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Celtics could run into Anfernee Simons realization Blazers know all over again

If the Boston Celtics target Anfernee Simons in free agency, they could run into the same offense vs. defense realizations they and the Portland Trail Blazers know all over again.
Dec 30, 2025; Salt Lake City, Utah, USA; Boston Celtics guard Anfernee Simons (4) brings the ball up the court against the Utah Jazz during the first half at Delta Center. Mandatory Credit: Rob Gray-Imagn Images
Dec 30, 2025; Salt Lake City, Utah, USA; Boston Celtics guard Anfernee Simons (4) brings the ball up the court against the Utah Jazz during the first half at Delta Center. Mandatory Credit: Rob Gray-Imagn Images | Rob Gray-Imagn Images

The Boston Celtics have some work to do this summer, and some outlets are suggesting that they rekindle things with Anfernee Simons, whom they traded at this year’s deadline. But that could just result in them realizing the same old realization the Portland Trail Blazers all over again: Simons is a valuable scorer, but his defense is still a lot to overcome.

Simons could have helped the Celtics solve some of their scoring woes in this year’s playoff run, but at the same time, they would have had to deal with his bad defense against a Philadelphia 76ers lineup that was tearing them to shreds. If they re-sign Simons this summer, they are bound to fall into the same situation.

Portland knows it well, and it’s part of the reason the Blazers traded Simons in the first place.

Blazers already know the deal with Anfernee Simons, but the Celtics could learn it all over again

When he’s on, he’s on. Simons can be one of the best scorers on an NBA court at any given time. That’s the value he brings to the table, and perhaps it’s a value the Celtics want back.

They traded Simons for Nikola Vucevic at this year’s deadline, largely for tax reasons. And to be honest, the Celtics missed his scoring at times. When they went through a drought, people were quick to want Simons back.

And perhaps he could actually help them next year. His shot creation and three-point shooting would be a nice addition to the lineup if the Celtics can round things out.

But the defense is, and always will be, an issue. Simons improved as a defender in Boston, but he was still always a consistent weak point that they had to work around.

If the Celtics sign Simons without knowing that as a certainty, then they could end up in the same predicament the Blazers ran into by the end of his tenure in Portland came around.

The Blazers could have re-signed Simons. They could have handed him an extension. But they knew the limitations that came with having him on the roster.

So, they traded him for Jrue Holiday. Boston got to shed some money, and the Blazers got a great veteran to help them on and off the court. 

Now, if the Celtics actually do end up targeting Simons in free agency, the defensive conversations could spark up again, and they will have to weigh his offensive value versus those potential problems.

It’s a problem the Blazers and Celtics both know by now, but Boston could still choose to walk down the same path they’ve already treaded.

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