Celtics, Blazers Agree to Swap Jrue Holiday and Anfernee Simons in Blockbuster Trade

Holiday is off to Portland.

Boston Celtics guard Holiday reacts after a play during the second against the Orlando Magic at TD Garden. | Bob DeChiara-Imagn Images

The Boston Celtics have agreed to trade Jrue Holiday to the Portland Trail Blazers in exchange for guard Anfernee Simons and two second-round picks, according to a Monday night report from ESPN NBA insider Shams Charania.

The Blazers acquired Holiday in the trade that sent Damian Lillard to the Milwaukee Bucks, but later sent him to Boston for draft capital. Holiday won an NBA title with the Celtics in 2024.

Simons, meanwhile, joins Boston with just one year remaining on his contract. He averaged 19.3 points and 4.8 assists for the Blazers last season while shooting 36.3% on three-pointers.

BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT

— Shams Charania (@ShamsCharania) June 24, 2025

Holiday, a two-time All-Star, averaged 11.1 points, 4.3 rebounds and 3.9 assists for the Celtics in 62 games last season, all of which were starts. He has received NBA All-Defensive honors six times, having been named first-team and second-team All-Defense three times apiece.

It's a massive roster shakeup for the '24 champions, which Charania quickly noted may see even more overhaul.

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