The Portland Trail Blazers spent years trying to make Damian Lillard’s first run in Portland work, and when it finally ended in 2023, the franchise pivoted into a rebuild built around Shaedon Sharpe and Scoot Henderson. But Bleacher Report’s Dan Favale argues the breakup should have come even earlier.
“Damian Lillard and the Portland Trail Blazers both suffered from their collective refusal to act. The ground shifted beneath them long before he signed a two-year, $112.6 million extension in 2022, but neither side seemed like they wanted to be the one to initiate breakup talks,” Favale writes.
That delay cost Lillard a big chunk of his prime. He kept trying to push a limited roster over the top in Portland, but the missing pieces never really arrived. By the time he finally got another chance at a title run, it came in Milwaukee alongside Giannis Antetokounmpo - and even that wasn’t Lillard’s preferred destination.
For general manager Joe Cronin, the trade talks had to thread a difficult needle: give Lillard a legitimate shot at winning while also bringing back the best possible haul for Portland. In hindsight, sending him to Milwaukee instead of Miami or another destination looks like a strong call, especially now that Antetokounmpo is no longer with the Bucks.
The package the Blazers landed has already shaped the next chapter of the franchise. Portland brought back Deandre Ayton, Toumani Camara, Milwaukee’s 2029 first-round pick, the Bucks’ swap rights in 2028 and 2030, and Jrue Holiday.
Holiday was later flipped to the Celtics, which helped Boston get over the championship hump. Portland then received Robert Williams III, Malcolm Brogdon, Boston’s 2029 first-round pick, and a 2024 first-round pick that was later included in the Deni Avdija deal with the Wizards.
Meanwhile, Lillard’s time in Milwaukee never fully clicked. The Bucks took two first-round playoff exits while injuries and roster issues kept the partnership from reaching its ceiling. The worst moment came when Lillard suffered a brutal Achilles tear that sidelined him for the entire 2025-26 season.
That injury ended up creating another twist that benefited Portland. Milwaukee waived and stretched Lillard’s salary to make room for Myles Turner, a move that turned into a major boost for the Blazers because Lillard returned to Portland two seasons later and the value of those Bucks picks kept rising as Milwaukee kept sacrificing future flexibility to stay in the mix around Giannis.
Now the whole thing has come back around in a way that almost feels surreal. Portland also reacquired Jrue Holiday from Boston in a one-for-one deal for Anfernee Simons.
The result is a roster that, according to the source article, gives Portland more firepower than Lillard ever had there before - maybe even enough to give him a real shot at the ring he has spent so long chasing.
The relationship between Lillard and the Blazers has been repaired, and he is back in the Pacific Northwest. Still, the story leaves room for the same question Favale raises: how different would Lillard’s resume look if he had been less loyal?
The Blazers were fortunate to land a superstar willing to stay in a small-to-mid market for as long as he did. They were also fortunate that the timing of the eventual trade worked out so well for them. As Favale puts it, that “doesn't excuse the process.”
In the end, Portland benefited from Milwaukee’s desperation, and the Bucks are now embracing a rebuild without control over their own picks. For the Blazers and Lillard, though, the path has looped back to the same goal.
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Damian Lillard is gearing up for an NBA return in the 2026-27 season after missing the previous year with a ruptured Achilles, and the comeback conversation in Portland is already taking shape. The Trail Blazers, who recently acquired Ja Morant, are expected to make Lillard a priority when he is ready to play again, a reminder that his place in the franchise picture remains a major part of the plan.
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More than a decade later, one old trade still sits at the center of how Portland thinks about its roster. In 2012, the Trail Blazers sent Gerald Wallace to the New Jersey Nets and brought back Sean Williams, Mehmet Okur, and the first-round pick that became Damian Lillard, the franchise-defining guard who went on to become the teams all-time leading scorer and carry Portland to multiple playoff appearances.
Lillards eventual trade to the Milwaukee Bucks in 2023 did not close the book on that deal so much as extend its reach. The Blazers have kept building around the assets and movement that followed, adding pieces such as Toumani Camara, Jrue Holiday, Malcolm Brogdon and Deni Avdija, along with future pick swaps that still shape what Portland can do next. [Read more 🡒]