The Bucks would almost have to include Jrue Holiday to make this kind of a deal. Middleton is not going to sign only to get traded to Washington. Same with Brook. If not Jrue, would have to move the majority of the roster (Portis, Connaughton, Allen, etc). Really no 1st-round picks to work with.

Jrue Holiday:

23-24: $36.8M
24-25: $39.4M (PO)