Blazers Have Massive Trade Chip to Use This Offseason

The Portland Trail Blazers find themselves in a very interesting spot as it pertains to young guard Anfernee Simons.

The soon-to-be 26-year-old is approaching the final year of a 4-year/$100 million contract he signed with the Blazers a few years ago. There are questions as to whether Portland will commit heavy money to keep him in the fold.

Fellow point guard Scoot Henderson finally showed some real promise for a longer stretch of the season this past year. There are some who contend that Henderson may be more of a true facilitator as opposed to Simons, who's very much a combo guard.

Alongside both players is Shaedon Sharpe — most probably the youngest Blazer on the team with All-Star upside. Sharpe and Simons could be a very dynamic pairing for years to come, though there's also a thought that Sharpe could benefit further from playing alongside a pass-first player.

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Longtime writer Aaron Fentress of OregonLive went into a deep dive on the young guard. Fentress broke down the postivies Simons brings to the table. He also delved into his possible future — and if it makes sense for the Blazers to keep him. Either way, it appears as if he'd have some real interest from other teams.

"Solid. [Anfernee] Simons’ track record overrides his somewhat down season. He is quick, fast, explosive and can score from all levels. Is he a starter on a contender? Tough to say. But at the very least, Simons would provide any team with instant offense off the bench with the ability to play both guard positions and start when needed."

Anfernee Simons is a name to watch for the Orlando Magic, per @TheSteinLine

“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… pic.twitter.com/BcIZLdxIk0
— NBACentral (@TheDunkCentral) May 5, 2025

Portland does have some real flexibility here. Going into the year without some clarity, whether it be a trade or an extension, could get messy, as it naturally is with many impending free agents.

Signing Simons to an extension wouldn't be the worst thing in the world, either. Portland would benefit from the start of his prime years while pinning down a real asset that could be used in a future trade down the line.

Could the Portland Trail Blazers send Anfernee Simons from #RipCity back to his hometown to play for the Orlando Magic?@DannyMarang says discussions about it have already happened pic.twitter.com/oO9HkG3Z3B
— 1080 The FAN (@1080TheFAN) May 6, 2025

There most certainly will be a market for an explosive guard in their mid-20s with the ability to score at all three levels. At the very worst, you're looking at a guy who could become one of the best sixth men options in the league, if not a very credible starting guard.

For Portland, it's a bit of a win-win situation assuming he's either re-signed or traded. Letting him walk without recouping anything would be disappointing. If it's deemed internally that Simons would not re-sign, look for a host of team's — specifically Simons' hometown — to be in the mix.

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