What Offseason Moves Would Help the Trail Blazers' Longevity?

The Portland Trail Blazers have a prime opportunity to maximize their window of championship potential. All-Star Deni Avdija is on one of the best-valued contracts in the NBA. Donavan Clingan and Scoot Henderson are still on rookie deals. Shaedon Sharpe signed an affordable rookie extension, and Toumani Camara signed an affordable veteran extension. Despite having so many good contracts, around 42% of the Blazers' cap is taken up by two players in their 30s: Jerami Grant and Jrue Holiday.

Grant was the Blazers' most consistent three-point shooter this year, was the third leading scorer, and averaged nearly 30 minutes a game. He was very productive, but as a 32-year-old with a $34 million cap hit in 2026-2027, Grant's contract does not help the Blazers build around their young core. Those 30 minutes per game could give younger players some more opportunities to develop, and that cap space could be used to invest in the future through rookie extensions for Clingan and Henderson, or eventual veteran extensions for Avdija, Camara, and Sharpe. Trading Grant for a veteran on an expiring contract or trading him in a salary dump would help the Blazers continue to build for the future.

After two difficult seasons in Boston, Jrue Holiday found his footing again as a 35-year-old in Portland. Holiday's trade value will likely get no higher, so now would be a great time to send him to a championship contender for a young, controllable player or draft compensation. Trading Grant and Holiday would create $69 million in cap space, which would be best used in extensions for their young core.

Scoot Henderson just completed his third season in the NBA and will be eligible to sign a rookie extension beginning July 1. Players who are drafted in the first round are signed to a four-year contract. Once their rookie contract expires, they become restricted free agents (RFA). Other teams are allowed to submit offer sheets for these players, and their most recent team can choose to match the offer. Teams can avoid this process by signing players to a long-term extension when they have one year remaining on their rookie contract.

Henderson's extension could look similar to the 4-year, $90 million extension that Sharpe signed in October 2025. That would give Henderson around a $20 million cap hit beginning in 2027-2028. Of course, there is a possibility that Portland isn't ready to offer a big extension, and it's possible that Henderson would rather wait and test the RFA waters. If he makes the leap to an All-NBA player, he would be eligible for an extension worth 30% of the salary, or nearly $50 million per year. If both parties can't agree on an extension during the offseason, Henderson's play during the 2026-2027 season will largely impact the overall value of his next contract.

Deni Avdija now has two years left on his contract, which makes him eligible for a veteran extension starting October 1. Given his all-star appearance in year 2 of his contract, Avdija is expected to command a large extension, making it of high importance to offload those large Jerami Grant and Jrue Holiday contracts sooner rather than later.