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: