The Portland Trail Blazers are a rebuilding team in flux. They have multiple established players involved in trade rumors, including Anfernee Simons, Jerami Grant, and, to a lesser extent, Deandre Ayton, Matisse Thybulle, and Robert Williams III. Of these seemingly available players, Simons has the highest trade value around the league and should net the Blazers the most in any potential return. He's just entering his prime and, on a relatively team-friendly contract, owed $25.9 million this upcoming season.
A rebuilding team like the Blazers would typically consider a 25-year-old coming off a season in which he averaged 22.6 points per game as a focal point of their rebuild. However, they are in a unique position where their two highest-upside players, Scoot Henderson and Shaedon Sharpe, are both guards. Given Simons' trade value and Portland's emphasis on rebuilding around Scoot and Sharpe, a Simons trade seems likely at some point. But it remains to be seen if one will happen before training camp.
Simons is entering his seventh season and wants the opportunity to win. Because of this, a few rebuilding teams in need of a sharpshooting combo guard can be eliminated from the conversation for the best match for a potential trade partner, including the Brooklyn Nets, Detroit Pistons, Charlotte Hornets, Washington Wizards, and Utah Jazz. Still, this isn't to say it's impossible in the excitingly unpredictable NBA landscape. Remember when Damian Lillard was supposed to go to the Miami Heat?
Honorable mention - Miami Heat
Speaking of the Heat, if they had significant interest in Lillard, why wouldn't they want a younger, cheaper alternative in Simons? With two-way stars Jimmy Butler and Bam Adebayo, they are well-equipped to compensate for Simons' defensive weaknesses.
But the Heat added another combo guard, Terry Rozier, who, like Simons, offers a microwave scoring ability and flashes of playmaking. Additionally, the Blazers' decision to spurn the Heat and trade Lillard to an Eastern Conference rival, the Bucks, may have weakened the trade relationships between the two teams.
Although they are strikingly similar players, Simons is a worse version of arguably the Blazers' best player in franchise history. Miami might not be inclined to give up significant assets for Simons if they don't think he's the piece that will put them amongst the elite teams in the improved Eastern Conference.