2. Trade Simons for Anthony Black package
The Blazers could also trade Henderson to the Orlando Magic, who are in need of a point guard. However, in this scenario, Scoot is struggling to play well, which would hinder his trade value.
Additionally, Simons fits their team much better. Besides being from the Orlando area, there's a basketball reason Simons was linked to the Magic all summer (mainly in mock trade proposals). Orlando is in win-now mode and could benefit from adding a secondary playmaker like Simons, who is more established and a better shooter than Scoot.
The Blazers could be more inclined to make a potential deal with the Magic if Scoot is struggling and if they only view Simons as more of a combo guard rather than their long-term answer at point guard. Not to mention the possibility of Simons being discontent should the Blazers have another season close to 21 wins.
Despite it being constantly talked about this summer, there hasn't been anything recently to suggest that a trade like this would get done anytime soon. But if the Blazers do happen to make a trade with the Magic, they should prioritize Anthony Black over Cole Anthony.
Black isn't nearly the level of player Simons is, so the package would have to include significant draft capital as well, perhaps in the form of two first-round picks. And while he doesn't jump off the page as someone with All-Star-level potential like the Blazers' backcourt trio has, Black would be a great addition as a role player. He's just 20 years old, a recent No. 6 overall pick (2023), and is a solid two-way guard given his 6-foot-7 size and athleticism.
Black wouldn't make up for what the Blazers would miss in Simons, but this type of deal could better position them to address the point guard position in the future between him and future draft capital.