Boston, June 24, 2025 – In a significant roster shake-up, the Boston Celtics have shipped veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for sharpshooter Anfernee Simons and two future second‑round draft picks, as first reported by ESPN and confirmed by league sources.
The Trade Details
- To Portland: Jrue Holiday (35), still under contract through 2027‑28, earning $32.4 million next season—totaling approximately $72 million over the final two years.
- To Boston: Anfernee Simons (26) on an expiring contract, a proven perimeter scorer, plus two future second‑round picks.
Why Boston Made the Move
- Luxury tax relief – The trade generates roughly $40 million in luxury-tax savings, crucial given Jayson Tatum’s season‑ending Achilles injury.
- Financial flexibility – Simons’ expiring deal and younger age offer Boston roster flexibility and room to maneuver ahead of free agency or additional trades.
- Offensive injection – Simons averaged around 19–20 points per game last season with solid three-point efficiency (~ 38%)—a needed boost for Boston’s perimeter offense .
For Portland: Experience and Leadership
Portland reacquires Holiday for the second time—originally acquired in 2023 before his trade to Boston. The veteran all‑defensive guard brings leadership and defensive grit to a youthful roster—including Scoot Henderson and Shaedon Sharpe
Holiday’s defensive pedigree—six-time All‑Defensive—will be key as Portland aims to end its playoff drought. Financially, taking on his long-term contract signals a fresh leadership-first approach .
Strategic Implications
- Boston clears significant cap space, positioning themselves under the second tax apron—opening the door to further trades this offseason.
- Portland gets a veteran upgrade at point guard and a mentor for their developing stars, although the move may signal several more adjustments as the rebuild evolves .
Final Takeaways
This trade marks a major pivot for both franchises:
- Celtics focus on flexibility and retooling around Jayson Tatum’s injury, injecting scoring and managing finances.
- Blazers aim for leadership and defensive toughness as they nurture their young core.
As both teams gear up for free agency and the draft, expect this deal to be the spark of a busy offseason.
