10 Worst Portland Trail Blazers moves of the Joe Cronin era

3. Overpaying Jerami Grant

The Blazers were desperate when free agency opened in 2023. They gave up one first-round draft pick and two second-rounders to acquire him just one year earlier. Portland did not want that to be for just one season, especially a year where they won 33 games and missed the playoffs.

The Trail Blazers also knew they had to do whatever they could to keep Damian Lillard happy. He wanted roster improvements, so they could not lose Grant for zero return if they hoped to keep one of the franchise’s GOATs.

Those factors gave Grant all the leverage and the 6’8 forward cashed in with a five-year $160 million contract. He will be tied for the 36th-highest-paid player next season, despite never being an All-Star. Grant is set to make more than Devin Booker, Jamal Murray, DeMar DeRozan, Jaylen Brown, and Jalen Brunson in 2024.

To make matters worse, Lillard requested a trade before Grant officially signed the deal. The Portland Trail Blazers could not go back on their word. Grant will be the team’s highest-paid player if Lillard is dealt, and Portland will have to figure out how to make him part of their rebuild.

This deal will likely look worse as Jerami Grant exits his prime. He turns 30 in March and will be 33 when deciding on his player option in 2027-28. It is not a fantastic place for the franchise to be.