2. Brandon Ingram
Another lengthy wing the Blazers could trade Simons for to help fit their roster needs is the 6-foot-8 New Orleans Pelicans forward Brandon Ingram. Ingram isn't quite the defender Bridges is, but he has more playmaking ability. Ingram's ability to initiate the offense makes him better equipped to be a go-to player. He could be the foundational piece the Blazers build around, giving Rip City a bonafide star on their roster that currently doesn't have one yet.
Additionally, Ingram's playmaking could help bridge the gap for the Blazers, allowing them to move Simons and Malcolm Brogdon without sacrificing as much offense. They could rely on Ingram to take on more of the offensive burden while they wait for Scoot Henderson to develop his efficiency and decision-making.
Surprisingly, Ingram is a more average three-point shooter than you'd expect from watching him play, connecting on only 35.5 percent of threes this season; this is one aspect of his game that doesn't particularly help the Blazers, who desperately need better floor spacing. But the pros still outweigh the cons for the Blazers moving Simons in a package for Ingram.
At only 26 years old, Ingram still has some untapped potential in his game. His increased role in Portland as the clear-cut first option could benefit both parties.