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Anticipating a transformative offseason, Boston has initiated the process of revamping its championship-caliber roster. The Celtics have reportedly traded seasoned point guard Jrue Holiday to the Portland Trail Blazers in exchange for promising scorer Anfernee Simons and a pair of second-round draft picks.
Celtics receive:
Trail Blazers receive:
BREAKING: Jrue Holiday has been traded from the Boston Celtics to the Portland Trail Blazers for Anfernee Simons and two second-round picks, according to sources speaking with ESPN. pic.twitter.com/2ycXQicGkT
— Shams Charania (@ShamsCharania) June 24, 2025
Holiday, now 35, contributed to Boston for two seasons, playing a key role in their clinching of the 18th championship during the 2023-24 season, but they faced a setback in the second round against the New York Knicks this spring, due to Jayson Tatum’s torn Achilles injury.
This injury, along with concerns over Boston’s escalating payroll, sparked discussions about moving some of their high-salaried veterans. Notably, Charania also indicated that the Celtics are in discussions involving other unnamed players.
Interestingly, Holiday was a Trail Blazer for a brief period after his involvement in the Milwaukee trade for Damian Lillard in 2023, prior to his acquisition by Boston just days later. The Celtics secured another championship within a year, largely owing to Holiday’s tenacious defense and team-oriented play.
Meanwhile, Simons has emerged as a solid scoring option during his seven years with Portland, consistently averaging at least 17.3 points per game over the last four seasons.
At 26 years old, he boasts a shooting percentage of 38.1% from beyond the arc on an average of 6.5 attempts per game, making him an ideal fit for an aggressive Celtics squad that topped the league in three-pointers made and shot attempts last season.
While Boston will feel the impact of Holiday’s defense and veteran leadership, his scoring output had dropped, averaging only 11.1 points last season—his lowest since his rookie year in 2009-10—and over eight points lower than his 19.3 points per game during the 2022-23 season with the Bucks, when he was selected as an All-Star.
Additionally, it’s likely that the Celtics were prompted to trade Holiday due to the $104.4 million remainder of his contract over the next three years, compounded by the substantial contracts for Tatum and Jaylen Brown.
According to Bobby Marks of ESPN, this trade is expected to result in approximately $40 million in tax savings for the Celtics.
Here are the outgoing salaries:
To Boston
Anfernee Simons: $25.9M, $27.7M (UFA, 2026)
* The Celtics shed the combined $72M owed to Holiday for the 2026-27 and 2027-28 seasons.
* Anticipated $40M in tax savings for the 2025-26 season.
* $18M under the second apron.
* Simons is eligible for an extension.
To…
— Bobby Marks (@BobbyMarks42) June 24, 2025
Holiday, instrumental in securing the 2021 NBA championship for the Bucks, has averaged 15.8 points per game throughout his 16-year career, which includes time with the Philadelphia 76ers and the New Orleans Pelicans.
This report has utilized information from The Associated Press.
