The Portland Trail Blazers pulled off one of the most surprising trades of the offseason, sending Anfernee Simons to the Celtics for Jrue Holiday. Portland also initially agreed to send two second-round picks to Boston, but the trade was later amended due to Holiday's medical records. It was a Simons-Holiday swap.
The Celtics trading Holiday wasn't surprising, not after Jayson Tatum ruptured his Achilles in the playoffs and changed Boston's trajectory. What nobody expected was for Portland to trade for Holiday (again). The Trail Blazers aren't contenders, so they seemingly traded for the 35-year-old for him to be a leader in a young locker room.