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.