As the 2025-26 NBA season looms on the horizon, the Boston Celtics find themselves at a crossroads. With a roster still brimming with talent, they have the potential to compete for a playoff spot in the fiercely competitive Eastern Conference. However, whispers around the league suggest this could be a season better spent focusing on the long game—prioritizing the health of their stars and the growth of their young core rather than chasing short-term glory. Unfortunately, one costly misstep from the front office threatens to derail their plans entirely: the acquisition of Anfernee Simons, a guard whose massive contract could haunt Boston for years to come.
In a move that raised eyebrows across the NBA, the Celtics acquired Anfernee Simons from the Portland Trail Blazers in a straight-up swap for veteran guard Jrue Holiday. Initially, draft picks were rumored to be part of the deal, but those were scrapped after Holiday’s physical with Portland’s medical staff. The trade left Boston with a shiny new toy—and a hefty $27.6 million bill for the upcoming season. On paper, Simons, a high-flying scorer with a knack for highlight-reel plays, seemed like a bold addition. In reality, his fit with the Celtics is questionable at best, and his contract could prove to be a financial albatross.
Simons’ $27.6 million salary for the 2025-26 season is a steep price for a player who has yet to prove he can contribute to a winning team, let alone anchor one as a primary option. Since becoming a part-time starter in Portland during the 2021-22 season, Simons’ performance has trended downward. His per-game averages have slipped, and his shooting efficiency has taken a hit. Known for his volume-shooting tendencies, Simons boasts a concerning 2-to-1 assist-to-turnover ratio, signaling he’s far from the playmaking floor general the Celtics need.
Under head coach Joe Mazzulla, Boston’s offense thrives on ball movement, discipline, and defensive versatility—qualities Simons has yet to consistently display. Allowing him to dominate the ball with 18 shot attempts per game would disrupt the team’s carefully crafted identity and likely leave them short of playoff contention. At the same time, his presence makes it unlikely the Celtics will bottom out enough to secure a high pick in the highly anticipated 2026 NBA Draft, a class projected to be loaded with generational talent.
The Celtics’ predicament is a classic case of NBA purgatory: not good enough to compete with the East’s elite, not bad enough to rebuild through the draft. General manager Brad Stevens, known for his shrewd decision-making, surely recognizes the danger of this limbo. Yet, unloading Simons’ contract may prove easier said than done. After more than a month on the trade market, there’s been little buzz about potential suitors. Teams are wary of taking on a $27.6 million salary for a player whose production doesn’t match his paycheck, especially when his skill set screams “volume scorer” rather than “difference-maker.”
The acquisition of Anfernee Simons could go down as one of the costliest mistakes in recent Celtics history. His bloated contract risks anchoring the team to mediocrity, draining resources that could be better spent developing young talent or pursuing players who align with Boston’s championship aspirations. Without a trade partner willing to take a gamble on Simons, the Celtics may be forced to ride out the season with a player who, at best, serves as an expensive seat warmer.
As the new season approaches, Boston fans can only hope Stevens finds a way to course-correct before Simons’ contract becomes a $100 million anchor, dragging the franchise’s future into the depths of NBA irrelevance.