Middleton developed into a consistent All-Star level player around the turn of the decade, and was a big part of helping the Bucks win their championship in 2021. In his prime, Middleton was a two-way wing that could provide shooting simply by being an excellent spot-up threat, but was also dangerous off movement. He could handle the ball as well, and score at multiple levels out of pick-and-roll or isolation. He had the size and length to guard multiple positions. The combination of all those factors made Middleton a top-30 NBA player during that time, and the Bucks may have won another championship in 2022 if he had not gotten hurt in the playoffs. However, he has suffered from injuries and age-related regression, and only played in 88 games over the past two regular seasons. He has struggled to make an impact in '24-'25, and the Bucks traded him for Kyle Kuzma in February. Middleton is an excellent spot-up threat, but he was asked to do a lot more than that though for the Bucks, as he was often the primary ball-handler in pick-and-roll before the Bucks acquired Damian Lillard in 2023. He knows how to get his defender in jail, and get floaters or short midrange jumpers off with a defender on his back. He isn't going to blow by defenders in isolation, and doesn't get to the rim very frequently, but he has a good enough handle to create separation, and his height and high release point allow him to get shots off over his defender, and he has been one of the best midrange shooters in the league over the past several years. Middleton experienced some shooting regression over the past two seasons. He has only hit 36.6% of his 3s over the past three seasons ('21-'24), after shooting 42% the two seasons before that. He shot really well from midrange in '23-'24, but overall he just hasn't had quite the same level of on-ball juice that he had in his late-20s. He shot well in '24-'25 when he did play, but on lower usage, and wasn't efficient in his limited minutes playing for the Wizards. He did help make them actually respectable during a stretch of games though. Defensively, Middleton was often tasked with defending the opponent's best wing, and was one of the better options to do so despite having a bigger offensive load than many guys playing that defensive role. He could move his feet well laterally, and has the size and length to contest shots. Middleton also still gets steals at a decent rate. He's overall just a really smart defender, and fit in well with a Bucks defense that has been one of the better defenses over the course of the last seven years. However, Middleton will likely continue to see some regression defensively as he ages, and the Bucks giving up on him in the way that they did is not a great sign for his ability to contribute at a high level going forward. Middleton will be nearly 34 years old as a potential free agent in 2025, so teams could be worried about the back-end years of a long-term contract for him, depending on the magnitude of that contract in terms of dollars, and his recent injuries and on-court struggles haven't helped him in that regard.