Last summer, Aaron Fentress of The Oregonian stated that trading away one of Anfernee Simons or Jerami Grant before training camp was the Portland Trail Blazers' goal. Roughly one year later, Portland finally achieved that goal by shipping Simons to the Boston Celtics.
It's unsurprising that Grant remains on the Blazers roster because, well, he's the one who's impossible to move. Simons is on an expiring contract and made financial sense for Boston to acquire to get under the second apron. Meanwhile, Grant is arguably on the worst contract in the entire association.
How Jerami Grant threatens Portland's rebuilding timeline
Portland signed Grant to a massive five-year, $160 million deal back in 2023 and still owes him $102.6 million over the next three seasons. ESPN's Zach Kram deemed it the Blazers' worst move in recent history, and it's hard to argue with that.
"Grant's contract hasn't gotten in the way of any other Trail Blazers moves yet -- but with the Blazers rising, Jrue Holiday's hefty deal now in the fold and Grant still owed another $102.6 million over the next three seasons, it might soon prove a tricky roster-building obstacle," wrote Kram.
Combine the new CBA with Grant's declining play (14.4 points and 3.5 rebounds on 37/37/85 shooting splits last season), and it's easy to see how Portland has a negative asset.
One way to solve this problem would be to attach future assets to offload his salary, but the Blazers don't want to do that at this point in their rebuild, which is apparent by the fact that he's still on the roster heading into the 2025-26 season. That leaves Portland with one of two options: start a rapidly declining veteran over a key rebuilding component such as Scoot Henderson or Shaedon Sharpe, or pay Grant north of $100 million to bring him off the bench.
The latter is the lesser of two evils, as the Blazers need to prioritize their youth more. Still, this is a dilemma that could haunt Portland for the next three years, and could potentially worsen as the 31-year-old Grant ages while his annual salary increases. They're going to owe him $36.4 million in the 2027-28 season, which, as Kram notes, could get in the way of retaining key pieces of their young core.
This may not even seem like a significant problem, yet, because of Portland's projected cap space with so many team-friendly and rookie-scale deals. But it inevitably will be. This is a problem that training camp or next season can't solve; it's far beyond that. Grant could have a relative bounce-back year, but it still wouldn't justify his contract or get the Blazers out of this situation.