The Portland Trail Blazers are faced with a challenging offseason ahead, and one of the most difficult decisions general manager Joe Cronin will have to make will be whether or not to move one of their best players, Anfernee Simons. After last year’s rollercoaster offseason, highlighted by the Damian Lillard blockbuster trade and subsequent Jrue Holiday deal, the Blazers find themselves at a crossroads again.

It’s a similar situation to last offseason, only to a lesser extent. Yet again, their backcourt is too crowded between Simons, Malcolm Brogdon, Scoot Henderson, and Shaedon Sharpe. With Henderson and Sharpe seemingly being the backcourt duo of the future, Simons’ role and long-term status as a member of the Blazers are in flux.

The following trades are with teams identified as ones that could greatly benefit from Simons’ combo guard abilities, particularly on offense. In all four trades, the Blazers continue their post-Lillard teardown in the form of draft capital, young assets, or a combination of the two.

1. Orlando Magic finally get their guard of the future

The Orlando Magic are seemingly the most popular landing spot for Anfernee Simons. The Magic and Blazers make much sense as potential trade partners in a Simons deal. Following Orlando’s first-round playoff exit, Paolo Banchero told The Washington Post’s Ben Golliver what the team needed to address this offseason.

Simons is more of a combo guard than a traditional pass-first point guard. But, besides that, his game is highly similar to what Banchero mentioned the team is looking to add this offseason. Simons and Banchero could split the role of offensive initiator, and the two would play well off each other; Simons could provide much-needed floor spacing as a career 38.5 percent three-point shooter.

Meanwhile, Portland potentially gets three first-round picks in return. Although, if all three of them conveyed, they’d likely be mid-to-late first-round picks. For this draft in particular, it would give the Blazers another opportunity to address another positional need at pick No. 18. For instance, if they draft two wings (or a wing and a guard) with their first two lottery picks, it would make sense for them to target a big like Zach Edey, Kel’el Ware, or Yves Missi with their additional first-round pick in this scenario.

2. San Antonio Spurs add a better fit for Wemby

Similarly to the Magic, the Spurs make a lot of sense as a potential offseason trade partner with the Blazers. A deal centered around Keldon Johnson in exchange for one of Portland’s guards, either Simons or Malcolm Brogdon, could benefit both parties. The Blazers have a stockpile of guards and could be interested in a well-rounded forward like Johnson to balance their roster better.

Meanwhile, the Spurs desperately need a playmaking guard to get Wembanyama as much help as possible. Simons would be intriguing for San Antonio due to his elite shooting, making it more difficult for teams to double-team Wemby. Because Simons is perceived to have more trade value than Johnson, it makes sense to swap either of the team’s two lottery picks in this upcoming draft.

At No. 4, the Blazers could potentially get Donovan Clingan, who they supposedly are high on. If they decided to trade up for No. 8 instead, Portland could take two back-to-back high upside swings. Some possible prospects include Ron Holland, Cody Williams, or Tidjane Saluan, none of which are guaranteed to still be around at the end of the lottery, especially in this unpredictable draft.