3/4. Anfernee Simons and/or Shaedon Sharpe
Shaedon Sharpe and Anfernee Simons are beloved players and are key pieces on a rebuilding team. With the Blazers attempting to build a contender while Lillard is still in his prime, though, Sharpe and/or Simons may not be with Portland next season.
Rather than wait for Sharpe and Simons to fully develop, the Blazers may view them as highly valuable assets that could be used in trade discussions for a superstar player. As talented young players with high upsides, Sharpe and Simons may be the most enticing pieces for any potential trade partner.
If the Blazers truly prioritize a win-now mentality and a superstar becomes available via trade, Sharpe and Simons are the two best players they can offer.
Ultimately, while both players have shown promise and potential and are loved by fans, their value to the Blazers as trade assets may lead to their departure from the team in pursuit of a star player.
Ideally, though, the Blazers retain one of the two to take the shooting pressure off of Dame in the backcourt.