The Boston Celtics are trading veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two future second-round draft picks, according to multiple sources familiar with the deal. The trade helps the Celtics significantly lower their projected luxury tax bill by shedding the final two years of Holiday’s contract, which is worth approximately $72 million. While Holiday played a key role in Boston’s recent championship run, the move reflects the team’s shift toward financial flexibility and long-term roster planning.
Holiday, known for his elite perimeter defense and steady leadership, now returns to Portland after briefly landing there in 2023 as part of the Damian Lillard trade. He was quickly moved to Boston at the time, where he became a valuable contributor to their title-winning season. Now, Portland will likely benefit from his veteran presence as it looks to guide a young roster in a rebuilding phase. On the other side of the deal, Boston adds 26-year-old guard Anfernee Simons, a proven scorer with strong three-point shooting ability, making him a good fit for coach Joe Mazzulla’s fast-paced offensive system.
This trade signals the start of what could be a busy offseason for the Celtics, especially as they look to retool the roster following Jayson Tatum’s Achilles injury. With Holiday gone and uncertainty around Tatum’s recovery timeline, Boston may continue exploring ways to balance immediate competitiveness with long-term cap management. Meanwhile, Portland secures a respected veteran in Holiday, who could either anchor their backcourt or become a valuable trade asset as the season progresses.
