The Chicago White Sox are normally a very bad baseball team. They don't make the playoffs very often which is something that makes a lot of fans very upset.
They have made it a handful of times in recent memory but not nearly enough for being in a division like the AL Central.
A fact like this also means that they don't buy very often at the MLB Trade Deadline. They have only been a team that acquires players to try and win a handful of times.
Most of the time, they are that team trying to sell. When they have been buyers, however, they haven't always been smart.
These are the three worst deals that they have made at the deadline in the last 15 years:
1. Craig Kimbrel for Nick Madrigal and Codi Heuer (2021)
The Chicago White Sox made a bad trade with the Chicago Cubs in 2021.
The Chicago White Sox felt like they needed another closer in 2021 despite having Liam Hendriks who was the best in the league at that point.
They also didn't even end up using Kimbrel as a closer either which made it even more maddening. He is a closer through and through but Tony La Russa insisted on using him as a setup man.
Of course, Codi Heuer has been almost exclusively hurt as a member of the Chicago Cubs. He has some tremendous talent but we are still waiting to see him back.
As for Nick Madrigal, he was a really nice contact hitter for the White Sox before his injury. Then, when he came back with the Cubs, he struggled.
You never know how things would be different for him if he were never traded. One thing that is for sure is the fact that he'd be a better option than what the White Sox trot out there now in 2023.
Although it didn't work out amazing for the Cubs either, it is a really bad trade for the White Sox because it messed a lot of things up.