So, boredom has led me to post my 100/100, "all-in" scenario. I do not claim that these trades would be endorsed by the respective GMs, nor do I claim that I would make them if I were Hoyer. This is a WS-or-bust deadline recipe, just for fun and discussion.
Twins receive: Moises Ballesteros, Jaxon Wiggins, Kevin Alcantara, BJ Murray Jr.
Cubs receive: Joe Ryan, Willie Castro
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Marlins receive: Ben Brown, Christian Hernandez, Jonathan Long
Cubs receive: Edward Cabrera
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Orioles receive: Jefferson Rojas, Brandon Birdsell
Cubs receive: Felix Bautista
You can parse the details, but I would argue that the resulting team would be WS favorites.
The farm is utterly decimated, though we retain Owen Caissie to cover the potential departure of Kyle Tucker.