Cardinals receive: RHP Dylan Cease
White Sox receive: SS Masyn Winn, OF Dylan Carlson, LHP Matthew Liberatore
If I had to rank the five trade packages based on what I would do, this would be the third-best trade in my opinion. I would much rather offer up one of the first two deals than throw Masyn Winn into the conversation, but if he is who the White Sox covet, I think it's still worth having a conversation.
I'm a huge fan of Winn. He's already showing flashes of his defensive upside and speed on the basepaths. His bat was shaky in his brief stint in St. Louis, but even Winn has been quick to acknowledge that he typically takes some time to get used to each level at the plate. If he can continue to develop as a hitter, he's an extremely valuable shortstop for years to come.
Here is the question I would be asking myself if I were the Cardinals: What are the chances that Masyn Winn will be a top-5 shortstop in all of baseball long-term? Or even a top-10 player at the position? It's been a long time since the club has had a long-term solution at shortstop, and if they truly have a top-end shortstop on their hands, I have a lot of pause here. But if they are just hoping he becomes that but are unsure of that ceiling, then he's not untouchable when it comes to getting a guy like Cease.
Again, I'm not quick to move him, and I'd much rather give up a strong package of prospects or something involving Edman instead, but if the White Sox after one of the Cardinals' young middle infielders, I think Winn is the one I would part with first. Nolan Gorman and Brendan Donovan mean way too much to this club's offense, and Edman is more than adequate to cover shortstop if needed.
Accompanying Winn in this deal are two guys the White Sox can bank on regaining their value in Dylan Carlson and Matthew Liberatore. Carlson is a former top-20 prospect in all of baseball and still has the potential to be a meaningful outfielder in this league. His bat against right-handed pitching needs work, but he destroys left-handed pitching and is a good defensive outfielder. Liberatore is a former top-100 prospect who has struggled to establish himself as a rotation option in his young career. He would be an interesting third piece for the White Sox to consider here.
Hopefully I've been clear, but if I haven't, let me say it again. I don't want to trade Winn and would name a lot of other players I would part with before him. But it's not a trade I'm a hard no on.