Blazers' scariest roster question will need to be addressed immediately

How confident are we in this position group?
Cleveland Cavaliers v Portland Trail Blazers
Cleveland Cavaliers v Portland Trail Blazers | Alika Jenner/GettyImages

The Portland Trail Blazers backcourt has more questions than answers heading into the 2025-26 season. Jrue Holiday is the presumed starter, but now 35 years old, Holiday's days of being a high-volume starting guard may be over. Next to him will likely be Shaedon Sharpe, who may have the highest upside of anyone on the team but is still a long way from having a consistently positive impact. Then there's Scoot Henderson, who might be entering a crucial season in determining what exactly his future with this team looks like.

So, even the guys who we know will get minutes have plenty of questions. But what about the backup shooting guard spot? Because outside of these three players, there isn't another clear fit in the backcourt.

The Blazers don't need to have perfect fits at each position, and Holiday, Scoot, and Shaedon will eat up most of the minutes in the backcourt. But Holiday missed 20 games last season, Sharpe missed 10, and Scoot missed 16. There will be plenty of minutes up for grabs throughout the season and I don't know who exactly will get them. Blake Wesley? Sidy Cissoko? More ball-handling duties for Toumani Camara? Your guess is as good as mine.

Blazers backcourt doesn't have much depth

If you're wondering, this "fourth guard" role was filled by Dalano Banton last year, and he played 67 games. That's a lot! And entering this year without a clear replacement for that production (which was sometimes really good, randomly) is an odd choice.

Maybe the front office really does have confidence in Wesley or Cissoko. At this point in the Blazers' rebuild, I don't hate that thought. Blake Wesley was a first-round pick in 2022 and looked promising in a very small sample size his rookie year, but his role and impact never improved and the Spurs let him walk after three years. Him playing the Banton role wouldn't be a deteriment to the team because it wouldn't require that much playing time, and any growth from Wesley in that role would be a developmental win.

Cissoko is entering his second year with the Blazers (he played just 60 minutes last year) and his third NBA season but he's still just 21 years old. At 6-foot-6 with a pretty shooting stroke and great strength, he's the exact type of prospect you don't want to give up on until you're 100% sure about him.

Fans might get an early answer on backcourt rotation

If we see any Wesley or Cissoko early on in the season, we'll have our answer on what Chauncey Billups wants to do in the backcourt, but I also think the situation will be fluid throughout the year. If one of them struggles, they'll likely fall out of the rotation entirely.

But with so many questions about the guys who are already guaranteed roster spots, the fourth guard position might end up being a bigger deal than it seems.