1. Orlando Magic
All offseason, the Orlando Magic have been the team most frequently linked with Anfernee Simons in a potential trade, and justifiably so. Simons is from the Orlando area (Altamonte Springs) and played at IMG Academy before being drafted by the Blazers. A potential hometown return makes sense for all parties involved.
The Magic recently signed free agent Kentavious Caldwell-Pope, a great addition to bolster their backcourt and add a veteran 3-and-D player. But KCP isn't a playmaker, and the Magic still need to add someone to take some of the playmaking responsibilities off of Paolo Banchero. Simons can contribute offensively both on-ball, initiating offense in pick-and-rolls, and off-ball as a spot-up shooter.
He'd also fit their timeline, as Banchero is 21, Franz Wagner is 22, and Jalen Suggs is 23. Suggs and Jonathan Isaac are the two dream targets the Blazers should try to get from the Magic in a potential Simons deal. However, it is unlikely that Orlando would be willing to part ways with the Gonzaga guard or Florida State forward, both of whom they highly covet. It's much more likely the trade is centered around young players like Anthony Black, Jett Howard, or Cole Anthony and multiple first-round picks.
Simons wants the chance to win as he enters the prime of his NBA career, and the Magic are a dark horse team that will give him a reasonable shot at a deep playoff run with an underrated young core and multiple star players.