2. Andrew Benintendi
The White Sox didn't get what they needed from Andrew Benintendi.
Last off-season, the Chicago White Sox gave Andrew Benintendi the richest contract in the history of the Chicago White Sox. It was a great moment for him in his life but it was always risky.
The fact that he got the richest contract in team history makes it seem worse than it is. It is only worth 75 million which was market value for a player like him. The fact that they have never paid more for someone better is the true issue here.
It is unfortunate that the first of five years on this deal was a terrible one for him. He was truly terrible for the White Sox during the 2023 MLB season. His glove (which is supposed to be elite) was terrible out in left field and he couldn't hit either.
This is amongst the scariest contracts on the team. There is a tad bit more hope that he will bounce back than some of the other guys but you can't fully bank on it right now.
Benintendi has been a great player in his career. The White Sox were extra bad around him so we'll see how he responds in 2024. As of right now, the contract is very bad.