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. Middleton is a two-way wing that can provide shooting simply by being an excellent spot-up threat, but he is also dangerous off movement. He can handle the ball as well, and score at multiple levels out of pick-and-roll or isolation. He has 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. Middleton is an excellent spot-up threat, but he is 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, 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. Defensively, Middleton is often tasked with defending the opponent's best wing, and is one of the better options to do so despite having a bigger offensive load than many guys playing that defensive role. He moves his feet well laterally, and has the size and length to contest shots. Middleton also still gets steals at a decenr ate. He's overall just a really smart defender, and has fit in well with a Bucks defense that has been one of the better defenses over the course of the last seven years. Middleton will likely continue to see some regression defensively as he ages, but I expect him to hold up well on that end for a little while longer at least. 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 haven't helped him in that regard.