Blazers Facing Pivotal Offseason With Key Contracts Looming

The Portland Trail Blazers are a team still building, even if no one quite knows what they’re building toward.

They enter the offseason with 10 players either eligible for an extension or entering the final year of their deal. That’s not a typo. Ten.

That kind of roster flux would be enough to keep any front office awake, but for general manager Joe Cronin and company, the decisions go beyond numbers and cap space. As Rose Garden Report’s Sean Highkin notes, these choices could help define the next era — or simply prolong the current one.

Start with Anfernee Simons. Just 26 years old, he’s not a budding prospect anymore. He is what teams hope their young guards become — a reliable, high-level scorer with a handle, a jumper, and a head on his shoulders.

But he’s also caught in a numbers game. Scoot Henderson is the face of the future. Shaedon Sharpe is the high-flying enigma. If either is going to take the reins, Simons might need to be moved.

The problem? He’s good. Really good. And unlike some names that bounce around in summer trade rumors, Simons actually produces.

So while fans in other cities might circle him in hypothetical trades, the Blazers are under no pressure to deal him, and probably shouldn’t.

Then there’s Deandre Ayton. The 7-footer is polarizing, both in Portland and across the league. He puts up numbers, rebounds when he wants to, and shows flashes of dominance.

But his presence also blocks former No. 7 overall pick Donovan Clingan from a starting role. That’s not a small wrinkle. Still, Ayton’s trade value may not match his utility to a team still learning how to win.

If you’re looking for real mystery, it’s with the kids — Sharpe and Toumani Camara.

Sharpe’s talent is obvious. He jumps out of the gym, can create his own shot, and looks like a future star in warmups.

But the game isn’t played in warmups. Inconsistency, injuries, and lapses in focus have stunted his rise. That makes an early extension tough to peg. Too much and it’s a gamble. Too little and he’s insulted.

Camara is a different kind of bet. He made the All-Defensive Second Team and already guards the other team’s best player like it’s personal.

The Blazers could offer something in the $90 million range over four years. But Camara might wait. Bet on himself. Grind through another season and see if someone throws $100 million at him next July. That’s not far-fetched, not in today’s NBA.

So no, Portland may not be making splashy free-agent moves this summer. But don’t mistake that for a quiet offseason. This one’s about choices, about vision, development, and deciding who’s really part of what they’re building.

And if they guess wrong? The rebuild gets a little longer.