Trade One
Kyle Hendricks is a one of a kind pitcher. He would come in and be a great addition to the White Sox rotation. Most Sox fans have probably watched him play because he is just on the other side of town. A good MLB comparable is Mark Buehrle. He isn’t going to blow 101 miles per hour past anyone but he is going to throw strikes that include a really good changeup. He is the type of guy that is worth giving up a bunch of prospects.
Jared Kelley, Jonathan Stiever, and Micker Adolfo are all top-ten Chicago White Sox prospects. This is a much better return for Hendricks than they got from the San Diego Padres for Yu Darvish a few weeks ago. That was more of a money dump than this would be so they are naturally going to get more of a return but this would be nice for the North Side.
In the case of Jared Kelley and Jonathan Stiever, the Cubs would be getting two pretty nice pitching prospects. Stiever has already made it up to the MLB and he would probably stay there on a less deep team than the White Sox. For Kelley, he fell to the White Sox in the second round of the 2020 MLB Draft in large part to the fact that the high school season was canceled. He has elite arm talent that could develop into a very good pitcher.
The Cubs don’t really develop pitching well but adding these two might help them turn that narrative around. Micker Adolfo is the White Sox number eight prospect as an outfielder. With the group that they have there already, it is hard to see them ever really finding a use for Adolfo outside of trading him for a missing piece. The Cubs have a long term need in their Major League outfield so adding as much potential help as possible would be smart.