Blazers Have Key Decision to Make on Young Star Before Start of Season

Nov 10, 2024; Portland, Oregon, USA: Portland Trail Blazers guard Shaedon Sharpe (17) shoots the ball over Memphis Grizzlies guard Scotty Pippen Jr. (1) as Trail Blazers’ forward Toumani Camara (33) watches in the second half at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images | Jaime Valdez-Imagn Images

The Portland Trail Blazers have a critical decision to make on a young star ahead of the start of the 2025-26 season.

Portland has had a bit of a head-scratching summer.

The Trail Blazers traded away score-first combo guard Anfernee Simons, who's on an expiring $27.7 million contract, to the Boston Celtics in exchange for the pricier, older Jrue Holiday.

Holiday, a two-time All-Star and six-time All-Defensive Teamer, will shore up Portland's backcourt defense, yes. But he also clogs up the club's backcourt rotation, as he'll likely cut into the minutes of young former lottery pick guards Shaedon Sharpe and Scoot Henderson.

But the 6-foot-4 UCLA product is also nine years Simons' senior, and Portland's physical of Holiday revealed some healthy issues that compelled the Trail Blazers front office to not include the two second-round draft picks that were initially being sent out to the Celtics as part of the deal. The 35-year-old is owed across the next three years.

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Trail Blazers general manager Joe Cronin, who along with head coach Chauncey Billups was extended after a solid finish to their 2024-26 season, opted to buy starting center Deandre Ayton out of the final year of his deal, as well. He signed with the Los Angeles Lakers on the heels of a 50-win season, and will now supplant freshly-demoted big man Jaxson Hayes.

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Cronin also traded out of the lottery to select young former CBA center Yang Hansen with the No. 16 pick in the 2025 NBA Draft. Hansen appears poised to serve as the club's next primary backup big, behind 2024 lottery pick Donovan Clingan.

Of course, the heartwarming move was Portland's decision to sign another oft-hurt, 35-year-old former All-Star, Damian Lillard, on a three-year deal. The 6-foot-2 Weber State product — who spent 2012-23 in Portland — is recovering from an Achilles tear, and will likely miss the entire season. But when he comes back, the Trail Blazers' backcourt could look crowded.

Or maybe not.

Sharpe is eligible for an extension on his rookie-scale contract this offseason, before Oct. 20.

Will Portland Pay Shaedon Sharpe This Fall?

An athletic, dunk-tastic shooting guard, Sharpe has fitfully seemed to have enticing upside over the past few seasons. But he has been supplanted as the Trail Blazers' best possible young future star by forwards Deni Avdija and Toumani Camara, both of whom enjoyed breakout runs last year.

It's unclear exactly what kind of market Sharpe will face in 2026 were he to hit restricted free agency. More teams should have cap room to at least offer him a sizable deal, which Portland would be able to match. It seems likely that, given their interest in Lillard and Holiday still playing big minutes going forward, the Trail Blazers will wait to let him taste the market, rather than overpay him now. But time will tell.

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