NBA TRADE: Late Night Deal Sends Jrue Holiday to Unexpected Destination

The Boston Celtics are in dire need of getting under the second apron in order to get their financial house in order and be able to move forward with roster construction into the future. With that, they have pulled off a late-night trade with the Portland Trail Blazers, sending six-time All-NBA Defensive Team guard Jrue Holiday out west in exchange for Anfernee Simons.

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

Boston also gets two second-round picks in the deal.

Holiday was a critical part of the Celtics' 2024 championship run, but at age 35, and with three years to go on his contract with his $34 million+ AAV, he was the most sensible first move for Boston to get under the second apron of the luxury tax thresholds.

More moves will likely be coming for them, with Kristaps Porzingis a possible next piece to go.

More to come…