The Milwaukee Bucks, once the NBA’s juggernaut with a 2021 championship, have stumbled into mediocrity, plagued by three consecutive first-round playoff exits. At 48-34 last season—their worst winning percentage since 2017-18—the Bucks are in flux, desperate to reclaim their elite status. Enter Myles Turner, a free-agency coup whose rim-protecting prowess pairs perfectly with Giannis Antetokounmpo’s two-way dominance, forming a defensive fortress. But with Damian Lillard gone, Milwaukee’s backcourt lacks scoring punch. Enter Anfernee Simons, the 25-year-old Celtics guard on the trade block after Boston’s Jrue Holiday swap, per Sam Amico of Hoopwire. With Simons’ 19.3 PPG and 36.3% three-point shooting, could he be the offensive spark to reignite the Bucks’ title chase? Let’s unpack this potential trade, its fit with Milwaukee’s roster, and whether it can reverse their slide.
Giannis Antetokounmpo #34 of the Milwaukee Bucks reacts to a score during the second half of a game against the Portland Trail Blazers at Fiserv Forum on November 26, 2023 in Milwaukee, Wisconsin.
1. Milwaukee’s Fall from Grace: A Franchise at a Crossroads
The Bucks’ 2021 title, powered by Giannis Antetokounmpo’s 35.2 PPG in the Finals (ESPN), feels like a distant memory. Three straight first-round exits—2023 to Miami (4-1), 2024 to Indiana (4-2), and 2025 to Cleveland (4-3)—exposed cracks in Milwaukee’s armor. Last season’s 48-34 record, a .585 winning percentage, was their lowest since 2017-18 (44-38, .537), when they fell to Boston in seven games (NBA.com). The departure of Damian Lillard, traded to Portland in a 2025 blockbuster, left a void in the backcourt; his 24.3 PPG and 7.0 APG (2024-25) were critical to Milwaukee’s 7th-ranked offense (115.2 ORTG).
Giannis remains a force—28.7 PPG, 11.6 RPG, 6.5 APG on 61.1% FG in 2024-25—but the Bucks’ 20th-ranked defense (112.8 DRTG) and lack of secondary scoring (Khris Middleton: 15.1 PPG, 43.2% FG) crippled them. Myles Turner’s signing (3.2 BPG career, StatMuse) bolsters the paint alongside Giannis (1.2 BPG), pushing Milwaukee’s defensive ceiling toward top-10. Yet, the backcourt—Pat Connaughton (5.6 PPG, 41.7% FG) and AJ Green (4.5 PPG)—lacks firepower. X fans lament: “No Dame, no hope—Bucks need a scorer!” Simons, with his 19.3 PPG and 90.2% FT, could be the answer.
2. Anfernee Simons: The Scoring Spark Milwaukee Needs
\Anfernee Simons, acquired by Boston in the June 2025 Jrue Holiday-to-Portland trade, is a 25-year-old scoring dynamo. Last season, he averaged 19.3 PPG, 4.8 APG, and 2.7 RPG on 42.6/36.3/90.2 shooting splits over 32.7 MPG (ESPN). His back-to-back 20+ PPG seasons (22.6 PPG in 2023-24, 21.1 PPG in 2022-23) showcase his growth from a 2018 first-round pick (No. 24) to a high-volume shooter (1.12 PPP in isolation, top-15 guards, Synergy Sports). His 36.3% 3PT on 7.8 attempts fits Milwaukee’s spacing needs, especially with Giannis’ paint dominance (14.2 points in paint per game).
Simons’ $27.7M expiring contract makes him a trade target for Boston, who are $199M over the second apron and shedding salary after extensions for Tatum ($239M) and Brown ($304M) (Spotrac). Milwaukee, at $174M, has cap flexibility to absorb Simons via trade, potentially offering Brook Lopez ($23M, expiring) and draft picks. Simons’ 1.08 PPP in pick-and-rolls (top-20 guards) would thrive with Giannis’ rolls (1.14 PPP) and Turner’s pops (38.1% 3PT career). X hype: “Simons to Bucks? Giannis just got a new best friend!” Concerns? His 4.2 DRTG (bottom-20 guards) could strain Milwaukee’s defense, though Turner and Giannis mitigate blow-bys.
3. The Trade Landscape: Can Milwaukee Outbid Rivals?
Boston’s urgency to move Simons stems from their cap crunch—$199M payroll risks frozen 2032 picks and trade bans (ESPN). Amico notes the Celtics aren’t locked into trading Simons; his youth (25) and 4.8 APG could fit their Tatum-less 2025-26 start (Achilles injury, out until April). But with Derrick White (16.2 PPG) and Payton Pritchard (9.6 PPG) holding the backcourt, Simons is expendable. Milwaukee’s competition includes teams like the Lakers, per Hoopswire (September 18), who could offer D’Angelo Russell ($18.7M) and a 2029 first-rounder. The Bucks’ edge? A stronger package with Lopez, a 2027 first (top-8 protected), and MarJon Beauchamp (5.1 PPG, 22 years old).
Lopez, a 2023 All-Defensive pick (2.5 BPG), gives Boston frontcourt depth behind Al Horford, while the pick and Beauchamp add future value. Milwaukee keeps Middleton and Bobby Portis (13.8 PPG), preserving their core. The trade could look like: Simons to Bucks for Lopez, Beauchamp, a 2027 first, and a 2028 second. X poll: 71% say “Simons makes Bucks contenders.” Risks? Simons’ expiring deal requires a $30M+ extension, and his 2.8 turnovers per game could disrupt Milwaukee’s 12th-ranked turnover rate (12.9%). But his scoring ceiling outweighs the gamble.
4. Bucks’ Title Path: Simons, Giannis, and Turner as the New Big Three
Milwaukee’s 48-34 record and 8th seed last season screamed regression, but Turner’s arrival (projected 10.5 PPG, 7.0 RPG, 2.8 BPG) and Simons’ potential add firepower. Giannis’ 28.7 PPG and 1.14 PPP in transition (top-5) pair with Simons’ 1.12 isolation PPP for a dynamic offense, potentially pushing Milwaukee’s ORTG to top-5 (from 115.2). Turner’s 38.1% 3PT opens the floor, and his 3.2 BPG career average complements Giannis’ 1.2 BPG, forming a defensive wall (projected top-8 DRTG, Cleaning the Glass). Coach Doc Rivers, who led the 2021 title, can leverage Simons’ pull-up threes (37.4% on 5.2 attempts) in clutch moments, where Milwaukee ranked 18th (1.02 PPP).
The East is brutal—Boston (even without Tatum), Philly (Embiid healthy), and Cleveland (46-36 in 2025) loom—but Milwaukee’s projected 50-52 wins (ESPN BPI) signal a rebound. Simons’ youth ensures longevity beyond Giannis’ prime (31 in 2025). X buzz: “Giannis + Turner + Simons = 2021 vibes!” Challenges include Simons’ playoff inexperience (17.1 PPG, 41.2% FG in 2023) and Middleton’s knee issues (missed 27 games in 2024-25). If Milwaukee lands Simons, their ceiling is a Conference Finals run, their first since 2021.
The Milwaukee Bucks, reeling from three playoff flops, see Anfernee Simons as the scoring jolt to complement Giannis Antetokounmpo and Myles Turner. His 19.3 PPG and 36.3% 3PT could restore Milwaukee’s offensive edge, while a trade package of Lopez and picks aligns with Boston’s cap needs. As the Bucks chase their 2021 glory, Simons could be the key to a deep playoff push. Bucks Nation, is Simons the missing piece for another ring, or a risky bet?