Roughly two months have passed since the Portland Trail Blazers shocked the NBA world by trading Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday. Boston has already explored trade options for Simons, but it seems likely that they will head into the 2025-26 season with him still on their roster. Teams around the league are reluctant to sacrifice valuable assets to acquire Simons, primarily because of concerns surrounding his expiring contract.
Simons is a prolific offensive player, but doesn't quite impact winning as a two-way guard enough to justify a massive next contract, especially under the new CBA. It's ironic because Boston swapped Holiday for Simons to dodge the second apron, but now they are struggling to flip Simons for financial reasons.
If the Celtics do keep Simons around in Boston, there's a possibility that they will bring him off the bench in a sixth-man role, with Payton Pritchard and Derrick White starting in the backcourt. Blazers fans who have watched Simons throughout the first seven years of his NBA career know that this is his ideal role on a contender.
Celtics realize Anfernee Simons can't start on a contender
Simons is still just 26 years old and fits Portland's rebuilding timeline, but Blazers general manager Joe Cronin decided to move on from him to clear the backcourt for former top ten picks Scoot Henderson and Shaedon Sharpe. Those two guards have substantially higher ceilings than Simons, and Portland was right to finally prioritize them, both from a developmental and evaluation standpoint.
Simons had the worst defensive rating on Portland's roster last season, which didn't align with the roster identity Cronin has emphasized. He could've still had value in a sixth man role due to his combo guard skillset, but again, that brings up the question of maximizing their roster. Simons was already one of Portland's highest-paid players at $27.7 million, and could command more than that annually in his next deal, just entering his prime. The Blazers' ceiling would've been significantly limited if Simons had remained one of their highest-paid players.
He had several productive seasons in Portland, averaging 15.0 points, 3.3 assists, and 2.5 rebounds on 43/38/88 shooting splits so far in his career. But it's a catch-22 situation: Simons is best served in a sixth man role on a contender, but teams can't build a contender around the contract he demands.
Boston will have to continue retooling their roster, and should ultimately come to the same conclusion as Portland did. Considering that the Celtics have explored trade options and are now considering bringing him off the bench, it's clear they are already questioning how Simons fits into their roster -- if he does at all.
It's the same dilemma the Blazers faced, and they ultimately came to the correct conclusion by sending Simons elsewhere while they still could.