The Milwaukee Bucks are sort of like how the Cleveland Cavaliers were following the 2017 season where they lost their 2nd best player [Jrue Holiday/Kyrie Irving], have an aging and thin supporting cast next to their star and limited assets. A player they could have used and given up very little for is Bradley Beal, but that ship seems to have sailed.
-Giannis
-Bropez
-Bobby Portis
-2024 late first
-2024 early second
-2026 worst of Pelicans/Bucks first
-2028 worst of Blazers/Bucks first
-2030 worst of Blazers/Bucks first
-2031 second
The first thing I would look to do is add youthful depth. Dennis Smith Jr, Lonnie Walker IV, Cam Reddish and Naji Marshall are all cheap free agent options who could upgrade their 8th/9th man slot(s) and in their mid-20's.
Given the asset, they should try to add another ball-handler as Giannis is a ~75 game player while Lillard is a ~70 game player but aging. I would reach out to the Lakers and see if they would swap Gabe Vincent with Pat Connaughton. If that isn't available, one of Jordan McLaughlin or Monte Morris could be the odd man out in Minnesota, and see if you can get one of them for < tMLE [Morris being worth more than McLaughlin, though McLaughlin being younger].
Aiming higher, I would also reach out to Charlotte to see what they would require to move Grant Williams, Utah for Jordan Clarkson and Sacramento for Kevin Huerter.
The highest-end move I could see is something like Brook Lopez for Wendell Carter Jr. Milwaukee generates a TPE and lock's in a cheap Center for the next 2 seasons while Orlando add's a floor spacing Big next to Paolo at the 4 whom is an elite rim protector and keeps flexibility moving forward in terms of cap space.
The biggest thing here are the following:
1) Middleton is still a good player and just needs to be healthy.
2) Keep the picks for one more season, being patient if an actual high-impact player comes available
Here is an example of a potential roster for 2024-2025
Damian Lillard/Tyler Kolek [Rookie]/Jordan McLaughlin
Malik Beasley/Marjon Beauchamp/Lonnie Walker IV
Khris Middleton/Pat Connaughton/Cam Reddish
Giannis Antentokounmpo/Bobby Portis
Brook Lopez/Mo Bamba or Mason Plumlee