The Milwaukee Bucks find themselves once again at the center of NBA speculation as the front office signals that they may not be done reshaping the roster. After acquiring Myles Turner in what was already viewed as one of the most aggressive moves of the offseason, the Bucks are now being linked to Anfernee Simons of the Portland Trail Blazers. The news has sparked conversation throughout the league, not only because of the talent involved but also because it represents a bold recalibration of Milwaukee’s strategy in the post-Giannis championship window. The Bucks have consistently been a contender in the Eastern Conference since winning the 2021 NBA title, but in the years that followed, questions about their supporting cast, aging veterans, and roster depth have left them just short of reclaiming the throne. With Turner already in the mix to shore up the frontcourt alongside Giannis Antetokounmpo and Brook Lopez, the pursuit of Simons signals Milwaukee’s intent to build a more dynamic backcourt that can complement Damian Lillard while offering long-term security.
At first glance, the acquisition of Myles Turner was already seen as a coup. Turner’s reputation as one of the league’s premier rim protectors and floor-spacing big men made him a natural fit for Milwaukee’s defensive identity and half-court offense. His ability to stretch the floor with three-point shooting while also providing elite shot-blocking allows the Bucks to maintain a strong interior presence while opening lanes for Giannis and Lillard to operate. Turner also alleviates some of the defensive wear-and-tear that Lopez has carried in recent years, giving the Bucks a versatile big man rotation that few teams can match. For a team whose defensive backbone had begun to fray over the last two seasons, Turner represents stability and upside in one package. Yet, as valuable as he is, the move was not solely about Turner—it was about setting the stage for what could come next. That “next” piece may very well be Anfernee Simons.
Simons, at just 25 years old, has already established himself as one of the NBA’s most potent scoring guards. Known for his explosive first step, smooth shooting stroke, and ability to create off the dribble, Simons has emerged as both a deadly isolation player and a reliable perimeter threat. In Portland, his role expanded dramatically after Damian Lillard’s departure, giving him the chance to showcase his offensive arsenal. However, with the Trail Blazers now squarely in a rebuilding phase centered around Scoot Henderson and Shaedon Sharpe, Simons has become a logical trade chip for Portland’s front office. For Milwaukee, his availability represents an opportunity to pair two dynamic offensive guards—Simons and Lillard—in a system that thrives on spacing, drive-and-kick action, and pick-and-roll variations.
The potential acquisition of Simons raises fascinating questions about fit, roles, and the Bucks’ long-term outlook. On paper, Milwaukee already has one of the most dangerous offensive duos in the league with Giannis and Lillard. Adding Simons to the mix would give them another reliable perimeter scorer who can handle the ball, run secondary pick-and-rolls, and lighten the load on Lillard during stretches of the game. One of the glaring issues for Milwaukee in the postseason has been their reliance on Giannis and Lillard to carry the offense while role players struggled to consistently produce. Khris Middleton, once their steady All-Star-level closer, has battled injuries and declining athleticism, making it difficult for him to replicate his 2021 Finals brilliance. Simons, in many ways, could be seen as the successor to Middleton—a player who can hit contested shots, space the floor, and create his own looks late in games. If the Bucks’ front office indeed views Simons as part of their future core, this move could represent a changing of the guard within the franchise.
Of course, there are complications to any deal of this magnitude. The financial implications alone are significant. Simons is under contract on a four-year, $100 million deal signed in 2022, which means Milwaukee would need to navigate salary-matching mechanics while also considering the luxury tax. After trading for Lillard, the Bucks are already deep into the financial commitments of a contending roster, and adding another sizeable contract would put them among the league’s most expensive teams. However, ownership has indicated a willingness to spend as long as the team remains in contention, and given Giannis’ continued dominance, the championship window remains open. Moreover, Milwaukee may view Simons’ age and trajectory as worth the investment, especially if they see him as both an immediate contributor and a long-term cornerstone.
