A surprising late-night NBA trade saw Jrue Holiday sent from the Boston Celtics to the Portland Trail Blazers in exchange for Anfernee Simons and a pair of future second-round picks. With the 2025 NBA offseason in full swing, here’s how both teams graded out following the move.
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Trade Details
Boston Celtics receive:
- Anfernee Simons (G, 26)
- Two future second-round picks
Portland Trail Blazers receive:
- Jrue Holiday (G, 35)
Boston Celtics Trade Grade: A
Salary Relief, Roster Flexibility & Value Return
With the Celtics well over the NBA’s second apron, shedding salary was a top priority—especially after Jayson Tatum’s Achilles injury removed the team from championship contention next season. Trading Holiday clears significant salary from the books, saving over $40 million for the 2025–26 season.
Why It Works
- Simons, 26, is a young sharpshooter (19.3 PPG, 36.3% 3PT) entering a contract year, making him a low-risk addition.
- Boston adds draft capital that can be flipped for future deals.
- Clears a path for flexibility without long-term commitments.
- Brad Stevens extracted value from a move many saw as desperate.
Bottom Line: The Celtics turned a financial problem into an opportunity. They freed up cap space and got a productive player in return—an excellent outcome given the circumstances.
Portland Trail Blazers Trade Grade: B-
A Veteran for the Youth Movement?
On the surface, trading a 26-year-old scorer for a 35-year-old veteran—while adding draft picks—raises eyebrows. But Portland may be focused on changing its identity, transitioning from offense-first to defensive-minded basketball.
Roster Balance & Leadership
- Jrue Holiday brings elite defense, leadership, and championship experience.
- Helps shape a young backcourt of Scoot Henderson and Shaedon Sharpe.
- Blazers finished top 10 in defense post-All-Star break; Holiday fits that trend.
Overpay?
- Giving up two second-round picks in addition to Simons may have been unnecessary.
- Holiday is under contract for three more years at $134 million—a risky deal if age catches up.
Bottom Line: While Simons may be a better long-term asset, Portland gets a floor general to stabilize the team and set a winning tone. Still, the price—especially including picks—was a bit steep.
Final Verdict: Who Won the Trade?
Winner: Boston Celtics
Boston needed financial relief and flexibility, and they got it—without sacrificing leverage. Simons gives them youth, shooting, and options for future moves.
Portland’s Outlook: Mixed but Understandable
The Blazers’ decision reflects a commitment to defensive identity and veteran leadership, even if the trade wasn’t a steal on paper. If Holiday helps instill winning habits, it may pay off in intangible ways.
Trade Grades Summary
| Team | Grade | Key Takeaways |
|---|---|---|
| Boston Celtics | A | Cleared cap space, got a productive shooter + 2 picks |
| Portland Blazers | B- | Added leadership and defense, but likely overpaid |