Anfernee Simons The NBA offseason rarely disappoints, and the Jrue Holiday trade saga is a prime example. After being dealt to the Portland Trail Blazers as part of the Damian Lillard blockbuster, Holiday didn’t stay in Rip City long. Portland flipped the veteran guard to the Boston Celtics in a deal that helped shape two franchises’ futures. With Anfernee Simons poised to step into a larger role and Boston adding a championship-caliber piece, it’s time to grade the deal from both sides.
Table of Contents of Anfernee Simons: Rising Star of the NBA
Trade Details
To Celtics:
- Jrue Holiday
To Trail Blazers:
- Malcolm Brogdon
- Robert Williams III
- 2024 first-round pick (via Golden State)
- 2029 unprotected first-round pick (Boston)
Boston Celtics Grade: A
Why It Works:
Anfernee Simons The Celtics have been chasing banner No. 18 for years, and this deal may be the piece that puts them over the top. Jrue Holiday is the epitome of a winning player: a tenacious perimeter defender, a proven leader, and an unselfish offensive contributor. In swapping out Marcus Smart (earlier in the offseason) and Malcolm Brogdon for Holiday, Boston essentially upgraded at the guard position in terms of defense, leadership, and postseason composure.
This trade also resolves several issues:
- Locker Room Stability: Holiday brings a calming presence without sacrificing toughness—something Boston has lacked at times with more volatile personalities.
- On-Ball Defense: With Derrick White and Holiday, the Celtics now arguably have the best defensive backcourt in the league.
- Clutch Performance: Holiday’s championship experience (2021 Bucks) and knack for timely plays give Boston a reliable closer alongside Jayson Tatum and Jaylen Brown.
The Risk:
The Celtics did pay a hefty price. Robert Williams III is a defensive anchor when healthy, and they gave up two valuable first-round picks. But in an all-in year, it’s a calculated risk worth taking.
Portland Trail Blazers Grade: B-
Why It’s Complicated:
The Trail Blazers are clearly rebuilding, and flipping Holiday for long-term assets makes sense. They now have a treasure trove of first-round picks and a young core centered around Scoot Henderson, Shaedon Sharpe, and Anfernee Simons. However, the logic gets murkier when analyzing fit and development.
The Good:
- Draft Capital: Portland now owns multiple future firsts, including a high-upside 2029 Boston pick.
- Robert Williams III: If he stays healthy, he could be a perfect rim-protecting complement to Portland’s guard-heavy core.
- Flexibility: This deal gives GM Joe Cronin room to maneuver with young players and trade chips.
The Questions:
- Anfernee Simons’ Role: With Scoot Henderson likely running point and Sharpe rising fast, where does Simons fit? He’s a high-volume scorer but needs the ball to thrive. Could he be the next to be traded?
- Crowded Backcourt: Simons, Sharpe, Scoot, and now Brogdon—who reportedly isn’t thrilled about his role—makes for a crowded rotation. Developing chemistry and defining roles will be a major challenge.
- Injury Concerns: Williams is an injury risk, and Brogdon has his own medical history. The Blazers’ return could end up limited if both struggle to stay on the court.
Final Verdict
This trade solidifies the Celtics as top-tier title contenders by adding a championship-tested veteran who fits their culture and needs. The Blazers, meanwhile, continue their rebuild, prioritizing draft picks and player development. Whether they’ve acquired the right pieces remains to be seen, especially as they sort out the Anfernee Simons conundrum and the ripple effects across a young roster.
Trade Grades Summary
- Celtics: A
A win-now move that makes them favorites in the East, balancing defense and experience. - Trail Blazers: B-
A solid return in terms of assets, but questions linger about fit, player roles, and long-term vision.
What’s Next?
Expect Portland to remain active, possibly fielding calls on Simons or Brogdon. As for Boston, it’s championship or bust—and they just got a lot closer to “championship.”
