The Portland Trail Blazers are heading into the season with a backcourt situation that looks increasingly hard to ignore, and Scoot Henderson and Shaedon Sharpe are right in the middle of it.
Bleacher Report’s Dan Favale recently put both young guards on a list of players he thinks are most likely to end up in the 2026-27 trade rumor mill. His view was blunt: "At this point, the real shock will be if both Henderson and Sharpe finish next season on Portland's roster."
The only other team with two players on that list was New Orleans, where the same kind of roster confusion seems to be hanging over the franchise. Favale didn’t soften that point either: "Related: If anybody knows what in the hell this [Blazers| team is doing, please let us know."
For Portland, the issue isn’t just that Henderson and Sharpe are talented young pieces. It’s that the Blazers don’t appear to be moving quickly to settle the backcourt pecking order.
They’re not buying out Jrue Holiday, and they’re entering the season with a crowded guard group that also includes Damian Lillard and Ja Morant. That setup has only made it tougher for Henderson and Sharpe to claim a clear long-term lane.
Last season looked like a chance for one of the two former top-10 picks to take control. Instead, Henderson was slowed by an offseason hamstring injury and never really settled back into the offensive structure once he returned. His play was uneven from there.
Sharpe, meanwhile, posted the best statistical season of his young career. Even so, Portland still hasn’t figured out how to turn that production into more wins. Tiago Splitter couldn’t even count on him for a steady role in the playoff series against the Spurs, where Sharpe played only 13.4 minutes per game.
There’s also the contract side of the equation. Henderson is eligible for a rookie-scale extension right now, while Portland already locked up Sharpe on a four-year, $90 million extension last summer.
On paper, Henderson might seem like the obvious candidate to move because Portland has so many point guards. But Favale’s read points the other way, at least in terms of comfort level.
Henderson’s work ethic, compared with Sharpe’s, could make the Blazers more willing to keep betting on him. He’s also developed more into a 3-and-D guard, which gives him a cleaner path to fitting alongside others in an off-ball role.
The simplest move might be for Portland to wait and see. Starting the season without forcing anything would give the Blazers until the February trade deadline to figure out who fits and who doesn’t. Still, Favale’s larger point stands: it would be surprising if at least one of Henderson or Sharpe doesn’t come up in trade conversations this season, and maybe even more than that.
For a rebuild, it’s a jarring place to be. But after years of uneven play, it’s also the kind of decision point that eventually had to arrive.
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That uncertainty matters because Henderson is extension-eligible this offseason, and the Blazers may have to sort out his future sooner than they planned. If Portland decides it can no longer treat him as a centerpiece, there are already teams watching for an opening, with Boston, Detroit and Charlotte all profiling as possible landing spots for a young two-way guard who still has value around the league. [Read more 🡒]
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