Strenuus
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One guy rates this as one of the worst re-signing deals:
The Portland Trail Blazers likely entered this offseason under the belief that any hope they had in keeping Damian Lillard happy began with bringing back Jerami Grant.
Well, as soon as the market opened, they routed every Brink's truck in the Pacific Northwest in Grant's direction and quickly got his commitment on a five-year, $160 million deal. And guess what happened? Lillard decided he was done with Portland, anyway.
Assuming the Blazers eventually grant Lillard's wish—at least by trading him somewhere, if not to his preferred destination of the Miami Heat—you'd think they would want to immediately pivot into a long-term rebuild around Scoot Henderson and Shaedon Sharpe. Portland insists that isn't the case, though.
"Our goal is to win to keep moving forward," Blazers general manager Joe Cronin told reporters. "We feel like our talent base is high."
Portland, for the record, went a combined 60-104 over the past two seasons, and that was with Lillard making 87 appearances. If Dame couldn't elevate this roster, who on earth is supposed to do that now? Good luck if the answer is Grant. He's a fine player, but the only team that leaned on him as a primary option was the Detroit Pistons, who went 43-111 during his two-year tenure.
He simply isn't worth this kind of coin—his 14.0 career player efficiency rating is actually a tick below league-average—and the only (relatively) reasonable rationale for the overpay was to keep Lillard happy. That obviously didn't happen, putting Portland in a wholly troublesome spot with Grant. At this pay rate, he might be impossible to trade for the next few seasons without incentivizing a team to take on his contract.
https://bleacherreport.com/articles/10083720-biggest-re-signing-mistakes-of-2023-nba-free-agency
What else were we going to do given the current climate of the team?