2. Jake Diekman for Reese McGuire (2022)
The Chicago White Sox should have never acquired Jake Diekman.
The Chicago White Sox were struggling for most of the 2022 season but it was nothing like what they are going through right now.
They should have considered adding something good at the deadline to help kick-start a hot stretch. They could have easily won the very weak AL Central but they chose to let the trade deadline come and go.
In fact, the only move they made at all at this 2022 deadline was the move to acquire Jake Diekman. He was horrible for the White Sox for the rest of the season, including blowing the biggest game of the season against the Cleveland Guardians with the division in reach.
Reese McGuire wasn't all that good for the White Sox in his short tenure there either but he turned it around with the Boston Red Sox which is where Jake Diekman came from.
The White Sox ended up DFAing Jake Diekman here in 2023 and he has since gone to the Tampa Bay Rays to start playing well. It is a shame. This trade will always be remembered as a disaster.