Trade throw-in could fill Bucks Khris Middleton-sized wing hole

The Milwaukee Bucks have featured a variety of talented guards and dynamic big men to compliment Giannis Antetokounmpo constantly since Giannis emerged as an All-NBA level player. From Jrue Holiday to Damian Lillard, and Brook Lopez to Myles Turner, the Bucks have found skilled guards and bigs consistently.

Even this season as Milwaukee has struggled post-waiving Lillard, Kevin Porter Jr. and Ryan Rollins have at times looked like capable replacements as a guard duo. What the Bucks have missed though, for nearly four years now, is dynamic two-way wing play.

Khris Middleton’s MCL sprain in the 2022 NBA Playoffs was the beginning of the end for Milwaukee’s wing depth. Middleton managed to gut out good playoff outings in 2023 and 2024, but not without further injuries slowing him down and ultimately leading to the Bucks attaching draft capital to flip him for the younger and cheaper Kyle Kuzma in 2025.

Kuzma has had some nice games in Milwaukee and has embraced a limited role offensively to help the team, but lacks the consistency and shooting acumen to truly fill in for Middleton. A career 33.4% three-point shooter, Kuzma is sitting below that average at 32.2% this season. Not exactly the spacer on the wing Milwaukee had with Middleton, the franchise’s all-time leader in threes made.

The Bucks did add Taurean Prince via free agency to provide that spacing from the small forward spot, and he’s been a sensational 43.8% shooter as a Buck. Prince lacks the playmaking of Middleton though, and unfortunately has missed all but eight games this season due to a neck injury.

The hole at small forward has plagued the Bucks all season long. They’ve tried small lineups with A.J. Green there, but Green’s more fit to play shooting guard and has struggled against some larger forwards. Given the premium value placed on two-way wing players around the NBA, this seemed like a huge issue both this season and going forward for the Bucks. Would it take all of their draft capital to find a capable small forward? Would two future picks and one in the 2025 NBA Draft even be enough?

Perhaps it only took Cole Anthony and Amir Coffey. The Bucks dealt that duo on NBA Trade deadline day for Nick Richards and Nigel Hayes-Davis, before waiving Hayes-Davis and rerouting Richards to Chicago in exchange for Ousmane Dieng.

Dieng, who had already been traded from Oklahoma City to Charlotte and then from the Hornets to the Bulls, seemed like a worthy yet far-fetched flier. After all, if probably the smartest front office in the league was willing to pair a 2029 second-round pick to dump him and two more teams made the same decision, could there be real upside in Ousmane Dieng?

Apparently the answer is absolutely. Dieng caught fire with his jumper against the Orlando Magic in his first extended run for Milwaukee, hitting five of eight threes and shooting 6/10 overall while also adding three rebounds.

That good first impression led Milwaukee’s coaching staff to start Dieng the next night in Oklahoma City. Both teams were down key players, with Giannis Antetokounmpo, Myles Turner, Ryan Rollins, Shai GIlgeous-Alexander, Jalen Williams, and Isaiah Hartenstein all sitting out. The Thunder’s renowned depth had them as double-digit favorites heading in. But it was the depth player they paid to salary dump who swung the game.

Players under 23 to put up 15/10/5 with 4+ blocks in a game this season:

- Victor Wembanyama
- Ousmane Dieng

WOW. pic.twitter.com/CmWrAJtXk9
— Bucks Lead (@BucksLead) February 13, 2026

Dieng was sensational, building on the strong shooting from the night before but impacting the game on both ends of the floor. He posted 19 points, 11 rebounds, 6 assists, 1 steal, and 4 blocks while shooting 7/12 from the field and 3/6 from deep. Milwaukee rolled, blowing out OKC 110-93.

Dieng’s number of highlights in those 36 minutes is more than just a revenge game heater – he was legitimately disruptive defensively and on the boards, and showed his handle and touch offensively throughout the game.

Ousmane Dieng is only 22 years old.

19 PTS | 11 REB | 6 AST | 4 BLK | 58% FG pic.twitter.com/jGAbeoxjoS
— Milwaukee Bucks (@Bucks) February 13, 2026

If Dieng can maintain anywhere near this level of play, it will be a huge deal for Milwaukee. The Bucks have been searching in vain for an impactful two-way wing who fits with Giannis for most of this decade, and seemed far from finding one. Now they’ve got a 22-year-old who has hit the ground running, and Milwaukee has pole position to keep Dieng via restricted free agency this summer.

It would be fitting for that much-needed wing to arrive as a completely unheralded afterthought. While he became a Bucks legend eventually, Middleton himself was just added salary to facilitate the Brandon Jennings for Brandon Knight swap with Detroit.

Milwaukee could sure use another diamond in the rough to shine as the Bucks look to re-tool around Giannis on the fly. Ousmane Dieng has a golden opportunity down the stretch to prove he’s the answer to the Bucks wing issues.