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USA Today
Overview
Considered to be one of the most sought-after wings on this summer's market (behind only Kevin Durant and Kawhi Leonard), Middleton's first foray into the free agency may be a short one; the Texas A&M product declined his $13 million option this past week, but is reportedly working closely with the Milwaukee Bucks to reach a new long-term deal that would keep him in green and cream for the duration of his prime years. Middleton is an ideal No. 2 or 3 offensive option on a contender, which is exactly the kind of role he has carved out in Milwaukee (serving as the principal secondary scorer behind Giannis Antetokounmpo). After earning his first ever All-Star appearance this past season, Middleton will undoubtedly look to continue racking up personal accolades while putting his team in position to contend for an NBA title.
Regular Season Per Game Stats: 18.3 points, 6.0 rebounds, 4.3 assists, 1.0 steals and 0.1 blocks on shooting splits of 44/38/84 (FG%/3PT%/FT%).
Postseason Stats: 16.9 points, 6.3 rebounds, 4.4 assists, 0.6 steals and 0.0 blocks on shooting splits of 42/44/89 (FG%/3PT%/FT%).
Age: 27
Strengths
Middleton is a prototypical wing in today's NBA; he's able to operate within the pick-and-roll/pop with aplomb, splashing jumpers from out to 30 feet or showcasing his handles en route to a finish around the rim. Offensively, there are no nits to pick with his game - he's the proud owner of a sterling career shooting line (slashing 45/39/87) and still has years to continue expanding his arsenal of skill moves and dribble drives. His immense physical tools (6'8" height, 222 lbs, 6'9" wingspan) allude to the possibility of Middleton becoming an elite defender, and his height and shooting form gives his jump-shot a nearly unguardable release point.
Weaknesses
While Middleton has the physical tools to become an elite defender, he is not one currently, as his individual defensive box score numbers indicate. He has the foot speed and reach to successfully transform into a downright scary perimeter stopper, capable of covering the opposing teams primary or secondary option every trip down the floor. But, despite his sizeable role in a league-leading Bucks defense last season, Middleton has work to do for himself on that end of the floor.
Ideal Role
Middleton is the ideal starting small forward for a championship contender. Provided he isn't the No. 1 offensive option, he can score efficiently on significant volume; you can count on him for 20 points per game on 45%+ FG shooting. He should be earmarked to play anywhere from 32-38 minutes per game, and would thrive on the court with (at least) two other adept shooters. He spaces the floor, and can handle the ball very well for a backcourt-frontcourt tweener. Ideally, he would play alongside an elite defensive guard and a rim-patrolling, shot-swatting centre.
Possible Landing Spots
Milwaukee Bucks: The most likely location for Middleton to land in would be Milwaukee. The Bucks have assembled a contender, and are well-positioned to make significant noise in the East for years to come. He would be able to continue playing alongside a similarly-aged superstar and likely MVP in Giannis Antetokounmpo, a luxury very few other teams can offer. Running it back in Milwaukee would represent the safe and logical choice for Middleton this summer.
Los Angeles Lakers: The Lakers would pitch Middleton on being the final piece of the puzzle for a 17th championship title squad in Los Angeles. The opportunity to play with LeBron James and Anthony Davis could be too good to pass up, as would the LA weather, and the fame that would come with being a part of the most recent team to bring a Larry O'Brien trophy to the purple and gold faithful. Middleton's long-range shooting and prototypical wing attributes would represent the exact kind of player the Lakers are looking for to surround Davis and James. While the Los Angeles front office might consider Middleton to be a B-tier free agent, they should have no qualms about signing him to a max contract to fill out their star-studded core.
Dallas Mavericks: The Mavericks would absolutely love to form a star-studded triumvirate of Doncic, Porzingis, and Middleton; that trio would offer elite shooting, immense physicality on the defensive end, and plenty of time to grow together (Middleton turns 28 in August, while Porzingis would be 24 and Doncic would enter the season still only 20 years old). Dallas would offer Middleton perhaps the best chance at contending year-over-year in the Wild West without hitching his wagon to an aging LeBron and largely dysfunctional franchise in the Lakers.
Expected Next Contract: 5 year/$190 million max contract from the Bucks, or a 4 year/$141 million max contract elsewhere. There is no chance Middleton signs anything less than a max contract this offseason given his superlative skillset, experience, and relatively clean injury history. You can likely count on that contract being with the Bucks; they are the team that realized his ascent to stardom while building a contending roster, and have every incentive to keep Middleton around for the extent of his (and Giannis') prime.