When Damian Lillard’s Achilles tendon ruptured on April 27, his career was in a precarious place. It was reasonable to predict that the injury would mark the end of the Milwaukee Bucks as we’ve known them, that they’d be forced to trade franchise player Giannis Antetokounmpo, and that Lillard, after spending the 2025-26 season rehabilitating, would return to a team that had no use for him. If they were to trade Lillard at some point before his contract was set to expire in 2027, there would be no telling where he’d land up.
Eighty-one days later, Lillard might be the biggest winner of the offseason.
Because the Bucks decided to waive Lillard and use the stretch provision to open up cap space, Lillard had the chance to go wherever he wanted. An unrestricted free agent for the first time in his career, he chose to go home. He’ll join the Portland Trail Blazers on a three-year, $42 million deal, according to ESPN’s Shams Charania.
The Blazers will pay Lillard $14.1 million (i.e. the full midlevel exception) next season despite the fact that he’s unlikely to appear in a single game. He reportedly planned to do his rehab in Portland regardless of where he signed, so he could be with his kids. If he ever leaves again, it will be on his terms: Lillard has a no-trade clause, per ESPN, as well as a player option on the third year of the contract.
If he plays at an elite level when he returns and/or wants to chase a championship elsewhere, he can hit free agency in the summer of 2027, just like he would have if the Bucks had never waived him. On top of all that, Milwaukee will pay him $22.5 million annually for the next five years.
Damian Lillard returning to Trail Blazers: Nine-time All-Star reuniting with Portland on $42M deal, per report
Jasmyn Wimbish
This is an unexpected homecoming that has the potential to pay off beautifully for both parties. I have questions about the Blazers’ allocation of resources — the 21-year-old Scoot Henderson and 22-year-old Shaedon Sharpe were supposed to be the backcourt of the future, and now there are two 35-year-old former All-Star guards in the picture? — but I have no qualms whatsoever about Lillard’s side of the reunion story. No other team could have legally offered him a no-trade clause, and it’s hard to imagine any of his other suitors offering the full midlevel to get healthy in the Pacific Northwest.
Two years ago, when it became clear that Portland wasn’t going to send him to the Miami Heat, Lillard tried to walk back his trade request. That didn’t work. But when he returned to the Moda Center with the Bucks, he got a hero’s welcome: multiple video tributes and a standing ovation during player introductions that lasted more than a minute. He can’t be a one-team guy anymore, but, if he finishes his career in Rip City, his two years in Milwaukee will go down like Michael Jordan’s two years in Washington: Largely unremarked upon, apart from a joke here and there and, occasionally, someone insisting that he was more productive at the time than anyone cares to remember.
It will be some time before Lillard pulls up from the logo in a Blazers uniform again, and it’s unclear how much momentum the franchise will build between now and then (and who will own it). His return, though, will be a monumental moment in Portland. It already is.
Lillard can’t undo his devastating injury, nor can he get a mulligan on the whole Milwaukee experience, but this is the next best thing.
