The Boston Celtics have reportedly traded guard Jrue Holiday to the Portland Trail Blazers in exchange for guard Anfernee Simons and two second-round picks, sources with knowledge of the situation confirmed to ESPN's Shams Charania late Monday (June 23) night.
Holiday was previously traded by the Milwaukee Bucks to the Blazers as part of the three-team deal centered around Damian Lillard prior to the 2023-24 NBA season before being shipped to Boston four days later in exchange for Robert Williams III, Malcolm Brogdon and two future first-round draft picks.
"BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN," Charania wrote on his X account. "Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract."
Holiday started 69 games during the 2023-24 season and all 19 playoff games during the Celtics' NBA championship run during his first of two seasons with the franchise. The former UCLA standout averaged 11.1 points, 3.9 assists and 4.3 rebounds in 62 starts during the 2024-25 NBA season and 9.5 points, 4.0 assists and 4.1 rebounds in Boston's eight playoff starts.