The Chicago White Sox are not known to be a team that pays a lot of money for its roster. The entire roster might be worth a fair amount but they don't give single players what they are worth almost ever. It has caused them to be a mostly dissapointing Major League team.
The White Sox are one of just a handful of teams to never give out a 100 million-dollar contract. The highest-paid player in the history of the franchise is actually Andrew Benintendi who just signed this last off-season for 75 million dollars. He narrowly broke Yasmani Grandal's White Sox record.
Coming into every off-season, there are always roster needs. For example, this year it was second base and the outfield. Pitching is a need for all 30 teams every single off-season. However, the White Sox never spends top dollar on help which is sometimes needed to get teams over the edge.
If they would have handled free agency like a serious team during this rebuild, they would still be a World Series contender instead of the window only lasting for about two years. They could still be very good but it will get harder and harder without more help.
What happens when their own players worth over 100 million on this market come up to get paid? Are they going to just let them walk away because they are too cheap to retain them? These are the three players that might need that type of contract in the very near future: