From the frustration of endless losing in Portland to finally tasting real contention in Boston, Anfernee Simons‘ journey has come full circle—and it’s paying off in the best way possible. After years of pleading for “the opportunity to win” during his Trail Blazers tenure—highlighted by his raw honesty in the 2024 exit interview following a dismal 21-win season—Simons has landed exactly where he needed to be: on a legitimate Eastern Conference powerhouse with the Boston Celtics.
Dec 28, 2025; Portland, Oregon, USA; Boston Celtics guard Anfernee Simons (4) and Portland Trail Blazers guard Damian Lillard (0) meet after the game at Moda Center. Mandatory Credit: Soobum Im-Imagn Images
The move happened this past summer (July 7, 2025), when Boston sent veteran point guard Jrue Holiday (along with a trade exception and assets) to Portland in exchange for Simons and additional picks. Initially viewed as a salary dump for the Celtics (who were shedding costs after Jayson Tatum’s Achilles tear in the prior playoffs), the deal looked like Simons might be a short-term rental. Boston’s front office quickly explored flipping him, with early rumors linking him to teams like the Clippers or Bulls for frontcourt help. But halfway through the 2025-26 season, the narrative has flipped dramatically.
The Celtics, expected to take a step back without Tatum (still sidelined recovering from his May 2025 Achilles surgery, with no firm return date but hopeful for late-season/playoff availability), have defied the odds. Sitting at 25-15 (second in the Eastern Conference behind the surging Detroit Pistons), Boston has leaned on Jaylen Brown‘s leadership (averaging around 29+ PPG), Derrick White’s two-way mastery, Payton Pritchard’s emergence, and—crucially—Simons’ explosive bench scoring.
The 26-year-old guard, now thriving as a sixth man, has averaged roughly 14.1 points, 2.4 rebounds, and 2.6 assists in 24.3 minutes per game across 40 appearances (all off the bench), shooting an efficient 44.1% FG and 40.5% from three. His impact has been undeniable: Boston is a perfect 12-0 when Simons scores 17+ points this season, and he’s posted strong recent numbers (18.3 PPG, 4.1 threes in games since January 1). The pinnacle? His season-high 39-point explosion (13-28 FG, 7-16 3PT, 4 rebounds, 4 assists) in a thrilling 119-114 comeback win over the Miami Heat on January 15, 2026. Trailing by 19 early, Simons poured in 18 fourth-quarter points to fuel the rally, accounting for nearly 41% of Boston’s scoring in 34 minutes. It was a statement performance—his most complete as a Celtic—and a reminder of the scoring punch he brings off the pine.
This surge aligns perfectly with what Simons craved in Portland: a real shot at winning. The Blazers, committed to building around young lottery picks Scoot Henderson and Shaedon Sharpe, never fully meshed with Simons’ win-now urgency despite improving to 36 wins in 2024-25. His expiring $27.6 million contract (final year of a four-year, $100M deal) made him movable, but Boston’s unexpected rise has changed everything.
With the February 5, 2026, trade deadline approaching, Simons remains a trade candidate—his salary is a valuable expiring deal for acquiring a big man (rumors link him to targets like Ivica Zubac, Nic Claxton, or others to bolster the frontcourt). Defensive concerns (he’s still targeted in matchups) and the impending return of Tatum (who could limit bench minutes) fuel the chatter. Yet insiders note Boston might keep him: He’s sacrificed, produced (first bench player to 100+ threes), and fits as a microwave scorer in a contending rotation. The East’s surprising weakness gives Boston a legitimate Finals path if Tatum returns in time—Simons could be key to that run.
For a player who endured years of rebuilding pain, this is vindication. Simons is no longer just hoping for contention—he’s living it, dropping 30+ bombs and helping steer the Celtics toward another deep playoff push. If Boston holds on (and Tatum’s rehab continues positively), the “Anferno” off the bench could be the X-factor that delivers the opportunity he’s chased since Portland. Celtics fans, enjoy the ride—Simons is finally winning, and the Green are rolling.