Breaking: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell Shams Charania. Get breaking news alerts from Shams Charania through the ESPN…
Breaking: Jrue Holiday Traded to Portland Trail Blazers in Celtics Shake-Up
In a significant move that signals a continued reshaping of their championship roster, the Boston Celtics have traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round draft picks, according to NBA insider Shams Charania.
The deal, which broke on June 25, 2025, marks the second major trade for Boston this offseason after moving Kristaps Porzingis to Atlanta just days prior. Together, these moves shed over $60 million in salary, indicating Boston’s urgent need to reset financially amid harsh second-apron luxury tax restrictions under the NBA’s new collective bargaining agreement.
Jrue’s Short But Impactful Tenure in Boston
Holiday, 34, was a critical piece of the Celtics’ 2024–25 championship run, providing elite defense, veteran leadership, and clutch playoff performances. He arrived just last offseason in a blockbuster deal from Milwaukee and immediately filled the void left by Marcus Smart. Known for his poise and two-way play, Holiday averaged 12.5 points, 5.4 assists, and nearly 1.2 steals per game in Boston.
Despite his contributions, Holiday’s $32 million salary became a cap albatross, especially with Jayson Tatum’s supermax extension kicking in and Jaylen Brown already on a $50+ million deal. The front office clearly decided it was time to move on.
The Return: Simons and Flexibility
In return, Boston receives 26-year-old guard Anfernee Simons, a proven scorer who averaged 19.9 points per game last season with Portland. Simons, a dynamic shooter and playmaker, offers a different profile—more offensive firepower, less defense—but comes on a more manageable contract with one year left on his deal, worth roughly $24 million.
The inclusion of two second-round picks gives Boston additional flexibility in future trades or roster development. While not headline assets, these picks could be useful under a new CBA that emphasizes cost-controlled depth.
What This Means for Boston
This trade is about more than just roster construction—it’s about financial survival. The Celtics were barreling toward a projected $500+ million payroll for 2025–26, which would have smashed through the league’s second apron. That would’ve restricted nearly all transaction flexibility, from signing buyout players to including cash or picks in trades.
By moving Holiday and Porzingis, Boston lowers its tax bill and gains the ability to reshape around a younger, cheaper core while Tatum recovers from a torn Achilles tendon. Sources around the league suggest that additional moves may be on the horizon, with interest in Jaylen Brown and Derrick White reportedly “significant.”
Portland’s Perspective
For the Blazers, acquiring Holiday is about injecting stability into a young locker room. They hope Holiday can serve as a mentor to rising stars Scoot Henderson and Shaedon Sharpe, while also potentially being flipped later in the season for more assets if the rebuild continues.
Final Thoughts
This trade is emblematic of the harsh financial realities facing contending teams under the new CBA. Boston fans may be shocked to see key championship contributors depart, but the long-term strategy is clear: recalibrate now, remain competitive, and return to contention once Tatum is healthy and the books are cleaner. More moves are likely coming.