From a basketball perspective, there is no question that adding Simons would elevate Milwaukee’s offensive ceiling. He is a career 38% three-point shooter who can thrive both on and off the ball, a vital skill set when sharing the court with Lillard and Giannis. In lineups where Giannis dominates the paint and Turner stretches the defense vertically, Simons’ shooting would provide even more space for Lillard to operate. The offensive schemes could become devastatingly versatile, with endless combinations of high pick-and-rolls, drive-and-kick actions, and floor spacing that few defenses could consistently contain. Milwaukee has long relied on defensive dominance to mask offensive stagnation, but this would flip the script—turning them into one of the most feared scoring machines in the NBA.
Yet, there are valid concerns about the defensive end. While Turner’s rim protection can cover for certain perimeter lapses, pairing Lillard and Simons in the backcourt would create defensive vulnerabilities. Both players are undersized guards who have struggled to consistently defend at a high level. This would put tremendous pressure on Giannis, Turner, and Lopez to clean up mistakes, rotate effectively, and protect the rim. It’s possible that the Bucks could get away with this in the regular season by overwhelming opponents offensively, but in the playoffs, where every possession is magnified and mismatches are hunted relentlessly, it could become a liability. The front office would need to consider whether the offensive firepower Simons brings outweighs the potential defensive drawbacks, and whether head coach Doc Rivers could construct a scheme to minimize those issues.
Another factor to weigh is team chemistry. Lillard is already the unquestioned leader of the backcourt, and Giannis remains the franchise cornerstone. Integrating a young, high-usage guard like Simons into an established hierarchy requires careful balancing. Would Simons be comfortable adjusting to a role where his touches decrease and his responsibilities shift more toward secondary playmaking? Could he develop the patience and discipline to thrive as a complementary piece rather than a primary scorer? These are the questions that Milwaukee’s front office and coaching staff must consider before making such a move. However, Simons’ skill set does suggest that he could adapt. He has played both as a lead ball handler and as a catch-and-shoot option in Portland, demonstrating versatility that could translate well alongside Lillard and Giannis.
In the broader context of the Eastern Conference, this pursuit makes strategic sense. The Boston Celtics, fresh off a dominant championship campaign, are loaded with wing talent and versatile defenders. The Philadelphia 76ers are retooling around Joel Embiid and Tyrese Maxey. The Miami Heat remain a playoff-tested squad with Jimmy Butler and Bam Adebayo. If the Bucks want to keep pace with these rivals, they must continue to evolve. Standing still in the NBA is often the same as falling behind. By targeting Simons, Milwaukee is signaling that they are not content with merely being competitive—they want to be overwhelming. They want to stack enough offensive talent that no defensive scheme can fully neutralize them.
It’s also worth noting the ripple effects such a move would have on the rest of the roster. If Simons were to arrive, it likely means changes for players like Malik Beasley, Pat Connaughton, or even Middleton. Depth would need to be reshaped to balance the rotation, and there may be sacrifices in terms of defensive specialists or veteran glue guys. However, the Bucks’ front office has shown a willingness to make bold, even ruthless decisions in pursuit of championships. Trading for Lillard last season was proof of that, and now, chasing Simons suggests a continuation of that all-in mentality.
Ultimately, the pursuit of Anfernee Simons reflects a franchise at a crossroads but unwilling to compromise. The Bucks know that Giannis is in his prime and that windows for contention do not stay open forever. They also understand that the league is shifting toward younger, faster, more dynamic offensive cores. By pairing Turner’s defensive anchor with the offensive dynamism of Lillard, Giannis, and potentially Simons, the Bucks would be creating a roster designed to score with anyone while still maintaining enough defensive presence to compete at the highest level. It is a high-risk, high-reward strategy, but for a team chasing another championship before their stars age out of dominance, it may be the kind of bold gamble that history rewards.
If Milwaukee ultimately pulls the trigger on such a move, it would reshape not only their own outlook but also the balance of power in the East. Rival teams would be forced to account for a Bucks squad that could beat opponents in multiple ways, and playoff matchups would become even more unpredictable. Whether or not the deal materializes, the fact that the Bucks are targeting someone like Simons shows that they are serious about reinventing themselves. They are not a franchise content to rest on past success or incremental improvements—they are going for it. And in today’s NBA, where dynasties are fleeting and opportunities must be seized, that mindset might be exactly what keeps them in the championship conversation.
