The Portland Trail Blazers failed to surround Damian Lillard with the necessary pieces to contend during his first stint. That ultimately led to a trade request from their loyal superstar in 2023, when Portland embraced a rebuild around the top-ten picks Shaedon Sharpe and Scoot Henderson.
But should that decision to trade Lillard have actually come sooner? Bleacher Report's Dan Favale thinks so. The Blazers were among seven teams Favale lists for waiting too long to trade their stars, making the case that the heartbreaking Lillard breakup should've happened sooner.
Did the Blazers wait too long to trade Damian Lillard?
"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.
Lillard would end up being more negatively impacted by the continued relationship in Portland. He couldn't get over the hump with the Blazers' limited pieces surrounding him, using up the majority of his prime in the process.
He got a chance at that first ring with Giannis Antetokounmpo in Milwaukee, but that wasn't even Lillard's preferred landing spot despite his years of loyalty to the Blazers' franchise. That was a difficult decision for GM Joe Cronin to navigate in those Lillard trade talks. He had to balance giving Lillard a fair shot on a contending roster, while maximizing the best possible return for Portland.
Considering Antetokounmpo is no longer on the Bucks, Cronin's decision to send Lillard to Milwaukee instead of Miami or elsewhere looks better than ever.
Bucks' Damian Lillard package reshaped the Blazers' rebuild
It's almost single-handedly reshaped the Blazers' entire rebuild. They managed to come away with Deandre Ayton, Toumani Camara, Milwaukee's 2029 first-round pick, Milwaukee's swap rights in 2028 and 2030, and Jrue Holiday.
Of course, Holiday was flipped to the Celtics, helping them get over the championship hump. At the same time, Portland received Robert Williams III, Malcolm Brogdon, Boston's 2029 first-round pick, plus a 2024 first-round pick that was later packaged in the Deni Avdija steal with the Wizards.
Lillard unfortunately suffered two first-round playoff exits with the Bucks while he and Giannis weren't able to make it work, largely due to injuries and issues with the supporting cast. The low point was Lillard's brutal Achilles tear, which ultimately sidelined him for the entirety of the 2025-26 season.
The silver lining was that the injury led to the Bucks' (poor) decision to waive and stretch Lillard's salary to clear space to sign Myles Turner. That turned out to be a major win for Portland, who not only got Lillard back two seasons later but saw the value of those Bucks picks increase yet again as this team continued to sacrifice future flexibility in an attempt to keep Giannis around.
Damian Lillard trade has now come full circle for Portland
It's now managed to be a strange full-circle moment that somehow also included Portland reacquiring Jrue Holiday from the Celtics in a one-for-one swap of Anfernee Simons.
They now have arguably the most firepower Lillard has ever had in Portland, perhaps even giving him a puncher's chance at that ring he's always deserved.
At least the relationship between Lillard and the Blazers has been mended, and he's back in the Pacific Northwest where he belongs. But while he's still an NBA75 player, you can't help but wonder how Lillard's resume would look if he were less loyal, like ring-chasing stars around the league.
The Blazers were lucky to land such a loyal superstar to bring into their small-to-mid market; we've even seen this offseason that getting that level of talent to buy in is no easy feat. But seeing how the Lillard trade has played out, they were also lucky in terms of the timing to send him to the Bucks.
As Favale notes, this "doesn't excuse the process." The Blazers got bailed out by the Bucks' desperation, who are now even embracing a rebuild without control over their own picks.
It couldn't have played out better, showing how luck and loyalty both factor into rings. At least Lillard and the Blazers are aligned in that pursuit once again.
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