Jrue Holiday is headed to Portland.
The Trail Blazers struck a deal with the Boston Celtics on Monday night to acquire Holiday, according to ESPN’s Shams Charania. In exchange, Portland is sending Boston Anfernee Simons and a pair of future second-round draft picks.
Holiday spent the past two seasons with the Celtics, and he played a key role in their NBA championship run in 2024. Holiday averaged 11.1 points and 4.3 rebounds per game last season, his 16th in the league. The 35-year-old landed in Boston after the Trail Blazers dealt him there following the Damian Lillard trade to the Milwaukee Bucks. Holiday didn’t play a game for Portland before the Trail Blazers routed him to Boston.
Holiday had two years left on his current deal with the Celtics, and he’s still owed $67.2 million with a $37.2 player option for a third year. The move to send Holiday to Portland is projected to save the Celtics about $4.7 million in salary next season and move them $18 million over the second apron.
The deal, according to Charania, is only the beginning for the Celtics this offseason. The team is still engaged in trade talks “surrounding multiple key players on the roster,” though further specifics are not yet known. The team has significant work to do to avoid the luxury tax altogether, and it’s likely that Holiday is simply the first player to go.
Simons has been a solid piece for the Trail Blazers in recent years. The franchise selected him with the No. 24 overall pick out of IMG Academy in 2018. He averaged 19.3 points and 4.8 assists per game last season, his seventh in the league. The 25-year-old signed a four-year, $100 million deal with the Trail Blazers, though he’s set to enter the final year of that contract this fall — which makes him even more appealing for the Celtics considering their financial situation. The Celtics went 61-21 last season, but they lost star Jayson Tatum to an Achilles injury that will sideline him for a good chunk of next season.
As for Portland, Holiday could make a significant impact there next season. Though he’s nearing the end of his career, he’s still a good veteran presence who could help the Trail Blazers’ young locker room as they attempt to make the postseason for the first time since 2021. That is, though, if they opt to keep Holiday around this time.
