Anfernee Simons expressed his frustration at the end of Portland’s dismal 2024 campaign, stating, “We don’t want to have another year like this… I want the opportunity to win.” After six seasons with the Trail Blazers and a mere 21 wins in 2024, his desire for change was clear.
By January 2025, Simons was candid about the toll losing had taken on him, telling The Athletic he was enduring the toughest mental stretch of his career. “Not winning as much as you would like… it can get on you mentally,” he admitted, as Portland sat at 11-22 one of the league’s worst records at the time.
Although the Blazers showed late-season improvement, ending 2025 at 36-46, the progress likely fell short of Simons’ aspirations. Now, joining the title-contending Boston Celtics, he finally finds the competitive environment and organizational consistency he’s long sought.
Blazers Trade Anfernee Simons to Celtics, Putting Him in Prime Position to Win
In a move that swapped offensive firepower for defensive reliability, the Portland Trail Blazers traded Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday. While Holiday is widely regarded as the more impactful player, Boston’s decision was driven in part by a desire to stay below the league’s punitive second tax apron making this deal a potential win-win for both franchises.
Initially, there was speculation that the Celtics might flip Simons to address roster balance, especially after parting ways with multiple frontcourt players this offseason. However, with Simons on an expiring contract, rival teams have been hesitant to offer significant assets in return, increasing the likelihood that he stays in Boston for now.
Despite Jayson Tatum’s Achilles injury and the absence of Holiday and Kristaps Porzingis, Simons enters a wide-open Eastern Conference with a legitimate chance to compete. While the Cavaliers and Knicks are early favorites and the Magic are gaining momentum following the Desmond Bane acquisition, each contender has noticeable roster flaws leaving Boston with a real shot.
Simons’ skill set aligns well with head coach Joe Mazzulla’s offensive system, which led the NBA in three-point attempts last season. If he can adapt to a sixth-man role behind Payton Pritchard and Derrick White, there’s even a chance Boston considers keeping him long-term.
Although his future in Boston remains uncertain, one thing is clear: the Blazers finally delivered on Simons’ long-standing desire to play for a winning franchise.
