a roster chasing its first World Series title since 2009 after recent painful playoff eliminations. Upon reflection, it anecdotally occurred to me that the Yankees have done well recently at not trading away prospects who make them regret it. Luckily for New York, and for fan sanity, looking at recent deals confirms my earlier thesis. Cashman rarely trades prospects who then succeed elsewhere, regardless of whether the Yankees “win” each trade. But ye gods, the Yankees trade frequently. Accordingly, I limited my scope. I began with the acquisition of Didi Gregorius and ended with the James Paxton trade. Transactions since the latter need more time before we judge them.

New yorkUnited statesSan diegoJames paxtonGiancarlo stantonJorge mateoDavid robertsonZack brittonBlake rutherfordJorge guzmTyler clippardGiovanny gallegosErik swansonDustin fowlerLuke voitJustus sheffield