One thing to note is that Middleton is kind of washed. He's no longer all-star Middleton and is often hurt. But this makes them deadlier offensively. But hurts their defense
I wonder if Middleton would be a full time PF nowadays if he was on another team without Giannis around. That injuries have sapped his quickness so much that he is now better at PF than at SF.
I also wonder if Middleton is now more comparable to someone like Tobias Harris as a player versus where he was two years ago as a legit All-Star who would be competing with the likes of Jaylen Brown. Possibly even better than Jaylen. Tobias Harris being a flawed 3rd option type with high skill level but needs to catered to in order to be consistently productive on offense, below average athleticism and below average defense. I see Middleton similarly.
I also wonder if Middleton can have a comeback year next season a year after serious injuries and improve some. That is what Bucks folks gotta be hoping for.
They should probably start trying to trade him for a quicker wing who can play some defense. A two way wing. Or trade for depth. Both could offer superior options for Milwaukee now given the lesser need for Middleton's offense with Lillard now on board.