Major League Baseball history is filled with trades that haunt teams for years, and several deals from the past six years stand out as particularly regrettable. Notable trades between January 1, 2017, and December 31, 2023, resulted in teams losing players who could still be under their control in 2025. Not included are trades that involved players who had already become free agents or were on the verge of free agency.

The Chicago Cubs’ decision to send Dylan Cease and Eloy Jiménez to the Chicago White Sox for Jose Quintana exemplifies a painful trade. While Quintana was expected to be a top pitcher, he failed to deliver, while Cease has developed into a Cy Young contender.

Another disastrous trade involved the St. Louis Cardinals dealing Sandy Alcántara and Zac Gallen to the Miami Marlins for Marcell Ozuna. Alcántara has become an elite pitcher, making this trade particularly stinging for the Cardinals, especially in light of their recent struggles.