Bucks - get off an overpaid old wing who is always injured and never plays, replacing him with a young, 22yo 3&D wing on an amazing contract (locked at 18 for 5 years) who shoots 40% from 3 at 6'7, plus need PG depth and a solid 3&D wing versatile vet. Drastically improve their defense and starting unit. Also get JUST ENOUGH money off your books to get you below the 2nd apron. That allows you to aggregate contracts, which will allow you to pair young guys with Lopez/Connaughton/etc. to upgrade your roster without using additional picks. IMO, the only way the bucks can get significantly better is to move Middleton and his money off their books.

But maybe you hold out hope that Middleton comes back. When he does play, they're a high-end playoff team.

Bulls - This will certainly help the tank since Middleton is never going to play. You get draft capital.

The question for you is, is this enough? Pwill is young enough to be drafted in the 2025 draft and he's already locked in a good contract as the Bulls best defender who also shoots the three ball. Is it worth it to give him up for a first? After all, you're just going to have to use it gambling on finding his replacement. No particular reason to give him up now.

All considered, who says not? One? Both?