Trade 1
Finding more pitching could be the key to the White Sox actually building some sustained success over the next decade or so. Their core is in place as far as the starting lineup but they still need some more starters and relievers to play well. Ken Giles might be a good acquisition for the White Sox in 2020 if they believe they are able to resign him. Trading for him so he can see what this place is like first might help him make up his mind.
Because his stay isn’t guaranteed, they wouldn’t trade one of their top prospects for him. If there was an elite player with lots of time left on his deal, the Nick Madrigal or Andrew Vaughn type prospects might be in play but they wouldn’t be here. A trade of two guys like Jonathan Stiever and Zack Collins for Giles would be a good move for the White Sox.
Stiever is still young at 22 so you never know how he is going to pan out. The White Sox have other young starters in the mix so if they gave him away it might not be that big of a deal. As for Collins, it is hard to see him having much playing time in 2020. Yasmani Grandal signed a four-year deal for a lot of money and James McCann is back for another year. If McCann is gone after this year, they still have Yermin Mercedes and Seby Zavala to back up Grandal. If this was a trade that the Jays would accept, you do it if you’re the White Sox.