The Portland Trail Blazers inked Jerami Grant to a massive five-year, $160 million contract in the summer of 2023. Just one day later, superstar Damian Lillard requested a trade. It's hard to fault Lillard for that decision, as not only did Portland fail to surround him with the necessary pieces to become a contender, but also drafted his successor in Scoot Henderson with the No. 3 overall pick.
After spending two seasons in Milwaukee, Lillard returns home to a Blazers roster that is much better equipped for an eventual postseason run with the way they are constructed. That can largely be attributed to the pieces they acquired from the Lillard trade, such as building blocks Toumani Camara and Deni Avdija, who were acquired either directly or through subsequent moves.
However, one glaring issue limiting Portland's ceiling is that burdensome Grant deal.
Blazers' Jerami Grant disaster has no solution
Grant is coming off a down year, averaging 14.4 points, 3.5 rebounds, and 2.1 assists on 37/37/85 shooting splits. He's owed $102.6 million over the next three years. The salary cap is set to increase by 10 percent, but that doesn't change the fact that this is a nightmare contract, especially under the new CBA.
This is precisely why Portland shouldn't have acquired Jrue Holiday. Grant has rapidly become a negative asset, and it doesn't make sense for a rebuilding Blazers team to attach draft capital to move him. The Blazers will owe Holiday and Grant a combined $73.6 million in the 2027-28 season, assuming both pick up their player options. That will become problematic when Portland has to extend its core pieces, several of which are currently on rookie-scale deals.
Grant's contract creates a catch-22 for the Blazers; they can't afford to add pieces around their existing core, but he also hinders the development of said core, which they can't significantly upgrade.
Given his declining play, the addition of Holiday, and the potential breakout seasons of Henderson and Shaedon Sharpe looming, head coach Chauncey Billups has a difficult but necessary decision to make: bench Grant. That's quite the expensive bench player for a rebuilding team that doesn't match his timeline, but it would be in Portland's best long-term interest, which needs to take precedence.
Grant is arguably the worst contract in the league, so there's no correct answer for handling this situation that Portland finds itself in -- unless you have a time machine and convince general manager Joe Cronin not to re-sign Grant in a half-hearted attempt to keep Lillard around.