During his time with the Portland Trail Blazers, Anfernee Simons made it clear that all this losing was taking a toll on him. At his end-of-season exit interview following Portland's 21-win season in 2024, Simons said he wanted the "opportunity to win." While the Blazers won more games and even exceeded expectations the following year, a 36-win season isn't exactly what he meant. Simons wanted to play for a contender.
Although he still fit the Blazers' rebuild from an age standpoint, it was clear that his pressing desire to win no longer aligned with Portland's patient rebuilding timeline. Blazers general manager Joe Cronin also mentioned that the Blazers were "committed" to building around their recent top ten picks, Scoot Henderson and Shaedon Sharpe. Simons wasn't mentioned, leaving many to wonder whether he was part of their long-term plans.
With his contract set to expire after the 2025-26 season, this past summer presented an opportunity for Portland to finally move on from their talented combo guard. Fortunately for Simons, the Blazers sent him to one of the best organizations in the league: the Boston Celtics.
Celtics are giving Anfernee Simons the "opportunity to win"
It wasn't a smooth transition by any means. Boston almost immediately looked to flip Simons as the motivation behind the Jrue Holiday swap was primarily financial. But now, halfway through the season, Simons and the Celtics finally seem to be a good match for each other.
Some expected Boston to take a gap year with Jayson Tatum still recovering from an Achilles tear and Holiday, Kristaps Porzingis, and others out of the picture. Yet they surprisingly sit 2nd in the Eastern Conference behind only the Detroit Pistons.
Simons has suddenly become a key piece in that success, granting his own wish in a way. He recently almost single-handedly won Boston a game over the Miami Heat, with a season-high 39 points.
Both Simons and the Celtics are trending in the right direction, which could cause them to reevaluate their plans ahead of the Feb. 5 trade deadline. While Simons should still be considered a trade candidate, it wouldn't be surprising if the Celtics ultimately decide to hold onto him to help make a deep playoff run. The Eastern Conference is somehow even weaker than expected, giving Boston a legitimate shot at a path to the Finals if Tatum returns in time.
Things have to go right for Simons in the coming weeks, both in terms of not being traded and Tatum returning, which seem to go hand in hand, as Boston's stance as a buyer or seller will hint at whether they plan for their star wing to return in time.
Hopefully, for Simons sake, he's able to stick around, as he's finally getting everything he's wanted all those years in Portland.