The Chicago Cubs could certainly use some pitching and the White Sox have that.
The Chicago White Sox has a loaded system when it comes to pitching. At the MLB level, their rotation consists of Lucas Giolito, Lance Lynn, Dallas Keuchel, Dylan Cease, and Carlos Rodon. They also have both Michael Kopech and Garrett Crochet who are future starters as well. If they stay healthy, it could be a loaded group for a long time. With players like Aaron Bummer, Codi Heuer, and Liam Hendriks in the bullpen, they are pretty set there too for a while.
Part of the reason is that they are deep organizationally. They draft and develop pitching well. The Cubs, on the other hand, don’t do that at all. In fact, they have done a terrible job at it during the Theo Epstein/Jed Hoyer era. They are trying to fix it now before it is too late and they have to completely start over.
One way to do it is to make sure they get some good young arms when they make their trades. We all know some big names are being traded so they might as well try and add arms. Jonathan Stiever, Jimmy Lambert, and Tyler Johnson are all pitchers in the White Sox organization that could move to the North Side and work on their development. If this trade went down, it is fair to assume that both sides would be happy.