After losing in the first round of the playoffs in each of the last two games, the Orlando Magic is expected to explore a massive offseason move.
The Orlando Magic is one of the best young teams at the Eastern Conference, despite not past its first round since 2010. Between Orlando and the Detroit Piston, the East is expected to pass small markets over the next few seasons, but both teams are a few apart from competing for titles.
Magic built around Franz Wagner, Paolo Bancello, and, to a lesser extent, Jalen Thugs is a hard nose defensively oriented team, although he has long struggled with both shooting and scoring.
Some mock deals from various outlets have moved Damian Lillard into magic, but the former Lillard teammate, who doesn’t have a torn Achilles, is a much more sensible fit.
After an injured season for the Suggs and a disappointing first year in Orlando for Kentavious Caldwell Pope, the magic would be wise to bolster their backcourt.
The Suggs can play on and off the ball if they are healthy, and thanks to the remaining defensive chops in the lineup, the magic can add offensively oriented players.
According to one league insider, the Magic is specifically aiming at one player.
“As the new offseason beckoned, another trail blazer is increasingly predicted as Orlando’s target. Lillard’s former Blazers backcourt mate Anfernie Simons,” reported Mark Stein.
“The 25-year-old is from Orlando, who blended in well from a timeline perspective alongside Banchelo and Wagner.”
Simons played only two 70 games in his career this season, averaging 19.3 points and 4.8 assists while earning 36.3% from the Deep. The five starting five, Suggs, Simons, Banchero, Wagner and Wendell Carter Jr., should be enough for the magic to pass the first round.

Simons is a little ahead of the Portland Trail Blazers cores, namely Scoot Henderson, Shadon Sharp and Donovan Klingan. As a result, he has been included in mock transactions and rumors for a long time.
Despite the promising end of last year’s season, the Blazers are still in the middle of rebuilding, and above all, they value their younger assets and draft picks.
Simons is entering his final season of his $100 million extension, and the Blazers, who are plagued by a massive contract, will also want some financial flexibility, or at least what they can get.
Mock Trading Details
- Magic Receipt: Anfernee Simons
- Trail Blazers Receive: Kentavious Caldwell-Pope, Gary Harris, Jett Howard, 2026 1st round pick (swap rights with WSH or PHX), 2026 2nd round pick, 2027 2nd round pick
The Magic cements the starting lineup without sacrificing too much depth, and the Blazers get a younger player on Harris’ expired contract Howard and Caldwell Pope, who has two seasons of deal left.
To sweeten the pot to get back the KCP, the Trail Blazers get two extra second picks, and in the case of the Simons they get the first round pick that can be exchanged for the least advantage of Washington or Phoenix.
Orlando still has seven first round picks, using or saving for bigger deals. Portland can add to his draft pick weapons and continue rebuilding under the supervision of Chauncy Billup.