3 of the worst Chicago White Sox MLB Trade Deadline deals in the last 15 years
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.
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.
3. Cesar Hernandez for Konnor Pilkington (2021)
The Chicago White Sox really didn't do well at the 2021 trade deadline.
The trade for Cesar Hernandez isn't one of the worst White Sox trades in the last 15 years because of the fact that Konnor Pilkington is this amazing player.
It is because of what Cesar Hernandez wasn't for the White Sox. At the time of the trade, he was probably the second-best hitter on the Cleveland squad only behind Jose Ramirez.
He had 18 home runs at the time of the deal. He went on to only add three more for the rest of the season. It was a very bad stretch for him.
In fact, when that season with the White Sox ended (lost to Houston Astros in four ALDS games), he went to the Washington Nationals in 2022 and was horrible. Going to the White Sox was detrimental for him in a lot of ways.
This is also a player that had a Gold Glove at second base under his belt. It came from his older days with the Philadelphia Phillies but he was still a really good defensive player up to that point. It all fell apart with the Sox.
They ended up thinking that Leury Garcia was a better option at second base in the playoffs and they were right which is sad to say.
If you are wondering why all of these trades are in recent memory, it is because of the fact that the White Sox aren't .500 or better trying to win very often. When they are good though, they are bad at making trade deadline trades.
Next. The 15 worst contracts in Chicago White Sox history. dark