Portland Trail Blazers Offseason Preview

The New York Knicks have won their first championship since 1973, leaving the Portland Trail Blazers with the longest active title drought in the NBA. Next season will mark 50 years since Portland’s last title, and the front office is looking to build a roster that can contend in the Western Conference. Now that the Finals have concluded, teams can officially begin exclusive extension negotiations with players on expiring contracts who are bound for free agency.

The Blazers currently have 10 players under standard contracts for the 2026-2027 season: Deni Avdija, Toumani Camara, Donovan Clingan, Jerami Grant, Scoot Henderson, Jrue Holiday, Damian Lillard, Kris Murray, Shaedon Sharpe, and Yang Hansen. Vit Krejci and Sidy Cissoko are under non-guaranteed contracts, while Jayson Kent and Chris Youngblood are under two-way contracts. Assuming that Krejci and Cissoko are back with the team next year, the Blazers will have only three roster spots and one two-way spots open.

The Blazers are currently over the cap, but are under the first luxury apron by over $30 million. They also have $15 million in non-tax payer mid-level exception (MLE) and $5.5 million in bi-level exception. That gives the team plenty of flexibility to sign Robert Williams III and Matisse Thybulle.

“The biggest challenge with re-signing Thybulle is that the Blazers are packed full of players at his positions, writes Keith Smith in Spotrac’s Blazers offseason preview. “He’s a true wing and that has him behind Deni Avdija, Toumani Camara, Jerami Grant, Shaedon Sharpe and even Jrue Holiday (when he’s in an off-ball role) in Portland’s pecking order. That’s a lot of guys. Is Thybulle worth paying $8 to $10 million? Probably. He’s a real 3&D player. Is it worth the Blazers giving him that kind of deal? Maybe not.”

Caleb Love has possibly played himself into a standard contract that could also fit under the MLE. “Sometimes two-way players go overlooked as important free agents, but Caleb Love proved last season that he can play,” Smith said. “Portland should do what they can to either get Love on the roster this year on a long-term standard deal. Or they can bring him back on a two-way contract to open the season, then eventually have a plan to convert Love to a standard deal in-season. He’s an ideal third or fourth point guard.”

Prediction: Robert Williams III, Matisse Thybulle, and Caleb Love sign through the 2026-2027 season and the Blazers sign an undrafted free agent to their open two-spot.