Jrue Holiday is returning to the Western Conference after spending the last five years of his career with Boston and Milwaukee. The Celtics traded the two-time champion to the Trail Blazers in exchange for Anfernee Simons and two second-round draft picks on Monday, June 23rd, 2025, just one day after the NBA Finals concluded. Holiday will make $32.4 million next season, and his current deal will only become more expensive.
He missed out on an All-Defensive Team selection this past season—the first time since 2020. Going into a season where he will be 35 years old, Boston decided to be proactive and move off of Holiday’s contract while adding some youth in Anfernee Simons. What will be interesting to see is whether Jrue Holiday can assist the Portland Trail Blazers in their current rebuilding phase.
Boston Celtics Trade Jrue Holiday to the Portland Trail Blazers
Trail Blazers Likely to Retain Jrue Holiday
Portland’s motivation for trading for Jrue Holiday remains questionable. However, the Trail Blazers appear willing to keep him and believe he could be a solid piece for their developing core of young talent. Portland did have the fourth-best defense down the stretch of the regular season. The Trail Blazers could be thinking that Holiday’s championship experience and defensive pedigree will be instrumental in their quest to return to playoff contention.
Moreover, the team is hoping Holiday can serve as a valuable voice in the locker room due to his veteran leadership and championship background. Still, this move is puzzling considering how expensive Holiday’s contract is, especially in light of the youth movement the Trail Blazers have been emphasizing since last season. While there could be some benefits to bringing in a veteran like Holiday, it seems like the Boston Celtics got the better end of this deal.
Celtics Could be Looking to Reset for a Year
With Jayson Tatum likely to miss next season, the Celtics may be looking to do a soft reset. Offloading Holiday’s contract is a massive weight off the team’s proverbial shoulders. Furthermore, acquiring a young talent like Anfernee Simons gives their offense a new dimension while also allowing them to get younger.
Simons is on an expiring $27.7 million contract, providing Boston with flexibility for the future. They can either let him walk after next season, use him in a future deal, or even keep him if he shines during his time in Boston. After all, Simons did average 19.3 points per game along with 4.8 assists per contest last season. Considering all of this, the Celtics seem to be the winners of this trade as of now.
