The Orlando Magic's season ended in the first round of the NBA playoffs for the second consecutive season, and that likely means Orlando will take a swing this offseason.

While the Magic have proved to be a tough team to beat over the past two years, they have notably lacked creation and shooting in the backcourt that is often needed among contenders. With a call to Portland, though, some of those woes can be addressed.

“When Damian Lillard was on the trade block in Portland before the 2023-24 season, league sources say that more than a few rival teams — as well as Lillard's camp — wondered whether Orlando would be joining the trade pursuit for him,” Jake Fischer and Marc Stein wrote for The Stein Line.

“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 [Paolo] Banchero (22) and [Franz] Wagner (23).”

Although Simons posted his 3-point percentage this past season in the last five years, he is a career 38.1% 3-point shooter and consistently among the best free-throw shooters, which could be a sign that he can improve his perimeter shooting numbers with a different role outside of Portland. Additionally, Simons has averaged 4.5 assists over the last four seasons.

Simons would certainly be an immediate boost to the Magic's offense, which was the fourth-worst in terms of rating. The three teams behind them were the Washington Wizards, Charlotte Hornets, and Brooklyn Nets, who went a combined 63-183 this season. The offensive rating for Orlando was so bad, in fact, that the team's net rating was -0.2 despite posting the second-best defensive rating (109.1) in the NBA.

Part of the Magic's offensive troubles likely stemmed from injuries to Jalen Suggs and Mo Wagner. Suggs, in particular, averaged a career-high 16.2 points per game, as well as 3.7 assists, before going down with a season-ending injury in January. Off the bench, Wagner was averaging a career-high 12.9 points and shot 36.0% on 3-pointers before tearing his ACL in December.

In addition to the Magic's troubles, the Blazers could feel motivated to make the deal.

“Teams have called the Blazers about Simons in the past, but there has never been an immediate sense that he was close to being dealt. That could change in the offseason, as Simons will be entering the final year of his contract and making $27.7 million,” ClutchPoints' Brett Siegel wrote.

Simons, a native of Altamonte Springs, Florida who attended high school in Orlando, is set to be an unrestricted free agent in 2026 at age 27.