Anfernee Simons has gone on record saying he "wants the opportunity to win". Now entering his eighth season in the NBA, he'll finally get that chance to play for a contender. The Portland Trail Blazers have shipped their prolific guard to the Boston Celtics, along with two second-round picks, in exchange for Jrue Holiday.
Before the trade, Simons was the Blazers' longest-tenured player. He was also the final piece remaining from the Neil Olshey era. It's surprising in the sense that Portland landed a 35-year-old guard. But the writing has been on the wall for Simons to leave Rip City for quite some time.
It was only a matter of time until Anfernee Simons was gone
It was clear that the rebuilding Blazers needed to prioritize former No. 3 overall pick Scoot Henderson, and this trade still accomplishes that in a roundabout way. But there were even signs from what Simons and general manager Joe Cronin have said in the past.
On draft night in 2024, Cronin subtly hinted at a future Simons trade when he said the Blazers were committed to building around Scoot Henderson and Shaedon Sharpe without mentioning Simons' name.
While Simons never formally requested a trade, he also appeared open to it. In his end-of-season exit interview last year, Simons said, "We don't want to have another year like this. My sixth year is done now, and going into year seven, I want to have the opportunity to win."
While Portland did have a 15-win improvement, it still resulted in a 36-46 record, which likely wasn't what Simons meant by having the opportunity to win.
Then there was Jason Quick of The Athletic's article in January, which revealed things weren't going well for Simons. At the time, Portland had an 11-22 record, which was taking a toll on Simons. At the end of the season, he called it "the toughest one [he's] had, just mentally."
Why Boston is a perfect fit for Simons
It wasn't just the losing, either. There have been a ton of moving parts that took a toll on Simons, who has endured a lot of highs and lows in his seven seasons in Portland. One of which was the change in the Blazers' style of play as Chauncey Billups began to emphasize a more transition-oriented style of attack.
"Once you've been used to playing kind of a half-court offense your first six years in the league, it's kind of hard to adjust," Simons said. "Because that's how I learned the NBA game was through running sets. So, that was pretty hard for me. But I feel like I figured it out kind of midway through the season."
This trade is a perfect fit for both teams regarding the style of play. The Blazers add one of the best perimeter defenders in the league in Holiday. Given his age, declining play, and contract, it's fair to question whether it's in Portland's best interest to actually acquire Holiday. But one thing you can't dispute is that he's an ideal addition to the identity Cronin and Billups have been establishing over the past few seasons as a hard-nosed, defensive-minded team.
Meanwhile, the flamethrower Simons heads to Boston, who led the league in three-point attempts this season. They also already have the defensive pieces to compensate for his weaknesses. It may be difficult to contend next year without Jayson Tatum and Kristaps Porzingis, who is suddenly heading to Atlanta. Still, this trade is a significant upgrade for Simons. He finally gets to play winning basketball and, even better, on a team that fits him perfectly.