The Milwaukee Bucks, once a towering force in the NBA, have stumbled in recent years, their 2021 championship glow dimmed by three consecutive first-round playoff exits. The team that once dominated with Giannis Antetokounmpo leading the charge is now at a crossroads, searching for a spark to reignite their contender status. With a bold offseason move already in the books—signing Myles Turner to form a formidable defensive tandem with Giannis—the Bucks are reportedly eyeing another blockbuster addition to shake up their roster.
According to Sam Amico of Hoopwire, Milwaukee is setting its sights on Boston Celtics guard Anfernee Simons, a dynamic scorer who could be the key to solving the Bucks’ offensive woes. Simons, acquired by Boston in a June trade that sent Jrue Holiday to the Portland Trail Blazers, has been on the trade block as the Celtics look to trim their payroll. With a $27.7 million salary for the 2025-26 season—the final year of his contract—Simons represents both a financial burden for Boston and a tantalizing opportunity for Milwaukee.
The Bucks’ backcourt has been a glaring weak spot since the departure of Damian Lillard, leaving them desperate for a reliable scoring option to complement their defensive prowess. Simons, at just 25 years old, could be the answer. Last season, he averaged 19.3 points, 4.8 assists, and 2.7 rebounds in 32.7 minutes per game, shooting an efficient 42.6% from the field, 36.3% from three, and 90.2% from the free-throw line. His scoring ability isn’t a fluke either—Simons posted back-to-back seasons of over 20 points per game in 2022-23 and 2023-24, peaking at 22.6 points in the latter.
The young guard’s ability to create his own shot and stretch the floor with his three-point shooting could provide the offensive firepower Milwaukee desperately needs. Paired with the defensive wall of Giannis and Turner, Simons could help the Bucks rediscover the balance that made them champions just a few years ago.
For the Celtics, Simons is a bit of a puzzle. Boston isn’t fully committed to moving him, as the former first-round pick still has the potential to be a cornerstone of their future. However, with the team actively looking to shed salary, a trade seems more likely than not. If the right deal comes along, Simons could be on the move before the 2025-26 season tips off. Milwaukee, with its clear need for backcourt scoring, could be the perfect trade partner to capitalize on Boston’s financial maneuvering.
Milwaukee’s 48-34 record last season was their worst winning percentage since the 2017-18 campaign, when they won 44 games and fell to the Celtics in the first round. That history adds an extra layer of intrigue to this potential deal—could Simons, a former Celtic, help the Bucks flip the script on their postseason struggles? The addition of Turner already signals Milwaukee’s intent to double down on defense, but without a reliable offensive engine in the backcourt, their championship aspirations could remain out of reach.
Pursuing Simons is a high-stakes gamble for the Bucks. His $27.7 million salary is no small commitment, and with only one year left on his deal, Milwaukee would need to be confident in either re-signing him or maximizing his impact in a single season. But if the Bucks can pull off this trade, they might just find the missing piece to restore their status as NBA titans.
As the 2025-26 season looms, all eyes will be on Milwaukee and Boston to see if this deal materializes. For the Bucks, landing Simons could be the bold move that reignites their championship fire. For the Celtics, it’s a chance to offload a hefty contract while potentially reshaping their roster for the future. One thing is certain: if Milwaukee makes this move, the NBA landscape could shift dramatically.