Portland Trail Blazers fans have long heard of the potential ties between Anfernee Simons and the Orlando Magic. Most of that speculation has stemmed from Orlando being his hometown area and the obvious fit for a team in dire need of more shooting and playmaking. But with NBA insider Marc Stein's latest intel, there's finally some real substance linking the two parties.
"As a new offseason beckons, another Trail Blazer has been increasingly projected as an Orlando target: Lillard's former Blazers backcourt mate Anfernee Simons. The 25-year-old is an Orlando native who would certainly blend in nicely from a timeline perspective alongside Banchero (22) and Wagner (23)," wrote Stein.
An Anfernee Simons trade makes perfect sense for everyone involved
Stein notes that the Magic were a team that others around the league (and Damian Lillard's camp) were monitoring as a potential team to join in on the Lillard sweepstakes after he requested a trade in 2023.
A Lillard-Magic pairing would have solved many of their backcourt and offensive problems, but it wasn't a perfect fit for their timeline. Orlando was coming off a 34-48 record in the 2022-23 season, and it didn't make sense for them to accelerate their rebuild in an aggresive move for an aging Lillard.
But if it wasn't Lillard they traded for, it was apparent that the Magic needed to do something. Years later, the same issues continue to plague their roster, making it even more surprising that they joined Portland as one of the few teams to stand pat at the February trade deadline.
Simons is Lillard-lite as he has eerily similar strengths, weaknesses, and style of play. And now, the Magic are better equipped to make a trade to complement the ascending Franz Wagner and Paolo Banchero.
From the Blazers' standpoint, it makes sense for them to part ways with Simons despite him being one of their best players and just entering his prime at 25. His contract is set to expire after next season, and Portland should preserve its cap flexibility to make a splash for a star who will move the needle and impact winning more than Simons.
What should the Blazers look to get in return?
The Magic are the Eastern Conference version of the Blazers. Both teams have a promising wing/forward duo, length, defense, athleticism, and a few promising yet unproven backcourt pieces.
The most challenging part about potentially trading Simons is that Portland, like Orlando, still needs more playmaking and shooting help, ranking bottom five in three-point percentage the past two seasons. Getting some shooting back in the form of Jett Howard or Cole Anthony could be tempting, but both players lack the ceiling that Portland should be seeking.
Higher-upside players they should target include Jonathan Isaac and Anthony Black, or they could find that talent in the draft. Orlando is projected to have the No. 16 and No. 25 picks (via Denver) in the upcoming draft.
In a perfect world, the Blazers would land one of Black or Isaac and the No. 16 pick, giving them a shot at adding a prospect like Collin Murray-Boyles, Egor Demin, or Jase Richardson to address multiple roster needs.
Even if his value doesn't reach that level, it's in Portland's best interest to get as much as they can for Simons this summer. They should want to get ahead of this before they're forced to choose between overpaying or letting him walk for nothing.