The Milwaukee Bucks, once towering giants of the NBA with their 2021 championship triumph, have stumbled in recent years, plagued by three consecutive first-round playoff exits. The shine of their glory days has dimmed, and the team finds itself at a crossroads. However, hope is stirring in Milwaukee. The Bucks have made waves in the offseason by signing free agent center Myles Turner, pairing him with superstar Giannis Antetokounmpo to form a formidable defensive frontcourt. Rumors are now swirling that Milwaukee is eyeing a blockbuster trade for Boston Celtics guard Anfernee Simons to bolster their backcourt scoring, especially after the departure of Damian Lillard. With these bold moves, are the Bucks poised to reclaim their place among the NBA’s elite for the 2025-26 season, or is this a risky gamble? Let’s dive into the details and explore what this could mean for Milwaukee’s future.
Giannis Antetokounmpo
The Bucks’ recent struggles are undeniable. After their 2021 championship, powered by Giannis Antetokounmpo’s transcendent play, Milwaukee has faltered, posting a 48-34 record last season—their worst winning percentage since 2017-18, when they won 44 games and fell to the Boston Celtics in the first round of the playoffs. The departure of Damian Lillard, a nine-time All-Star who suffered a torn Achilles in the 2025 playoffs, left a gaping hole in the Bucks’ backcourt. Lillard’s scoring (24.9 points per game) and playmaking (7.1 assists per game) were critical, and his absence has forced Milwaukee to rethink their roster construction around their two-time MVP, Giannis Antetokounmpo.
Enter Myles Turner, a game-changing addition in free agency. Signed to a four-year, $107 million deal, Turner brings elite rim protection and three-point shooting to Milwaukee’s frontcourt. At 29, the former Indiana Pacers center is in his prime, averaging 15.6 points, 6.5 rebounds, and 2 blocks per game last season while anchoring a Pacers team that reached the NBA Finals. His ability to stretch the floor (career 35% from three) and protect the paint complements Giannis’s relentless drives and defensive versatility. Together, they form a fearsome defensive duo capable of shutting down opponents’ interior attacks while spacing the floor offensively. This move, orchestrated by GM Jon Horst, signals Milwaukee’s intent to maximize Giannis’s prime and address their defensive shortcomings, especially after losing Brook Lopez to the LA Clippers.
However, the Bucks’ roster still has a glaring weakness: perimeter scoring and playmaking. Without Lillard, Milwaukee lacks a dynamic guard to create offense and alleviate pressure from Giannis. According to Sam Amico of Hoopwire, the Bucks are targeting Boston Celtics guard Anfernee Simons, a 25-year-old scoring dynamo acquired by Boston in a June trade that sent Jrue Holiday to the Portland Trail Blazers. Simons, on an expiring $27.7 million contract, averaged 19.3 points, 4.8 assists, and 2.7 rebounds last season, with shooting splits of 42.6% from the field, 36.3% from three, and 90.2% from the free-throw line. His back-to-back seasons of over 20 points per game (peaking at 22.6 in 2023-24) showcase his ability to light up the scoreboard, making him an ideal fit to fill Milwaukee’s offensive void.
The potential trade for Simons is not without complications. Boston, grappling with luxury tax constraints and Jayson Tatum’s Achilles injury, is actively shopping Simons to shed salary, though they may retain him if no suitable deal emerges. For Milwaukee, acquiring Simons would likely require parting with valuable assets, possibly including forward Bobby Portis or draft picks, which are already scarce after years of aggressive roster moves. Portis, a fan favorite and key bench scorer, would be a tough loss, but Simons’s youth, athleticism, and long-range shooting could transform the Bucks’ backcourt. Pairing him with Giannis and Turner could create a balanced attack, with Simons handling the ball and stretching defenses, Turner spacing the floor, and Giannis dominating inside and out.
The risks are significant. Simons, while a prolific scorer, is not the playmaker Lillard was, and his defensive limitations could strain Milwaukee’s system under coach Doc Rivers. Additionally, his expiring contract poses a long-term question: can the Bucks re-sign him, or will they lose him in 2026 free agency? On the flip side, the upside is tantalizing. At 25, Simons is entering his prime and could grow alongside Giannis, who remains the Bucks’ cornerstone. The Eastern Conference, with Boston weakened by Tatum’s injury and other contenders like the Pacers facing their own challenges, may be more open than ever, giving Milwaukee a window to strike.
The Bucks’ offseason moves reflect a high-stakes strategy. Waiving Lillard’s $113 million contract and signing Turner was a bold pivot, but it came at the cost of $22.5 million in dead cap space annually through 2029-30—a gamble that has drawn skepticism from rival executives. Some argue Milwaukee is trading one bad situation for another, replacing Lopez’s veteran presence with Turner’s youth but tying up future cap flexibility. Yet, with Giannis reportedly monitoring the team’s direction, these moves demonstrate Milwaukee’s commitment to contending now. Adding Simons could be the final piece to restore the Bucks’ championship aspirations, but it hinges on Horst’s ability to navigate the trade market without depleting the roster further.
The Milwaukee Bucks stand at a pivotal moment. The addition of Myles Turner has reinvigorated their defense, pairing him with Giannis Antetokounmpo to form a frontcourt that could dominate the East. Pursuing Anfernee Simons signals their ambition to address their offensive shortcomings and rebuild a contender around their superstar. While risks abound—Simons’s fit, the cost of the trade, and the long-term cap implications—the potential reward is a revitalized Bucks team ready to reclaim their place among the NBA’s elite. Will Milwaukee pull off this blockbuster trade and return to glory, or will they fall short in their quest to satisfy Giannis’s championship hunger? The 2025-26 season looms as a defining chapter. What do you think—can the Bucks make it work with Turner and Simons?