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Celtics could help solve Trail Blazers' tricky logjam at guard

The Trail Blazers' current roster makeup is bizarre to say the least...
Apr 10, 2026; Portland, Oregon, USA;  Portland Trail Blazers guard Damian Lillard (0) watches his teammates during warm ups before the Trail Blazers play against the LA Clippers at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images
Apr 10, 2026; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) watches his teammates during warm ups before the Trail Blazers play against the LA Clippers at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images | IMAGN IMAGES via Reuters Connect

The Boston Celtics have made moves that have certainly confused the masses this offseason, but at least there's a rationale behind them: they didn't believe a core featuring Jayson Tatum and Jaylen Brown could win anything substantial going forward. We'll see whether they're right, but at least we understood why. The Portland Trail Blazers are a different story with the moves they've made.

They were a suitor for Jaylen Brown until they traded for Ja Morant. In all fairness, acquiring Morant cost them nothing, compared to Brown, who may have been sold for less than what everyone thought he was worth, but at least the Celtics got something back for him. Regardless, though, the Trail Blazers' guard rotation is just odd.

Morant joins a guard rotation that features old friend Jrue Holiday, Scoot Henderson, Shaedon Sharpe, and of course, the return of Damian Lillard. While having a bunch of talented guard in one rotation isn't a bad thing, all of them will demand time and touches.

Maybe Portland plans to go ultra small this season, but it's hard to see the vision for how this works. Getting Morant may have also signaled a lack of confidence in either Henderson's development or Lillard returning to form (makes sense given his age and coming off a torn Achilles).

They haven't made any moves since, thus likely signaling they will roll with this crew, but there's a solid chance this will not work, and if it doesn't, Boston could help bail them out.

Boston could use Anfernee Simons TPE to take Trail Blazers guard

For the record, because the Celtics are hard-capped at the first tax apron, they can't just absorb anyone paid $27.7 million or less from the Anfernee Simons trade exception, but they can still use it as long as they stay below the first tax apron.

Right now, they are $10 million below it, give or take. If Portland decides their guard rotation isn't cutting it (hot take: it won't take long for them to make this realization), Boston could swoop in and take one of their guard, specifically either Dame (he might not be what he was but could easily transition as a backup) or Henderson (young talent who showed progress in the playoffs).

Boston has a solid guard rotation with Derrick White and Payton Pritchard while also adding some depth with Mike Conley Jr., but at Conley's age, there's no telling how much he has left in the tank. Another guard could be just what the doctor ordered in case Conley isn't enough.

Having one of Lillard or Henderson could plug that hole easily and then some. Neither Boston nor Portland has to worry about this, but if it becomes a concern, they could easily become trade partners in the not too distant future.

Of course, we thought the same thing about Jaylen Brown last month...

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