2. Shaedon Sharpe
If head coach Chauncey Billups elects to start Henderson at the starting point guard spot, then Sharpe will likely be the odd man out of the starting lineup, with Simons sliding to the shooting guard position. This lineup would look like:
PG: Scoot Henderson
SG: Anfernee Simons
SF: Deni Avdija
PF: Jerami Grant
C: Deandre Ayton
Blazers general manager Joe Cronin previously said in a press conference that the Blazers are committed to building around Henderson and Sharpe, with no mention of Simons. With Portland wanting to focus on their youth movement and surrounding Henderson and Sharpe with complementary talent, Simons is more expendable. Trading him away would solve the issue of having to decide whose starting role to take away between arguably the Blazers' two most promising young pieces.
But the fact that Simons is a combo guard and Avdija can play multiple positions with his 6-foot-9 frame and versatility gives Billups more lineup flexibility. Sharpe and Henderson can essentially come in for each other, with Simons playing both guard positions. If they want to go smaller and play their guard trio together, Avidja is more than capable of spelling Grant at times and playing power forward.
Most importantly, trading away Malcolm Brogdon cleared up their backcourt logjam. Although one of Henderson and Sharpe likely won't start, they both should see significant minutes and be focal points of their offense in what could be a breakout year for both players.