The Portland Trail Blazers unofficially traded Anfernee Simons to the Boston Celtics on June 23. Simons has yet to play a game with his new team, but it already looks like the Blazers were wise to move on.
The Celtics mainly traded for Simons to get under the second apron. They don't actually want him. That's become clear as Boston has already made Simons available for trade. The issue, however, is that no other team seems to want Simons either, meaning the Celtics are likely stuck with the combo guard to begin the 2025-26 season.
Celtics struggling to flip Simons proves Blazers made the right call
Simons is an extremely gifted player. He's a consistent 20-point scorer, a reliable three-point threat, and an underrated playmaker who had the best assist-to-turnover ratio on Portland's roster last season. But he doesn't come without his flaws.
Simons is one of the worst perimeter defenders in the entire league. His combo guard skillset also presents teams with a roster dilemma -- he's not a traditional lead guard, but is too undersized to play alongside another point guard. There are exceptions, such as if he were to play alongside a jumbo guard like Cade Cunningham in Detroit. Still, these concerns are compounded by the fact that Simons is on an expiring contract.
Portland made the right decision to move on from Simons because they would never become an elite defense with him in the equation. That said, general manager Joe Cronin didn't get the timing of the trade right, which has been a theme throughout the Blazers' rebuild. Simons' next contract wouldn't have been as much of an issue if it were a few years away. Now, it's too close for teams to be willing to invest twice in the skilled but flawed guard -- once when they initially give up assets to acquire him, and again when they commit to a long-term deal.
Portland was fortunate to find the right trade partner for a Boston team that desperately needed to shed salary, especially after Jayson Tatum's brutal Achilles injury. But now, the Celtics aren't having the same luck finding another desperate team to take on Simons and his looming extension decision.
Say what you will about whether Jrue Holiday was the right piece to add to an up-and-coming Blazers roster -- he's certainly an expensive mentor at 35 years old. But that deal doesn't look as bad knowing that the alternative was Portland paying Simons in the same ballpark to retain him. And we all know who is the more impactful player between the two.
The fact that Boston is struggling to flip Simons proves that Portland was right to move on while they still could.