Chicago Cubs: 3 trade packages with the Chicago White Sox

The Chicago Cubs and Chicago White Sox both have a long history of being interleague rivals. They mean absolutely nothing to each other in terms of standings or playoff seeding but being two teams in the third largest American metropolitan will create a natural rivalry. However, each team would be smart to not let a fan rivalry get in the way of business either. They need to be careful with it in a respectful way but it shouldn’t ever keep them from doing business.

The Chicago Cubs and Chicago White Sox would be wise to make a big trade.

Each team is trending in the opposite direction. The Cubs have had lots of recent success but it is all coming down. The peak was winning the World Series in 2016 surrounded by a few other deep playoff runs. Now, in 2021, they aren’t very good. They had some people fooled early in the year but this team is going nowhere. With all of the expiring contracts for star players that they have, they can get a haul on the trade market.

As for the White Sox, they have been the opposite. They began to rebuild thier organization the right way in 2016 much like the Cubs did in 2012. Their window is now wide open to try and win as much as possible over the next 8 or so years. They have a long way to go but they are legit World Series contenders if they start to get just a bit healthier.

The White Sox have prospects to give up for rental players if the Cubs were willing to do something like that. We don’t know how active each team is going to be in either direction yet. If they were to make a trade with one another, it might look like one of these: