The Chicago Cubs and Chicago White Sox have made a few different trades over the last five years or so. Some have worked out for our Sox and some have not. It is fair to assume that each team would be cautious about making another one but it could be on the table.
The reason that it could happen is the state of each team. The White Sox are trying to revive their season in order to make it into the playoffs. It has been a tough start but you never know what happens in the second half.
The Cubs are one of the worst teams in the league and are only going to get worse when they sell off all their assets. They have a lot of players at the top of their roster that contenders might want for the playoff chase.
If the Chicago Cubs and Chicago White Sox came together for another trade, it might look something like this:
The Chicago White Sox could try and land an old friend in a deal with the Cubs.
The Chicago White Sox once had David Robertson on their team. He was their closer in a time when they were trying to win but failed to be a very good team. He has since bounced around but is now having a really good year with the Chicago Cubs.
The Cubs are likely going to maximize his value and get something for him while they can. If it is a low-risk type of trade, the White Sox would be smart to do with it. Micker Adolfo (13th ranked prospect in the organization) and Jason Bilous (16th in the organization) would be a solid package for both sides in a deal like this.
Adolfo would probably be able to finally get his chance in Major League Baseball which would be amazing to see. Robertson certainly wouldn’t be the closer on the White Sox but he would be a great arm to add to the bullpen. It is something to think about.