The NBA trade rumor mill is heating up, and the Milwaukee Bucks are poised to make a bold move to reshape their roster around superstar Giannis Antetokounmpo. With the departure of Damian Lillard, the Bucks are left with a glaring void at the guard position, and a new target has emerged: Boston Celtics’ dynamic scoring guard Anfernee Simons. According to Jake Fischer of The Stein Line, the Celtics are open to trade discussions involving Simons, with talks expected to continue from now through the NBA trade deadline on February 5, 2026, at 3 PM ET. Could Simons, with his $27.7 million contract, be the key to revitalizing Milwaukee’s offense and restoring their championship contender status?
The Bucks’ decision to waive and stretch Lillard’s contract left them without their top perimeter scorer and primary playmaker. While signing Myles Turner bolstered their frontcourt, it did little to address the offensive firepower and shot creation lost with Lillard’s exit. Milwaukee’s subsequent moves—bringing back Kevin Porter Jr., Gary Trent Jr., and acquiring Cole Anthony—have added depth, but none of these players can replicate Lillard’s ability to dominate games as a scorer and facilitator.
Enter Anfernee Simons, a 26-year-old sharpshooter who has blossomed into one of the NBA’s premier volume shooters during his time with the Portland Trail Blazers. Simons is a walking highlight reel, capable of creating his own shot, splashing three-pointers at a high clip, and stretching defenses with his range. His ability to generate offense would pair beautifully with Giannis, giving the Bucks a dynamic backcourt weapon to complement their two-time MVP’s relentless interior dominance.
Simons’ fit in Milwaukee’s lineup is seamless. His quick-trigger shooting and ability to handle the ball would alleviate pressure from Antetokounmpo, allowing Giannis to operate more effectively as a playmaker and finisher. With Simons pulling defenders out to the perimeter, Milwaukee’s offense could regain the spacing and explosiveness it lost, making them a nightmare for opposing defenses.
Acquiring Simons won’t be easy. The Celtics, focused on trimming payroll this offseason, are reportedly exploring ways to move Simons’ $27.7 million salary. One potential deal could involve flipping Simons to the Washington Wizards for Kyle Kuzma, whose contract is more cost-effective in the short term. However, Boston is wary of taking on Kuzma’s longer-term financial commitment, which could complicate such a deal.
For the Bucks, constructing a trade package for Simons presents its own hurdles. Matching his $27.7 million salary will likely require including a significant asset like Bobby Portis Jr., a fan favorite and key contributor off the bench. Milwaukee might hesitate to part with Portis, whose versatility and scoring punch have been vital to their success. However, if the Bucks grow desperate for elite perimeter scoring, they may have no choice but to consider moving him.
Alternative trade packages could involve a combination of players like Gary Trent Jr., Cole Anthony, or even draft capital to sweeten the deal. The bigger question is whether Boston would be interested in what Milwaukee has to offer. The Celtics, fresh off a championship run, are in a peculiar spot—balancing financial flexibility with maintaining a competitive roster. A trade for Simons would need to align with their long-term goals, which could make negotiations tricky.
Despite the complexities, Anfernee Simons should be at the top of Milwaukee’s trade radar. His youth, scoring prowess, and ability to create offense align perfectly with the Bucks’ need to rebuild a contender around Giannis. A backcourt featuring Simons could unlock new dimensions in Milwaukee’s offense, providing the spark they’ve lacked since Lillard’s departure.
As the February 5, 2026, trade deadline approaches, the Bucks have a golden opportunity to make a splash and reassert themselves as Eastern Conference heavyweights. Landing Simons could send shockwaves through the NBA, signaling Milwaukee’s intent to reclaim their spot among the league’s elite. For now, all eyes are on the Bucks’ front office as they navigate the high-stakes pursuit of Boston’s $27.7 million scoring machine.