3. Anfernee Simons
On the one hand, Anfernee Simons fits the Blazers' rebuild, as he's only 24 years old. He had another productive season, averaging 22.6 points, 5.5 assists, and 3.6 rebounds per game. It's difficult to trade away one of your franchise's most promising players amid a rebuild. Especially when considering that the Blazers were bottom of the league in three-point efficiency at 34.4 percent, and Simons is a career 38.6 percent shooter from beyond the arc.
On the other hand, even if Portland moves Malcolm Brogdon, something else has to give with the Blazers' log jam at the guard position. Scoot Henderson, Anfernee Simons, and Shaedon Sharpe can't effectively coexist as their backcourt of the future. While all individually talented players, the trio isn't built for the physicality of the NBA playoffs. The Blazers have a similar problem as they did with Damian Lillard and CJ McCollum, with their lack of size hindering their team's defensive upside.
Simons has also said he "wants the opportunity to win" heading into year seven of his NBA career, per Sean Highkin on X. Unfortunately, Portland isn't winning anything significant anytime soon. Moving him before his trade value drops after a formal trade request may be better for getting ahead of Simons' potential discontent.