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Blazers Offseason Preview: Free Agency, Draft Assets, Damian Lillard's Return and More

By Ryan Phillips Sports Illustrated

Updated April 28, 2026 9:41 PM

The Trail Blazers snuck into the postseason via the play-in tournament, only to get bounced in the first round by Victor Wembanyama and the Spurs. Despite a disappointing exit, things are looking up in Portland as the pieces are in place to build a solid foundation.

Portland went from being a lottery team for four years in a row to reaching the playoffs this season. Two years ago, they won 21 games, and doubled that during the 2025–26 campaign. That's the kind of rapid improvement teams want when they invest in a youth movement. While young guards Shaedon Sharpe and Scoot Henderson, two former lottery picks, both showed flashes this season, a true star emerged.

Deni Avdija had a career year, as he averaged 24.2 points, 6.9 rebounds and 6.7 assists in 33.3 minutes per game. He was a first-time All-Star and has emerged as the team's offensive centerpiece. Sharpe averaged 20.8 points per game and his shot selection improved, while center Donovan Clingan made a big leap from Year 1 to Year 2. Meanwhile, 25-year-old wing Toumani Camara also showed promise in his third season.

There were plenty of negatives, though. The team was inconsistent all season, which is the hallmark of a young squad. Henderson has all-world talent but can be maddeningly up-and-down and struggled with injuries. Perhaps most importantly, they were one of the NBA's worst three-point shooting teams all season and ranked 28th from beyond the arc at 34.3%. That should get a boost with Damian Lillard returning next season, but the team needs to find more shooters.

There is promise with this squad but demonstrable improvements need to be made.

Trail Blazers' 2026 free agents

Trail Blazers big man Robert Williams III is one of Portland's highest profile offseason free agents. | Scott Wachter-Imagn Images

The Blazers are well over the cap heading into next season, even if they release all of their cap holds. They have $170 million committed to the roster, with Jrue Holiday ($34.8 million) and Jerami Grant ($34.2 million) each taking up a huge chunk of that space. That's a lot of money committed to non-star players in their 30s who don't match the current team's timeline. Both guys are signed through the 2027–28 campaign, so I'd expect Portland to attempt to move one or both of them this summer.

As of now, the Blazers will have the mid-level exception available to them to bolster the roster.

Robert Williams III and Matisse Thybulle are both useful role players who are set for free agency and will likely be too expensive to re-sign. Caleb Love is a restricted free agent who played 49 games and averaged 10.4 points per game. A two-way player this season, it wouldn't be a surprise to see Love brought back next year on a cheap deal.

Unrestricted free agents

Robert Williams III
Matisse Thybulle
Blake Wesley

Restricted free agents

Caleb Love

We'll see what the Blazers decide to do. If they can move off of one of their big contract, maybe they bring someone back, but as of now, it wouldn't be shocking if all four impending free agents walked.

Draft assets

Portland has to be kicking itself for not owning its first-round pick this season. Back in 2021, the team surrendered its pick (No. 15) to the Bulls as part of a three-way deal that sent Larry Nance Jr. to the Rose City, while Lauri Markkanen went to the Cavs via sign-and-trade and Derrick Jones went to Chicago along with the Nuggets' protected second-rounder. In hindsight, that was an awful deal.

The Blazers' second-rounder was dealt to the Pelicans in 2021 in exchange for the draft rights to Greg Brown. It was subsequently shipped to the Spurs in another deal. Brown played in 64 total games for the Blazers from 2021 to ‘23. He's now playing in Athens.

Whoops.

Damian Lillard's return and other possible offseason moves

Damian Lillard will return to the court for the Trail Blazers next year, after spending the year recovering from a torn Achilles. He was dealt by Portland to the Bucks in 2023, returning to the Blazers in ‘25. | Jaime Valdez-Imagn Images

Lillard's return should provide a boost to Portland's young backcourt. While you never know how a player in his mid-30s will recover from surgery to repair a ruptured Achilles tendon, at the very least Dame should provide a steady veteran presence, and shooting ability. Lillard is a career 37.1% shooter from deep and hit 37.6% last season for the Bucks.

Grant (38.9%) and Holiday (37.8%) can both hit threes, so if the team does wind up moving one or both guys, it will need to find replacements who can do the same. Avdija (31.8%), and Sharpe (33.7%), take the most shots on the team and are two of its worst three-point shooting regulars. That must be balanced elsewhere in the lineup.

Attempting to work a trade for a player like Nuggets forward Cam Johnson would be the best fit. He's heading into a contract year and his first season with Denver was a disappointment as he averaged 12.2 points, 3.8 rebounds and 2.4 assists in 30.5 minutes per game. He did hit 43.0% of his shots from beyond the arc, so he fits what Portland is looking for. If Denver makes an early exit, it could look to retool its roster, which might open the door for the Blazers.

Whatever happens, Portland needs to continue to push its young players to improve while finding ways to add support pieces and shooting. The youth movement is working and has provided a solid turnaround. It's time to take the next step.

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This article was originally published on www.si.com as Blazers Offseason Preview: Free Agency, Draft Assets, Damian Lillard's Return and More.

This story was originally published April 28, 2026 at 9:27 PM.