The Boston Celtics are reportedly actively trying to trade Anfernee Simons after acquiring him from the Portland Trail Blazers in the deal that sent Jrue Holiday west, as the franchise continues efforts to shed salary and reshape the roster following an eventful offseason. Simons, who arrives on a $27.7 million expiring contract, was part of a revised player-for-player swap after a review of Holiday’s medical history led to the removal of previously included draft compensation. With the Celtics approximately $20 million over the luxury tax and Jayson Tatum sidelined due to a torn Achilles, Boston is prioritizing financial flexibility and long-term roster stability.
ESPN’s Brian Windhorst revealed on The Hoop Collective Podcast that teams around the league have indicated the Celtics are “actively” exploring options to flip Simons elsewhere. While it remains uncertain whether a deal will materialize, Boston’s motivation is clear—trading Simons would significantly ease luxury tax pressures, especially after already moving Kristaps Porziņģis and Holiday, whose contract includes $72 million in guaranteed salary beyond this upcoming season. Simons, represented by agent Bill Duffy, may offer value to teams in need of scoring depth, though his injury history could complicate trade talks.
The 26-year-old guard had a standout 2023-24 campaign for Portland, averaging 19.3 points, 4.8 assists, and 3.1 made threes per game, though he missed 36 contests due to thumb and knee injuries. Despite his scoring upside and career 38.1% mark from beyond the arc, Simons has been limited by durability issues, having surpassed the 70-game threshold just twice in seven seasons. Still, over the past four years, he has consistently delivered efficient offensive output with averages of 19.9 points, 4.5 assists, and 3.2 made threes across 235 games.
The Celtics’ interest in retaining Sam Hauser—despite his own tradeable four-year, $45 million contract—further underscores their commitment to reshaping the cap sheet without sacrificing core shooting depth. Boston saved roughly $40 million in projected tax payments by trading Holiday for Simons, whose value now lies as a movable contract and potential bench scorer for other teams. Holiday, for his part, departs Boston after a championship-winning season where he averaged 11.1 points and shot a career-best 42.9% from deep while earning All-Defensive honors.
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Simons, originally selected 24th overall in 2018, never played fewer than 20 games in any of his first seven seasons but has only started 213 of 389 career contests. He became a primary scoring option following Damian Lillard’s exit from Portland and has taken nearly nine three-pointers per game over the past three seasons. The Celtics, now without Tatum for most of the year, may prefer a more balanced rotation and additional defensive presence in the backcourt, which Simons does not provide at a high level.
While the Trail Blazers’ acquisition of Holiday was short-lived—they flipped him before he played a game—his medical evaluations slightly altered the final trade terms. Nonetheless, Boston’s goal remains focused: offload Simons, manage payroll, and retool for the long haul. Whether they can find a suitable trade partner for Simons remains to be seen, but the intent to move him signals that the Celtics’ offseason plans are far from finished.
