2026 should signal a year of change for the Portland Trail Blazers. Tom Dundon is set to take over as owner, and Damian Lillard will even be suiting up this year. It's an exciting time for Blazers fans eager to see their team return to the postseason. But before the Blazers' sale becomes official and Lillard makes his storybook return, the first order of business is the Feb. 5 trade deadline.
Portland was only one of a few teams to sit out last season, but is expected to be a potential buyer this time around. Robert Williams III should be considered the most likely trade candidate given his expiring contract, among other factors. But with roughly one month to go until the deadline, the most significant question pertains to Jerami Grant.
The Portland Trail Blazers could finally trade Jerami Grant
What Portland decides to do with veterans such as Williams or Matisse Thybulle at the deadline isn't as much of a franchise-altering decision as Grant, largely because of his contract. The Blazers still owe Grant $102.6 million over the next three seasons.
He's played drastically better this season, averaging 20.0 points, 4.0 rebounds, and 2.7 assists on 44/39/87 shooting splits. With his stock rising, now could be a golden opportunity for Portland to finally get rid of its negative asset.
Grant has been linked to the Milwaukee Bucks (subscription required), according to NBA insider Jake Fischer on The Stein Line. It's hilarious, considering Milwaukee is looking to go "big game hunting," yet the targets are just... Zach LaVine and Grant, among others.
The Bucks could be digging themselves a deeper hole to try to keep Giannis Antetokounmpo around by trading for someone like Grant. He's not a needle-mover, but he has a massive contract that would prevent them from further upgrading the roster.
That could be a win-win for Portland. They get off the three years remaining of Grant's five-year, $160 million deal while also potentially increasing the value of the future draft capital Milwaukee owes them from the blockbuster Damian Lillard trade.
It remains to be seen whether Portland will actually move Grant by February, especially since he's considered a favorite of general manager Joe Cronin. But Grant was in the midst of a bounce-back season prior to his injury, which means it's an ideal window for the Blazers to offload his massive contract.
That may not be ideal for their short-term playoff hopes, but Portland needs to continue making its long-term outlook a top priority. Their finances are going to be more constrained after bringing in Jrue Holiday this summer, and they need to proactively make moves to ensure they can eventually renegotiate and extend Deni Avdija's team-friendly contract that he's significantly outplaying.
Whether it's Milwaukee or another team, Portland must actively explore trades for its overpaid veteran forward.