Anfernee Simons has made it clear that he wants to play on a contending team. At the end of the 2023-24 season, Simons said, "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."
The Portland Trail Blazers exceeded expectations last season with a 15-win improvement and an exciting end-of-season chase for a play-in spot. Still, a 36-win season doesn't exactly align with Simons' wish to win. He'll finally get that opportunity with the Boston Celtics, who are just one season removed from winning the title.
Celtics' trade struggles make Anfernee Simons' wish come true
Better yet, it's increasingly likely that Simons will remain in Boston -- at least for now. NBA insider Jake Fischer noted that the Celtics were open to flipping Simons after acquiring him from Portland, but are having difficulty finding a trade partner offering any significant value. A primary reason why the Blazers moved Simons in the first place was his expiring contract. He's a great player, but not worth the amount it will cost to retain him long-term relative to his two-way impact on winning. Other teams around the league know that, too.
These may not be the exact circumstances Simons envisioned when he said he wants to play for a contender. Yes, he'll finally get that opportunity in Boston. But he's also playing for a team that clearly is keeping him around because they have to, not because they want to. Additionally, there's a chance that Celtics head coach Joe Mazzulla could bring Simons off the bench, starting Sixth Man of the Year Payton Pritchard instead.
That's the harsh reality of Simons' situation. He's a skilled 20-point scorer and an underrated playmaker, but his combo guard skillset and defensive liabilities make him better suited as a sixth man if he genuinely does want to play on a contender. Teams' ceilings are significantly limited if he's one of the best -- and highest-paid -- players on the roster. He can be the face of a lottery-bound team like he was with Portland, or he can be a sparkplug role piece for a contender.
But even if Simons is willing to buy into this diminished role to chase his first ring, Jayson Tatum's injury is still an issue.
The Celtics players themselves aren't buying the idea that 2025-26 is a gap year, but the front office clearly is. Tatum is expected to miss an extended period of the season, and decision-maker Brad Stevens has dumped Jrue Holiday and Kristaps Porzingis to duck the second apron. They could still manage to make a playoff run due to being in the lackluster Eastern Conference, but this is no longer the same Celtics team that won it all in 2024.
That brings up the question: Will Simons still be around in Boston to see the peak of this retooling roster? Or is he merely someone they had to acquire for financial purposes but don't envision being part of the plans -- a stepping stone to help reach that peak? After seven tumultuous seasons with the Blazers, Simons deserves for it to be the former.