The Portland Trail Blazers have their first All-Star since Damian Lillard in Deni Avdija. That alone has made this 2025-26 season a success, as Portland has finally found that star they've been missing throughout this entire rebuild.
One downside of Portland stealing Avdija from the Washington Wizards is that he's on such a team-friendly deal that he's massively outplaying it. That complicates a future extension as they'll first have to renegotiate his existing contract and then extend off that new figure.
Portland will face a challenge retaining its promising young core, but an obvious proactive solution is trading one of its two most expensive players: Jrue Holiday or Jerami Grant.
Jerami Grant continues to complicate the Blazers' financial outlook
In a perfect world, the ideal solution would be to trade Grant, keeping Holiday as that bridge between their two timelines. He impacts winning now and also provides a veteran presence to help mentor their youth, particularly in the backcourt, which need more consistency.
But unfortunately, Grant's overpaid contract is a major roadblock to that becoming a reality.
He's on the books for $34.2 million next season with a $36.4 million player opt-in in 2027-28. Grant did have a relative bounce-back season in Portland, providing the second unit with scoring, shot-creation, and floor spacing. But that's a one-dimensional skillset, and the fact that he took on a sixth man role for a 42-win team isn't necessarily a compelling enough case to justify a team taking on his salary.
The reality is, Grant is still a negative asset around the league. Portland may even have to attach a first-round pick or two to incentivize a team to take on the overpaid veteran.
He hasn't fit the Blazers' rebuild, which was apparent on the very day after he signed a five-year, $160 million deal with Damian Lillard requesting a trade. But the Blazers, taking a patient rebuild approach, haven't yet felt the sense of urgency to attach future assets to offload Grant's salary.
At one point, they even had a chance to turn him into assets of their own, but GM Joe Cronin's asking price of two first-round picks backfired spectacularly.
Despite Grant's resurgence, the idea of Portland potentially coming away with anything of value for Grant is a ship that has sailed. It's now going to cost them in a major way, whether that means having to trade the more valuable Holiday instead, or attach future assets of their own to finally solve the Grant dilemma once and for all.
Portland is suddenly at a crossroads in its rebuild. Their conflicting timelines aren't sustainable, and eventually something has to give, even from a purely financial standpoint. The easiest solution to that problem is a long-overdue Grant trade. But Portland could very well find the market overwhelming, as they've held onto the expensive veteran for far too long.
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