For the draft I am thinking if the Bucks can somehow steal Nikola Jovic, I think that would be the best option. Jovic will not be ready for another 2 or 3 years and really anyone that the Bucks take at their pick really won't be ready for awhile. If the Bucks decide to blow it up a little bit trading Middleton to Portland and then trading the 7th pick for more picks would be the ideal situation.
So something like this:
Trail Blazers get:
Middleton and Spurs 2023 1st round pick top 10 protected
Spurs get:
Josh Hart and #7 pick from the Trail Blazers and the Bucks 2023 second round pick
Bucks get:
9th and 20th pick from the Spurs and Anfernee Simmons from the Trail Blazers.
Then draft either Bennedict Mathurin or Shaedon Sharpe at the 9th pick or trade that pick for picks in 2023 and with the 20th pick hopefully he is available take Nikola Jovic and at the 24th pick take Patrick Baldwin Jr.
Kind of a crazy trade that will probably never happen.