Well, he is entering his prime, and Milwaukee at during his first two playoff runs was a garbage team anyway barely making the playoffs. i wont hold anything against him while being coached by Jason Kidd tbh
2 years ago like you said his playoff numbers were pretty damn good. Last year, yeah he struggled against the suffocating defense of Toronto but so did Giannis. He was just fine in the previous two rounds. But yeah he really did struggle against Toronto, so i get it, but i don't think its fair to hang that over him. all teams/players have to go through their growing pains of failures before getting to the top of the mountain (except Timmy tbh) and I believe they have paid their dues and this is the year they'll break thru.
but like i said, he has taken a significant step forward (imo) this year along with Giannis and there is no team anywhere close to them in the East, there is no Kawhi or LBJ for them to run into, and having a player like Giannis to play off of who is having a GOAT level season is going to make it easier for him. i'm not saying Middleton is a #2 like Davis or PG, but i do believe within the scheme the Bucks play and having a #1 like Giannis, he is going to be fine. plus he plays both sides of the court. the Bucks interior D is suffocating, the only way they are going to get beat is if a team gets super hot from deep over a 7 game series which i dont see happening.