The Boston Celtics are sending veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.
ESPN’s Shams Charania shared the news via X.
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
According to Charania, Portland made a bold move to bring back Holiday, who they initially acquired from Milwaukee in the 2023 Damian Lillard trade before sending him to Boston in a deal that involved two first-round picks heading to the Blazers. Meanwhile, Simons heads to Boston on an expiring contract.
This move is the first of what could be another to come for the Celtics as they look to shed salary for next season. They finished the season as a second-apron team, and if they remain in that category, they will face severe penalties from the league.
Prior to the trade, they were projected to be nearly $500 million in roster and luxury tax next season.
It was obvious the Celtics needed to trim their roster, and Holiday was among the top candidates to be moved. Although he contributed well during his two seasons in Boston, last year wasn’t his strongest. Just a day into the NBA offseason, Holiday was shipped out of Boston.
The 34-year-old veteran guard is coming off a down year by his standards. His production dipped across the board, as he averaged 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals per game while shooting 44.3 percent from the field and 35.3 percent from three over 62 games in just 20.6 minutes of action.
His playoff performance wasn’t much better. In eight postseason appearances, Holiday posted 9.5 points, 4.1 rebounds, 4.0 assists, and 0.9 steals per contest, shooting 48.3 percent from the field and 34.6 percent from deep—numbers that fell short of expectations.
Many teams will have their eyes on Holiday, including the Sacramento Kings, Los Angeles Clippers and the Dallas Mavericks. It’s unclear if he will indeed stay in Portland, as they may want to remain in the younger route, considering how the majority of their roster looks.
Meanwhile, the Celtics add Simons, fresh off a strong season in the Pacific Northwest. Last year, he averaged 19.3 points and 4.8 assists per game. At 26 years old, Simons could quickly emerge as a key perimeter scorer alongside Jaylen Brown, especially with Jayson Tatum sidelined with his Achilles injury.
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