Now that the Portland Trail Blazers roster is solidified heading into the 2025-26 season, general manager Joe Cronin must turn his attention to a potentially franchise-altering decision: what to do with Shaedon Sharpe's extension.
Sharpe is currently eligible for a rookie-scale extension and can negotiate with the Blazers until the start of the season. Sharpe will hit restricted free agency next summer if an extension doesn't materialize. It's a difficult decision with no definitive correct answer.
Pros of extending Shaedon Sharpe
Sharpe has arguably the highest ceiling on Portland's entire roster. He's coming off a season in which he averaged 18.5 points, 4.5 rebounds, and 2.8 assists, which is impressive for a 22-year-old. But there are just enough concerns surrounding whether Sharpe can take that next step and put it all together, lowering his value compared to what it could become next summer.
Sharpe shot just 31.1 percent from beyond the arc, had almost as many turnovers as assists, and is officially Portland's worst defender with Anfernee Simons now in Boston. Sharpe has top-tier athleticism and good positional size at 6-foot-5, which suggests he can eventually become a more complete player. If the Blazers are confident in that being the case, they could invest early.
Portland cleared the path for Sharpe to have a breakout season this offseason. Financially speaking, they may want to get ahead of that. He's someone they need to commit long-term to, whether that happens by October or next offseason. If the Blazers decide to commit now, they could get Sharpe at a discount.
Cons of extending Shaedon Sharpe
But what if Portland isn't confident in Sharpe putting it all together? Chauncey Billups didn't have enough confidence in Sharpe last season, benching him midseason because of his lackluster defense -- and Portland was better off because of it. They had a significantly improved defense, and as a result, their record improved following the benching.
Are we positive Portland doesn't have the next Jonathan Kuminga on its hands? That may be too extreme in Sharpe's case, but there are concerning similarities. Both players are uber-athletic former top ten picks that have good counting stats but don't impact winning enough at this point in their careers.
It's a tricky situation for Cronin to navigate. On the one hand, the Blazers' rebuild could be viewed as a waste if one of their recent top ten picks is no longer in the picture. On the other hand, Portland's true building blocks have changed from its backcourt to the frontcourt with their trades for Deni Avdija and Toumani Camara.
Ultimately, Portland needs to continue investing in Sharpe one way or another. He's young enough in his career to improve his shot and in those intangible areas outside of scoring. The Blazers roster desperately needs two things he offers: star upside and offensive creation.
But that investment should come next summer.
The Blazers are one of ten teams ESPN projects to have significant cap space in the 2026 offseason. They would be wise to hold off on any extensions to preserve that, setting themselves up for next summer, where they can make a splash and position themselves to return to the playoffs in 2026-27.