The Portland Trail Blazers have until the start of the 2025-26 regular season to extend former top-ten pick Shaedon Sharpe. If not, he will enter restricted free agency next offseason. These extension talks are tricky for any general manager to navigate, but especially for Joe Cronin, given Sharpe's situation.
Portland should keep Sharpe around for the long haul because of his star upside. They would be kicking themselves if he reaches his ceiling and becomes one of the best two guards in the league while wearing another team's jersey. But how much is he worth? Should they extend him or let the RFA market determine that value? That could depend on how they view his role on the Blazers' roster.
How should Portland navigate Shaedon Sharpe's extension dilemma?
On the one hand, Sharpe is coming off a promising third season in which he averaged a career-high 18.5 points along with 4.5 rebounds and 2.8 assists. On the other hand, he shot a career-low 31.1% from beyond the arc and was a massive defensive liability. Sharpe had the second-worst defensive rating (117.2) among qualified players on Portland's roster. With Anfernee Simons now out of the picture, Sharpe has suddenly become the worst defender on their team.
It's puzzling because he has the physical tools to be an impactful defender given his positional size at 6-foot-5 and elite athleticism, but that also highlights the general problem surrounding Sharpe -- the theoretical version of him as a player is way different than the reality as he's yet to put it all together.
Some may find it concerning for Portland to invest in him long-term, especially because of Sharpe's nonchalant style of play, which leaves some to wonder if he's assertive enough to ever emerge as that go-to player. However, Sharpe's career trajectory is understandable considering he's just 22 years old and didn't even have a chance to develop by playing meaningful games at the collegiate level.
Sharpe was the top-ranked recruit in the 2022 class before graduating high school early and sitting out the entire 2021-22 season at Kentucky. The Blazers took a relative gamble on him with the No. 7 overall pick. That's already proven to be worthwhile, but the extent to which it has paid off remains unclear.
Portland already invested in Sharpe once as a player when they drafted him before knowing what he would become. They need to continue doing that with this next deal, likely paying him more than he's currently worth as they project him to continue that upwards trajectory. But what exactly is that number?
The upside is undeniable, but where Sharpe fits into the scheme of things is where things get murkier for Portland. After bringing in Jrue Holiday and Damian Lillard this summer, they now have several ball-handlers and scorers. Is Sharpe best utilized as a sixth man or a starter in this suddenly crowded backcourt? That answer will determine how much he is worth.