The Portland Trail Blazers have acquired point guard Jrue Holiday in a trade with the Boston Celtics, sending guard Anfernee Simons and two second-round draft picks to Boston on June 24, 2025. This Jrue Holiday trade to Trail Blazers took many by surprise, as confirmed by reports from Shams Charania of ESPN.

Player Profiles and Recent Performance

Anfernee Simons, 26, is entering the final year of his contract and earned an average of 19.3 points and 4.8 assists over 32.7 minutes per game last season for Portland. Simons has been a key contributor throughout his seven years in the NBA.

Jrue Holiday, aged 35, averaged 11.1 points and 3.9 assists during 62 appearances for the Celtics last season. Holiday brings significant championship experience, having won titles with Milwaukee in 2021 and Boston in 2024.

Contract Details and Trade Background

Simons is set to make $27.7 million next season under his current deal. Holiday, on the other hand, signed a four-year extension worth $135 million in 2024. His salary is projected at $32.4 million for the next season, increasing to $34.8 million in 2026-27, with a $37.2 million player option for 2027-28.

The Blazers initially acquired Holiday in the 2023 trade that sent Damian Lillard to the Milwaukee Bucks. However, Holiday never played for Portland before being moved to Boston shortly after.

Trade Significance and Next Steps for Teams

This trade shifts the dynamic for both franchises, giving Portland a seasoned veteran in Holiday while Boston adds a younger talent with Simons plus additional draft assets. How each team integrates their new players will be key to their upcoming season strategies and overall roster development.

“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, NBA Insider