Shaedon Sharpe's rookie-scale extension is one of the Portland Trail Blazers' most significant decisions this offseason. Of course, they'd like to keep their former No. 7 overall pick around long term as a foundational piece in their rebuild. He's just 21 years old and arguably still their best bet at having an All-Star currently on the roster due to his athleticism, positional size, and expanding offensive skillset. But the question lies more in how much they would feel comfortable paying him and whether they'd be better off letting him become a restricted free agent in 2026.
Sharpe's offensive impact is undeniable. He's averaging 17.5 points per game and is already great at attacking downhill, as well as getting to his spots in the midrange. The 31.8 three-point percentage is slightly concerning and something he'll have to improve to take that next step as a go-to player for Portland. But there are very few concerns surrounding whether he'll figure it out on the offensive end to justify a massive deal.
The problem with Sharpe and hesitancy in investing so heavily into him comes on the other side of the ball.
Sharpe's defensive struggles put Blazers in tough spot ahead of rookie extension
Sharpe has a 118.5 defensive rating, the second worst of the Blazers' core players behind Anfernee Simons (119.7). Too often, he has defensive breakdowns, whether from his fundamentals, awareness, or tendency to expend more energy on the offensive end. As an elite athlete with positional size at 6-foot-5, Sharpe has the physical tools to become a solid defender. But he hasn't yet been able to translate those tools into a two-way player who impacts winning at a high level as much as the Blazers have hoped.
Chauncey Billups' decision to bench Sharpe midseason because of his defense was polarizing. On the one hand, it doesn't make sense for the Blazers not to have their potential-packed backcourt as a priority this season, especially when their goal is player development, and they have no realistic playoff aspirations. But you also can't blame Billups -- who is potentially auditioning for a new coaching job -- for making what turned out to be the best decision for the Blazers from a win-loss standpoint.
Still, the fact that Billups' best decision to help the Blazers win more games lies in the benching of the player they need to make such a crucial decision on this summer is unfortunate timing. Portland finally has a larger sample size surrounding Sharpe, who was limited to just 32 games last year due to a core muscle injury. But there are still more questions than answers as he finishes his third season.
The Blazers face a similar predicament with Simons. His contract is set to expire after next season, and although he's a prolific scorer, is he worth being one of the Blazers' highest-paid players if he is a defensive liability? It still seems much easier to keep Sharpe around long term rather than Simons for several reasons, including age, upside, and Scoot Henderson's ascension.
Betting on players with untapped potential is something that many up-and-coming teams have to do. Recently, it was Trey Murphy III, Jalen Suggs, and Jalen Johnson. Those deals in the $25-30 million range have worked out great for their respective teams. However, investing in these players seemed safer because their impact as two-way players gave them a higher floor.
We know Sharpe will likely be atop Portland's leading scorers for the next decade if he sticks around that long. But the Blazers already have enough one-dimensional players like Simons, Jerami Grant, and Deandre Ayton, who are great scorers but don't impact winning in other aspects as much as you'd like.
The Blazers' young core of Henderson, Sharpe, Deni Avdija, Toumani Camara, and Donovan Clingan are finally addressing problems that Portland's roster previously had as a team that lacked defense, size, and physicality. But as we wrote about with Simons, a team's defense can only be as good as its weakest link. If Sharpe can't show drastic improvement on the defensive end, the Blazers should be more hesitant to lock themselves into something that could potentially set back their rebuild.
Portland only has 15 games remaining to evaluate Sharpe's defense before making a potentially franchise-altering decision this summer. He's just 21 and has plenty of time to develop into a two-way player before the Blazers need him for a deep playoff run. But if Sharpe's defensive struggles continue for the remainder of the season, the Blazers will be forced to weigh the risk of committing to a massive deal.