The Portland Trail Blazers roster is unfinished heading into 2026-27. It's like general manager Joe Cronin ran out of time on a test, filled out the rest of the Scantron with all As, and hoped some answers would be right. In this case, the As are the point guard position. An area once thought to be a strength for Portland, which had the luxury of going from Damian Lillard to No. 3 overall pick Scoot Henderson.
Their rebuild has taken unexpected twists, as picks like Henderson haven't quite panned out as expected. Fortunately, Cronin has kept the rebuild on track through impressive trades, landing building blocks Deni Avdija and Toumani Camara. Their versatile wing duo, paired with defensive anchor Donovan Clingan, proved to be the true building blocks of this rebuild.
Now comes the hard part as Cronin enters the next phase of this rebuild: making the pieces fit. While it's easy to see the value in scalable two-way role players like Sidy Cissoko and Henderson, others with defensive or floor-spacing problems will be much harder to justify continued investment in.
Develop: Sidy Cissoko
Cissoko surprisingly played a key role for the injury-riddled Blazers last season, even starting in 26 games despite initially coming on as a two-way signing. Portland converted Cissoko's contract to a standard one, showing their willingness to continue investing in his growth.
He should continue to play a role for Portland this season with forwards like Jerami Grant, Kris Murray, and Matisse Thybulle out of the picture. While the three-point shot remains a concern, he's at least trending upwards offensively at 22 years old. Given their lack of wing depth and the market value of two-way wings around the league, Cissoko is an obvious piece to keep around for now.
Move on from: Shaedon Sharpe
In a sense, the Blazers already committed to Shaedon Sharpe's development when they reached a four-year, $90 million extension before the start of last season. But the NBA landscape is rapidly evolving. A surprising Ja Morant trade, followed by another Sharpe injury, suddenly makes Portland's high flyer the odd one out in this new-look backcourt.
It's a risky proposition to move on from Sharpe given his star ceiling if he's ever able to become a more consistent and complete player, figuring out how to utilize those elite physical tools to become more of a two-way guard.
But with Sharpe now an afterthought on the depth chart, it increasingly looks like a breakout would have to come where he is more of a focal point. It could eventually be in both parties' best interest to move on: Portland adds more shooting and defense, and Sharpe becomes a go-to option elsewhere.
Develop: Scoot Henderson
The Blazers may have extended Sharpe, but this offseason they still face a dilemma regarding what to do with their first-round selection the following year. Henderson is eligible for a rookie-scale extension, which becomes increasingly unlikely the closer we get to the season.
The extensions reached by Henderson's 2023 classmates (Keyonte George, the Thompson Twins, etc.) do make this pick sting a bit more lately. While teams are comfortable committing to the building block they landed in that year's draft, Portland still doesn't know whether Henderson is worth it.
Part of that comes from the limited evaluation they've been able to do, as Henderson was sidelined with an untimely hamstring injury during an offseason workout last season. It was largely viewed to be a make-or-break season for Henderson, who now has an uphill battle to climb out of this messy Blazers point guard depth.
But to his credit, Henderson has quietly done an impressive job of re-energizing himself as a two-way guard. Work ethic has always been a standout trait of Henderson's, and you can already see that progress in his development as a 3-and-D guard. It also shouldn't come as a surprise that Henderson had a career year defensively in his first season with Jrue Holiday as his veteran on-court mentor.
Whether the Blazers extend Henderson soon or let him hit restricted free agency next summer, they need to retain him. Say what you will about how he's been relative to draft expectations, but that narrative has also made Henderson underrated in the newfound role he's carved out for himself in the Pacific Northwest.
Move on from: Jeremy Sochan
The Blazers bought in on Jeremy Sochan on a non-guaranteed deal. They decided it was worth a closer look at a former top-ten pick, giving Sochan an opportunity to compete for a spot on the 15-man roster against former Indiana Pacers big man Micah Potter.
The Blazers claimed Potter after he was waived by Indiana, meaning they took on his non-guaranteed contract in the process. Now it appears they are taking a similar training camp approach as the New York Knicks, bringing in multiple players to compete for the remaining roster spots.
It doesn't hurt to add competition for Potter. That is, as long as Portland recognizes he's the far better fit for this roster than Sochan. The contrasting playstyles between the defensive-minded Sochan and the floor-spacing Potter are almost as obvious as which one the Blazers roster needs more of.
The idea of Sochan is far better than the actual thing, and it's much easier to see Potter carve out a valuable role off the bench as a stretch big man. They already have enough floor-spacing concerns and need to address that problem on the margins by ultimately moving on from the Sochan experiment.
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