2 extensions the White Sox should make soon and 1 they should avoid
The Chicago White Sox are a very interesting organization. They have a lot of very talented players that need to find a way to put all of those skills to work. Most of them have underperformed based on the clear tools that they have.
It is a team that spends a lot of money on the roster as a whole but it isn't spent in the right areas. There are a few position players that make some good money but few of them actually deserve it right now.
Over time, the White Sox are one of a handful of teams to never hand out a 100 million dollar contract which is also something that should probably change soon. Andrew Benintendi has the most lucrative contract ever given to a White Sox player at 75 million.
Maybe a player on the Chicago White Sox will earn that type of contract as the years go on. They certainly don't seem like a team that will bring in someone worth that money from the outside but eventually, a few of their own players will want that kind of money.
The White Sox need to be really smart with their decision making.
You have to be very careful when handing out extensions though. You never want to sign anyone long-term that isn't going to perform for you and be worth it for the duration of the contract.
There are plenty of White Sox players deserving of a big extension and a few that are nowhere near worthy yet. These are two players the White Sox should work on extending right now and one that they should not:
The White Sox should extend these two players as soon as they can.
1. Tim Anderson
The Chicago White Sox should want to have Tim Anderson on their roster for as long as they can. He is a very good player that needs to be in this uniform for a very long time. Seeing him leave to go somewhere else would be just wrong.
He has embodied everything that it means to be a White Sox player over the years. It will take over 100 million dollars to do it but it would be worth it.
Anderson brings so much both on and off the field which is what this team needs. He is the face of the franchise and he drives the boat for them in every way. You pay guys like this when their time comes and his time is coming soon.
2. Dylan Cease
Dylan Cease is already starting to give Chicago White Sox fans nightmares when it comes to his long-term tenure with the club.
He signed Scott Boras to be his agent and then had a year in which he became the AL Cy Young runner-up. Both of those things help guys make lots of money in their careers. We could be talking 200 to 300 million if he keeps pitching the way that he has.
If there is a way to get an extension done as soon as possible, the White Sox should be all over it. They need him and they need him badly.
The Chicago White Sox should wait on an extension with this guy.
1. Lucas Giolito
The Chicago White Sox used to think that they were going to have to pay top dollar for Lucas Giolito. He had top ten Cy Young finishes in 2019 and 2020. He followed that up by coming in 11th in 2022 which still isn't bad at all.
In 2022, however, he was terrible. He wasn't "worst pitcher in baseball" level bad but he was no doubt, not himself.
There were some injuries, some issues with his newfound muscle, and just a lackluster team around him that caused some of these problems but it made it where the White Sox couldn't extend him right now.
Giolito could absolutely bounce back in 2023 and be worth a lot. That would make it clear that 2022 was just a fluke. Nobody should be surprised if that is actually the case in the end. However, you can't take that risk right now.
If that means that Giolito lets a different team overpay for him, so be it. The White Sox probably want to keep him badly to keep a nice starting rotation intact but if they can't, it won't be the worst thing.
Hopefully, by the end of the year, the attitude toward him as a player is changed and they want him long-term. That will mean that the team was better and will be better going forward.
Next. The 15 worst contracts in Chicago White Sox history. dark