5. The Craig Kimbrel trade
One of the many star players shipped off during the 2021 fire sale was closer Craig Kimbrel, who was dealt to the White Sox in exchange for second baseman Nick Madrigal and relief pitcher Codi Heuer. It may be too early to call this deal a bad one for both parties because although Madrigal has struggled to find his place with the Cubs, Codi Heuer is on the verge of returning from Tommy John and could impact the bullpen soon. What is certain is that the White Sox definitely did not win this trade, as Kimbrel decided to absolutely forget how to pitch on the south side where he sported a 5.04 ERA in 24 appearances. As of the writing of this story though, this trade has just been a bust for all involved.