Anfernee Simons went on record as saying he wanted "the opportunity to win" heading into his seventh season with the Portland Trail Blazers. That never came to fruition, as Portland finished last season with a 36-46 record, falling short of the postseason for a fourth consecutive year. That was a promising improvement from the Blazers' 21-win season the year prior, but it still wasn't what Simons had in mind.
In January of the 2024-25 season, Simons told Jason Quick of The Athletic that he was going through "the hardest mental battle" he's had in his career, but still wouldn't request a trade. Simons had been a trade candidate for quite some time, as the Blazers seemed set on building their future backcourt around recent top-ten picks Scoot Henderson and Shaedon Sharpe. With his contract set to expire after this season, this past offseason presented an opportunity for Blazers general manager Joe Cronin to finally make that anticipated decision to trade him.
Cronin arguably should've traded Simons earlier to maximize his value on the market, but it's hard to argue with the results, as Jrue Holiday has started the season off on a strong note for Portland. Early on, Portland received the better end of this deal as Simons' time in Boston has been rocky.
Anfernee Simons still doesn't have the "opportunity to win"
The Celtics were financially motivated to acquire Simons in order to duck the second apron, but it remained to be seen if he would remain there. Boston had explored trade options but ultimately decided the value wasn't worth it, keeping Simons in a sixth-man role to start the season.
So far, he's averaging 14.3 points, 2.0 rebounds, and 1.6 assists on 41/38/83 shooting splits. Statistically, that would be Simons' worst season since 2020-21, his third year in the league. It's not entirely his fault, as he's averaging 26.9 minutes per game with a lower usage rate. However, this raises the question of how content Simons truly is in Boston.
He's taking on a lessened role on a team that has already tried to shop him. And perhaps most importantly, he's still not winning. The Celtics are 4-5 to start the season and don't appear to be contenders without Jayson Tatum, even in the weak Eastern Conference. In other words, it's not even a worthwhile sacrifice he's making!
To make matters worse, his former team is finally turning a corner as Portland is off to a 5-3 start. While we can't directly speak for Simons, this doesn't appear to be an ideal situation for him. He should be considered a trade candidate by February's deadline, with the Celtics potentially looking to get assets for him before his contract expires.
If they do trade him, hopefully the Celtics ship Simons to a genuine contender, giving him that opportunity to win he's always wanted.