Jerami Grant's four-year contract with the Portland Trail Blazers has stirred some debate, especially considering the team's current rebuilding phase. At 30 years old, Grant is a valuable forward, but there's growing speculation that he may be traded before his contract expires. Despite this, the Blazers aren't in a rush to deal him. However, Bleacher Report’s Eric Pincus has labeled Grant's deal as the most regrettable on Portland’s roster, due to its hefty size and the limitations imposed by the 2023 NBA collective bargaining agreement (CBA).

Originally, Grant was re-signed with the expectation that he'd play alongside Damian Lillard. However, Lillard’s trade request shortly after Grant's extension shifted Portland’s plans. The team's salary cap situation is another factor, as they hover near the luxury-tax threshold for this year and the next. The Blazers might explore trading Grant before the deadline in February or by next July.