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Which 3 Guards Should the Trail Blazers Keep?

Portland has a quintet of decent backcourt players. How do they narrow down?

NBA: Portland Trail Blazers at Cleveland Cavaliers David Richard-USA TODAY Sports

The 2023-24 Portland Trail Blazers are long on potential, occasionally short on performance. Even though the pieces aren’t in place for success yet, the Blazers have some nice components. One reader wants to know how many they can, or should, keep going forward. That’s the subject of today’s Blazer’s Edge Mailbag.


The Blazers have five guards playing regularly now except when they’re injured. Can they sustain that many? If not, who should they keep as they move forward past the current rebuild?

Bryan H

It’s a great question, if nothing else because the issue is liquid.

If you’re looking at players most valuable to the Blazers right now, there’s zero doubt that Anfernee Simons and Malcolm Brogdon lead the list of guards.

The entire team calms down when Brogdon gets consistent court time. He’s the most capable point guard on the roster, with an impeccable and deadly sense of timing for his own scoring and shot selection. His vision is unmatched in this current group. I’ve described him as a one-man exhale for the offense. Everything looks, and runs, better when Brogdon is on.

Anfernee Simons does the same thing for Portland’s scoring (as opposed to playmaking). He can hit at all three levels. He’s a quick scorer. He gets on unstoppable runs that nobody else comes close to. In fact, we can double-dip this Mailbag with the following question:


Without Dame on the team, who will be the next Trail Blazer all-star?


The answer right now is Simons, and it’s not even close. Other players have the potential: Jerami Grant immediately, other guards down the line. But nobody shines or produces the way Ant does.

That makes the 2023-24 answer to the initial question easy: Simons and Brogdon, plus pick your favorite other guard among the rest. If you want to field the best lineup possible, those two are at the heart.

But those two aren’t my long-term answer. If we’re looking down the road, I’d invert the guard set precisely. I want to keep three backcourt players off of this team: Shaedon Sharpe, Scoot Henderson, and Matisse Thybulle.

Age is one factor. All are young. Simons is too, but by the time the Blazers get good, Brogdon will be ancient or out of the league. He’s not on Portland’s timetable, even though he’s uniquely qualified to captain them now.

Despite his amazing offensive abilities, Simons does not have the defensive chops that Sharpe, Henderson, and Thybulle display. He’s a better player overall than Thybulle for sure, and normally would be retained over Matisse. But I’m looking at continuity, consistency, salary, and fit.

Thybulle is going to work off the bench with any lineup. I don’t believe a three-guard starting corps of Scoot, Shaedon, and Ant will prosper long-term. Nor do I believe any can come off the bench. One of them has to go. Even though he’s the most valuable player for the Blazers right now, Simons is my candidate.

I believe that Sharpe can develop into a well-rounded offensive player. He won’t be the instinctive scorer that Simons is, but he’ll produce numbers. I also believe Henderson will develop enough of a three-point shot to stay viable. In last night’s game against the Sacramento Kings, I saw something from him I’ve not yet noticed all season: a soft release on his three-point shot. It was only one attempt and it missed, but the ball left his hand at least once like a true shooter, hitting the rim gracefully before bouncing across and out. It’s faint praise, but compared to his early three-point shot, it might as well have been a Rembrandt.

If Scoot and Shaedon fill out the offense, their main on-court liability will be resolved. Then we can concentrate on their overwhelming individual defensive potential and blooming synergy on that end. Simply put, they have the potential to be the best defensive backcourt in the league. They’re athletic, opportunistic, and both show a nose for “D”. Watching them close on shooters is a thing of beauty, and they can do it from a long ways away.

Throwing in Thybulle off the bench as a third guard keeps the defensive pressure high and the roster cost low. If small forward Toumani Camara ever develops a three-point shot, look out. Now the Blazers have two scorers and two shooters at their three smaller positions, all of whom have the potential to be masterful defenders. My toes are curling at the prospect.

That’s why, forecasting farther into the future than two years, I believe that Sharpe, Henderson, and Thybulle are the correct choices. Simons and Brogdon have earned the bulk of the playing time now, but that same excellence will make them valuable on the trade market when it’s time to clear the way for the next generation. Both have contracts in the mid-$20 million range, completely doable for players of their quality. A little return on those, some skillful drafting for the frontcourt, and the Blazers are in business.

How about you? If you were to keep 2-3 guards out of the current crop of five, which ones would you choose, long-term? Help answer Bryan’s question in the comment section below! And please don’t forget to help us send kids in need to see the Blazers play the Atlanta Hawks this March! Donating tickets is easy, and every one makes a difference! Click here to see how!

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