We all know that the Chicago White Sox really took advantage of the Chicago Cubs in 2016 when they acquired Eloy Jimenez, Dylan Cease, and two other prospects in exchange for Jose Quintana. The Cubs overpaid for Quintana because he was a cost-controlled pitcher that was okay at the time. He was a disaster for them, Cease has nasty stuff in the White Sox current rotation, and Jimenez is a superstar offensive player now.
With that said, the Cubs might not want to make another deal with the White Sox. However, they would be doing their organization a disservice by not trading with the White Sox for any of those reasons. In fact, the White Sox might be willing to pay more due to the fact that they believe they can win the World Series right now.
Of course, the Cubs have a lot of players on the market right now. Craig Kimbrel would fit in any bullpen but would make a great setup man for the White Sox. Javier Baez would be able to play some solid second base. Anthony Rizzo is really the only one that doesn’t have much of a fit there. Kris Bryant might fit on the south side more than anyone because of the fact that he could play any position.
Kris Bryant would fit in on the Chicago White Sox in so many different ways.
On Tuesday night, the Cubs took him out of the game in the middle of it which started a whole bunch of conversations. They later announced that it was because of an injury and not because he was traded but that could be true or false. He is clearly someone that is on the block right now as his contract is up at the end of the season. If the White Sox acquired him before the deadline, it might look something like this: