2. Can Simons, Sharpe, and Henderson all share the backcourt?
The Blazers haven't had much opportunity to see how these three guards play together. Portland had high expectations for rising star Shaedon Sharpe entering his sophomore campaign, but he was limited to just 32 games after undergoing surgery for a core muscle injury. Sharpe and Scoot Henderson only played 13 games together last season, and Scoot wasn't nearly as efficient during that stretch as he was still adjusting to the NBA competition and pace of play as a rookie.
If the Blazers don't move Simons before training camp, they should reevaluate how effectively all three guards have played with one another. Defensively, the Blazers' backcourt will be a liability if all three stay on the roster. Their frontcourt of defensive-minded players, including Clingan, Williams, Toumani Camara, and Matisse Thybulle, will help compensate. Still, it's a matter of how much their help defense can really make an impact if they still have multiple defensive liabilities in the backcourt.
The Blazers seem set on making Henderson and Sharpe the focal points of their rebuild, and rightfully so. But if Simons hinders their progression, Portland should heavily pursue trades for him at the deadline.