Three years ago, the Portland Trail Blazers were on their last attempts at building a contender around Damian Lillard by acquiring Jerami Grant, once simply a 3-and-D who transformed into a formidable wing scorer for the Detroit Pistons.
While he provided that scoring, improving his efficiency in the process (he went from 42.8 percent shooting in his two seasons in Detroit to 47.5 percent in his first season in Portland), injuries kept them from making the playoffs and Lillard was traded during the summer. The Blazers should've followed suit by shipping Grant away, and by not doing so, the window to maximize his value has passed.
As it stands, Grant's trade value is among the lowest in the league. He's a role player making over $32 million for the next three seasons, counting a $36 million player option for 2027-28. His decreased efficiency inside the arc (he shot 38.1 percent on 2-pointers this past season, a career-low) paired with his age (30 years old) doesn't give any hope for a turnaround. His 3-point shooting was still solid (36.5 percent), but nowhere near the level where that offsets the contract, especially given the restrictive new CBA. He's still a solid defender, but didn't have a significant impact in that.
Portland missed a golden opportunity to move him sooner
When Grant was coming off a second-straight 20+ point season last year, albeit in 54 games, the Blazers should've moved him. In July, they made the acquisition of Deni Avdija, who was coming off a 14.7 points per game season on 30 minutes per contest, and was primed for a larger role. Toumina Camara, a second-year wing, was also set for an increased role after a successful first season.
They both followed up on the promise, Avdija being Portland's third leading scorer, and Camara being of the best perimeter defenders in the NBA. While Greant was still a consistent piece of the rotation (he averaged 32.4 minutes, only one less than last season), his usage rate dropped from 25.7 percent to 19.4.
A lot of NBA teams would've wanted a wing that could impact on both sides to that degree. He could defend multiple positions, score in the mid-range, knock down catch-and-shoot 3s, and could get to the free throw line to the tune of five free throw attempts per game, a very good mark for a role player.
Wings of that caliber are the most coveted assets in the league. Some have went for a significant draft haul recently: Kyle Kuzma was traded to Milwaukee for a valuable 2028 draft pick, De'Andre Hunter was moved to Cleveland in exchange for five draft selections (two second-round picks and two swaps), Jae Crowder was traded to the Bucks for five second-round picks, and even Avdija himself was traded for three future draft picks and 'Bub' Carrington, a selection from this past draft.
Outside of how badly the Bucks have whiffed on adding role players to their core, it's clear Portland could've added a significant haul to their rebuild if they moved Grant in a timely manner. Instead, they missed out on accelerating their path to contention. They might make it even harder if they make the same mistake with Deandre Ayton.