In a significant and potentially landscape-altering move ahead of the 2025-26 NBA season, the Boston Celtics have reportedly agreed to trade veteran guard Jrue Holiday to the Portland Trail Blazers. Sources indicate the Celtics will receive guard Anfernee Simons and two second-round draft picks in return for the two-time NBA champion. The deal, expected to become official in July, marks a strategic shift for both franchises.
For the Boston Celtics, the impetus behind trading a key member of their 2024 championship squad appears largely financial and strategic. While Holiday was critical to their title run and earned All-Defensive honors, his contract, which had three years and over $104 million remaining (including a player option), represented a substantial future commitment. Trading Holiday significantly alleviates their salary cap pressure, saving the team an estimated $40 million in luxury tax payments next season alone and providing crucial flexibility as they navigate future contracts for stars like Jayson Tatum, who is recovering from an Achilles injury sustained in the 2025 playoffs. Shedding Holiday’s salary is seen as a necessary step to potentially duck the costly second luxury tax apron, with league sources suggesting this could be the first of several moves this offseason, possibly including exploring trades for other high-salary players. Beyond the financial aspect, Holiday is set to turn 36, and while still an elite defender, his offensive production saw a dip in his second season with Boston, including lower scoring (11.1 PPG) and a drop in three-point efficiency (35.3%), particularly in the 2025 postseason before a hamstring injury.
In Anfernee Simons, the Celtics acquire a younger, dynamic scoring guard. The 26-year-old averaged 19.3 points and 4.8 assists last season for Portland and boasts a career 3-point percentage of 38.1%. Known for his comfort shooting from distance, Simons’ offensive skillset appears well-suited for Coach Joe Mazzulla’s three-pointer-heavy offense, which led the league in attempts last season. Simons arrives on an expiring contract worth $27.7 million next season, offering Boston flexibility to either re-sign him long-term if he fits or gain further cap relief if they choose not to. However, Simons has historically graded as a poor defender, a stark contrast to the player he is replacing, and his time in Portland saw challenges adjusting to a full-time point guard role and a faster pace.
This trade marks Jrue Holiday’s second brief stop with the Trail Blazers organization; he was initially acquired by Portland as part of the Damian Lillard trade chain in 2023 but was quickly rerouted to Boston without playing a game for the team. This time, Portland’s motivation appears centered on acquiring veteran leadership and championship experience for their young core, particularly to mentor emerging point guard Scoot Henderson, the third pick in the 2023 draft. Trading Simons, who started 70 games last season compared to Henderson’s 10, clears a more direct path for Henderson to assume the primary ball-handling duties.
Holiday, a two-time NBA champion, three-time All-Star, and six-time All-Defensive team selection, brings a proven defensive identity and invaluable guidance to Portland’s developing roster. The Blazers finished last season with a 36-46 record, and Holiday’s defensive prowess could aid their efforts on that end, potentially pairing well with players like Toumani Camara and Deni Avdija. However, taking on Holiday’s substantial, aging contract for what is primarily framed as a mentor role at Henderson’s position raises questions about the Blazers’ long-term strategy and financial flexibility. Some speculation suggests the Blazers might not be done dealing and could potentially explore trading Holiday again to a contending team, or that this move signals an perhaps ambitious attempt to push towards playoff contention sooner than expected. Simons was the longest-tenured Blazer before this trade, and his departure concludes a seven-year run with the team that saw periods of high scoring but also inconsistency and injury.
The exchange of Holiday for Simons and draft compensation represents a calculated gamble for both sides – Boston prioritizing financial flexibility and youth with scoring potential, while Portland targets veteran leadership and defensive identity to accelerate the development of their young prospects. The full implications of this unexpected swap will unfold in the coming seasons.
