The Trail Blazers have had a surprising offseason, leaving head coach Chauncey Billups with a difficult decision regarding who Portland's starters will be heading into the 2025-26 season. Does he lean into their win-now approach with veterans Jerami Grant and Jrue Holiday? Or have Scoot Henderson and Shaedon Sharpe shown enough progress to fully embrace the youth movement? Perhaps the answer is a combination of these extremes, resembling Portland's unique two-timeline roster.
But one thing is for certain: Billups loves his defense. And for that reason, Sharpe is fighting an uphill battle to crack the starting unit more than the others.
Shaedon Sharpe's uphill battle for a starting spot
It wouldn't make sense for Portland to take on Holiday's $104 million salary just to bring him off the bench. Henderson has the most pedigree as a former No. 3 overall pick, and Portland's offense desperately needs more ballhandlers and playmakers. Grant, well, quite frankly, shouldn't start. But Billups tends to lean on his veterans, arguably at the expense of Portland's future. If Grant does start, the silver lining is that he can't be worse than last season. Grant himself admitted to having a down year, and should be due for positive regression in 2025-26. The hardest one to see a viable starting pathway for is Sharpe.
Sharpe certainly still has a case of his own to make. For one, he has arguably the highest ceiling of anyone on Portland's roster, which should be a top priority at this stage in their rebuild. He also emerged as the Blazers' secondary option down the stretch of last season, including a red-hot month of April in which he averaged 28.8 points, 7.2 rebounds, and 4.8 assists. That offensive firepower will take some of the burden off of Deni Avdija, which is something Portland needs to address with score-first players Anfernee Simons, Deandre Ayton, and Dalano Banton out of the picture.
Not to mention, Sharpe is set to hit restricted free agency next summer if Portland doesn't extend him before the start of the season. Similar to the argument for starting Henderson to evaluate him in an increased role before Damian Lillard returns, Portland must also see what they have in Sharpe before committing to him long-term.
That's what the Blazers should do. However, Billups and general manager Joe Cronin share an aligned vision for Portland's roster. They are way behind the Western Conference in star power and want to be elite defensively to gain ground.
With Simons no longer in Portland, Sharpe is now the team's worst defender, with a defensive rating of 117.2 this past season. That glaring flaw in Sharpe's game was already a problem for Billups last season, who openly benched him after 31 starts for that exact reason.
The good news is that Sharpe is just 22 years old. He continues to trend in the right direction and, hopefully, will make strides as a more consistent three-point shooter and defender. Sharpe has the physical tools with his 6-foot-5 frame and elite athleticism to become a stout defender. But the Blazers have taken an "earned, not given" approach with their starting lineup. And it wouldn't be surprising if Sharpe has to come off the bench until he proves his worth as an impactful two-way player.