SG: Shaedon Sharpe
Sharpe appears more likely to start over Henderson if one of Simons or Grant doesn't get traded before the start of the regular season. He has more experience in the NBA, is now entering his third season, and has shown flashes of his elite potential when healthy. Sharpe was limited to only 32 games last season due to a core muscle injury but averaged 15.9 points per game in that span.
Many expected Sharpe to have a breakout sophomore season, but he is poised to have it in his third season. If Sharpe produces at a high level, as many expect, it will be extremely difficult for head coach Chauncey Billups (or whoever ends up being the coach in 2025-26) not to start Sharpe. He has arguably the highest ceiling of any Blazers player on their roster, and it would be a disservice not to make Sharpe one of the main pieces of their rebuilding efforts.
Henderson and Sharpe should get significant minutes next season regardless of who starts, but it would be shocking if both of them don't get the keys to the franchise by the 2025-26 season at the latest.