15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
New York Yankees v Toronto Blue Jays / Abelimages/GettyImages
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5. July 28, 2021: Yankees Trade 4 Prospects for Joey Gallo

Why isn't this one rated higher? All four of the prospects sent to Texas were going to be traded or nicked off the 40-man roster to clear room to protect more coveted Yankees. All due respect to Josh Smith and Ezequiel Durán, but neither has shown the type of potential exhibited by Peraza, Volpe or Cabrera. The Yankees were trading from a surplus, and they thought they were filling a need with every stathead's 40-homer-hitting obsession.

However, those in the know always knew Gallo might have trouble adjusting to New York. Brian Cashman didn't listen to those evaluators, supplementing his acquisition of Perfect Fit Anthony Rizzo with one of the worst possible partners.

"There may be deeper issues at play than simply letting Gallo rediscover his groove at the plate. Heyman cited a scout who said the Big Apple is a 'challenge' for the two-time All-Star and 'gets in his dome.'"

Bleacher Report

Gallo was almost impossibly bad with the Bombers, hitting 25 homers in 140 combined games across two years, but batting .160 in 2021. "He's not a high-average guy, but he's not that bad," every Yankee fan said prior to 2022 before watching him bat ... .159. The power didn't come as regularly, the whiffs piled up (a ghastly 194 in those 140 games), and every New York trend continued after the deadline in Los Angeles (57 more Ks in 117 at-bats, .162 average).

There will never be a more unpleasant player to watch in Yankees history. At the moment, Gallo's rivaled only by That One Ronald Guzman Game Where He Whiffed, Whiffed, Dribbled Into a Killer Double Play and Didn't Hustle to First.