The Portland Trail Blazers will have to make a difficult decision on Anfernee Simons as early as this summer. His contract is set to expire after next season, but if the Blazers don't deem him to be a long-term piece in their rebuild, it would be in their best interest to move on from their prolific combo guard sooner rather than later.
In a vacuum, he makes sense to keep around, given he provides shooting and playmaking, two areas the Blazers still need help in. Simons also still fits their rebuilding timeline at 25 years old. But as great as Simons has been throughout his seven seasons with Portland, the Blazers seriously need to consider moving on from him.
The reasons for trading Simons outweigh those for keeping him around. Relative to his impact on winning, his next contract is going to be hard to justify. Moving him will also clear the path for Scoot Henderson, who has proven he should be given the keys to the backcourt with his improved play.
One opportunity that could present itself is Simons' long-rumored trade destination: the Orlando Magic.
Blazers should send Simons to Orlando for a first-round pick
Orlando is Simons' hometown area, but more importantly, he'd help address several roster weaknesses for them. They have a promising foundation led by their forward duo of Paolo Banchero and Franz Wagner, but the Magic must do a better job of finding complementary pieces to surround them.
They rank dead last in three-pointers made (10.8) and three-point percentage (30.8). Simons would be an ideal missing piece to their puzzle, providing much-needed floor spacing to provide more room for Banchero and Wagner to operate.
On The Game Theory Podcast, Sam Vecenie and Bryce Simon mentioned the possibility of sending Simons to Orlando this offseason.
"Orlando has two first-round picks this year. If you're Portland and you can get one of those first-round picks and maybe something else that you like for Simons, that's kind of a win," said Vecenie.
The Magic currently have their own first-round pick (No. 15) and the Nuggets' first-round pick (No. 24); they also have a few up-and-coming pieces that could potentially be included in the deal as the "something else," Vecenie refers to, including Anthony Black, Jett Howard, and Cole Anthony.
Black would be the most intriguing of these young backcourt players, given his two-way potential. But regardless of who the player is, if Portland can receive one first-round pick for Simons, it should be considered a win.
The Blazers need to shift their focus toward a backcourt of Henderson and Shaedon Sharpe. Adding their own lottery pick and one of Orlando's first-rounders to this young core would be a giant step in the right direction for their rebuild, even if it comes at the expense of one of their best players.