"We don't want to have another year like this. My sixth year is done now, going into year seven, I want to have the opportunity to win." That's what Anfernee Simons said at his exit interview after the Portland Trail Blazers' 21-win season in 2024.
Then, in January 2025, Jason Quick of The Athletic published a piece noting that Simons is going through the "hardest mental battle" he's endured in his career, with Portland's losing situation being a key contributor in that.
"Obviously, not winning as much as you would like the last couple of years, it can get on you mentally," Simons said.
At the time of that writing, the Blazers had an 11-22 record, which was sixth-worst in the NBA. They managed to turn things around towards the end of the season, finishing 36-46, tied with the Phoenix Suns for the ninth-worst record. Although Portland's young core is showing signs of progress with a 15-win improvement, it's hard to imagine this is what Simons had in mind when he said he wanted the "opportunity to win."
He'll finally get that, and more overall organizational stability, with the Boston Celtics.
Blazers sent Anfernee Simons to a winning situation
The Blazers swapped offense for defense in the Simons-Jrue Holiday trade. Holiday is the more impactful player, but Boston wanted to duck the second apron, potentially making this a rare win-win deal.
It was uncertain whether the Celtics would proceed to flip Simons to better balance their roster, especially after all their frontcourt departures this offseason. However, teams appear to be reluctant to sacrifice valuable assets to acquire Simons, knowing that he's on an expiring deal; that makes it likely that Simons will remain in Beantown for the time being.
Even considering Jayson Tatum's brutal Achilles injury, Simons will still have a golden opportunity to win in Boston. Brad Stevens' moves may suggest that they are viewing this as a gap year with Holiday and Kristaps Porzingis out of the picture. But the reality is the Eastern Conference is wide open for the taking. The Cleveland Cavaliers and New York Knicks should be considered the favorites to represent the East, with the Orlando Magic emerging as a dark horse after the Desmond Bane deal. Still, each team has its respective roster construction flaws, giving Boston a realistic shot.
There's also the possibility that the Celtics do retain Simons long-term, especially if he's able to embrace a sixth man role as a combo guard to spell both Payton Pritchard and Derrick White. Offensively, Simons is a perfect fit for Celtics head coach Joe Mazzulla, as Boston attempted the most three-pointers in the league last season.
The situation surrounding Simons' expiring deal and the uncertainty of whether or not he'll remain in Boston long-term isn't ideal. But he was inevitably going to have to address that regardless of his landing spot. For the time being, he remains in Boston. And from a pure winning standpoint, few organizations do it better.
By shipping him to the Celtics, Portland finally granted Simons his wish.