Celtics fans will love the 'stigma' Anfernee Simons is eager to earn

Anfernee Simons wants to use his newfound spotlight to prove he is a winning player.
Sep 29, 2025; Boston, MA, USA; Boston Celtics guard Anfernee Simons (4) talks with reporters during media day at the Auerbach Center. Mandatory Credit: David Butler II-Imagn Images
Sep 29, 2025; Boston, MA, USA; Boston Celtics guard Anfernee Simons (4) talks with reporters during media day at the Auerbach Center. Mandatory Credit: David Butler II-Imagn Images | David Butler II-Imagn Images

Anfernee Simons spent the first seven years of his career with the Portland Trail Blazers. He hasn't participated in the second round of the playoffs since his rookie campaign. Even then, he only appeared at the end of the series opener after his team emptied the bench.

Portland missed the postseason the last four years. Conversely, the Boston Celtics have made trips to the Eastern Conference Finals feel like an annual tradition. The franchise could be in store for a gap year. They're dealing with the consequences of spending the last two campaigns over the second apron. The need to gain flexibility coincides with Jayson Tatum's rehabbing a torn Achilles tendon.

However, as Simons suits up in a major market for a team prominently showcased, he is eager to exchange his current reputation for a new one.

"That I can impact winning," the seven-year veteran told Hardwood Houdini after day two of training camp at the Auerbach Center. "I think that was one of the big things that you could say about me, is that in the last couple [of] years, where I've been the main guy, we didn't win. So, I want to come in -- like I said before -- no matter how it looks like, I want to have that winning player stigma on me, and so that's pretty much simple.

"No matter what it looks like, how hard it is, how much of an adjustment it can be, ups and downs, I want to be able to stretch myself into being that type of player."

Anfernee Simons has a golden opportunity

The 26-year-old guard is entering a contract season. It's an ideal time for him to join a winning organization and earn his desired reputation. He is also an excellent fit in the offensive system he is about to start operating in.

Simons is a dynamic three-point shooter. He's potent off the dribble and off the catch, and he remains that way at a high volume. He has also spent the last few years gaining valuable experience as Portland's primary offensive option. At media day, he expressed his excitement about working alongside individuals such as Jaylen Brown, Derrick White, and Payton Pritchard. Both sides will make life easier for each other.

That includes Simons being an underrated facilitator. He is averaging 4.5 assists over the last four years. If he answers the Celtics' challenge to him defensively, one he is eager to meet, perhaps he'll extend his tenure in Boston.

Given his foot speed and six-foot-seven wingspan, he has the tools to do so. Producing 1.2 deflections per tilt last season is a testament to the impact he can make with his length on and off the ball.

Meeting that challenge of becoming a more effective two-way player is Simons' ticket to proving to the basketball world that he's a winning player. It could also convince his new team that he's too valuable to see walk out the door.