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Blazers continue to win Damian Lillard trade saga as former players flop

Years later, the Damian Lillard trade has aged almost impossibly well.
Apr 10, 2026; Portland, Oregon, USA;  Portland Trail Blazers guard Damian Lillard (0). Mandatory Credit: Jaime Valdez-Imagn Images
Apr 10, 2026; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0). Mandatory Credit: Jaime Valdez-Imagn Images | Jaime Valdez-Imagn Images

When the Portland Trail Blazers originally traded Damian Lillard in 2023, I was really bummed they had to give up Nassir Little. In hindsight, that was not a particularly important part of the deal.

The original trade — which sent Lillard to the Milwaukee Bucks — netted the Blazers Jrue Holiday, Toumani Camara, Deandre Ayton, an unprotected 2029 first-rounder, and a few pick swaps. Little, Jusuf Nurkic, and Keon Johnson went from Portland to Phoenix.

About 2.5 years later, Camara is an All-Defense wing and is locked down until 2030, Jrue Holiday was traded away and then acquired again, Damian Lillard is back, and the Blazers still have that Bucks pick, which is starting to look like it might be a massive asset. We don't need to talk about Deandre Ayton.

On the flipside, the guys Portland gave up are either end-of-bench guys or out of the league entirely. That's not a cause for celebration of course, but it's a stark difference from the pieces Portland got in return. Jusuf Nurkic actually started a lot of games for the Utah Jazz this season, but that isn't saying too much for a mega-tanking team. Little and Keon Johnson, meanwhile, are both out of the league entirely.

Blazers' Damian Lillard trade came at the exact right time

Even if Lillard didn't return on a three-year deal after being waived by the Milwaukee Bucks, this trade would be hugely successful for the Blazers. Camara and an unprotected first-rounder is already a good return, and then the Blazers effectively flipped Holiday to Boston for Malcolm Brogdon, Robert Williams III, and two first-round picks. One of those first-rounders is unprotected in 2029, and the other was paired with Brogdon in the Deni Avdija trade.

Then the Blazers got Holiday back from Boston for Anfernee Simons, who was on an expiring deal, meaning they basically got Deni Avdija, Robert Williams III, and a 2029 first-rounder for free. It's the trade that just keeps giving for the Blazers. Truly remarkable stuff from Joe Cronin, who should have a stranglehold on the GM job despite new ownership.

Lillard requesting a trade from the Blazers is the best thing that could have happened to the team. His wish was granted, and it allowed the Blazers to hit the reset button, focusing on a youth movement spearheaded by the guy they got in the Lillard deal and the guy they got in a deal that was only possible because of the Lillard deal. That works!

The rebuild is apparently over, according to Tom Dundon. I don't fully believe that. But after finishing above .500 and with a clear chance to be better next year, it's not a blasphemous statement from the new owner, and the only reason it's not egregious is because of how well the Damian Lillard trade worked out — and continues to work out — for this franchise.

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