4. Dallas Keuchel - 2020
Things did not go well for the Chicago White Sox and Dallas Keuchel.
Dallas Keuchel was not a good player for the Chicago White Sox outside of the one short 2020 season in which he was a Cy Young-caliber starter.
Things got so bad for him in 2022 that he ended up being cut. Following that, news of him being a back locker room guy got out there and he ended up with two other organizations.
It seemed like a great signing for one 60-game season but it turned around quickly. Looking back on the deal, it was a terrible decision by Rick Hahn and his staff. The day they cut him was celebrated hard by White Sox fans as the team couldn't win when he made starts.