When Damian Lillard requested a trade from the Portland Trail Blazers in 2023, his preferred landing spot was with the Miami Heat. That left Blazers general manager Joe Cronin in a tough spot. After all Dame's done for the franchise, would Cronin give him exactly what he wanted, or would he do what's in the best interest of the Blazers roster going forward?
Of course, the Blazers ultimately sent Lillard to Milwaukee instead of Miami, netting a major haul in the process. As part of the three-team blockbuster that included the Phoenix Suns, Portland received Deandre Ayton, building block Toumani Camara, Jrue Holiday, a 2029-first round pick, and two first-round swaps (2028 and 2030).
At the time, it appeared to be a win-win deal, as Cronin balanced getting a great return to help jumpstart Portland's rebuild while giving Lillard that realistic shot at a championship that led to the trade request in the first place.
In retrospect, it turned out to be more lopsided in the Blazers' favor, as the Dame-Giannis pairing surprisingly resulted in consecutive first-round playoff exits. While we wish that situation had worked out better for Lillard, the Bucks' all-in move backfiring benefited the Blazers to a greater extent than anyone initially anticipated.
Blazers' Damian Lillard trade keeps getting better
The potential Miami package wasn't necessarily a bad route to take. Nikola Jovic has potential at 22 years old, Jaime Jaquez Jr. is having a career year, and Tyler Herro is an All-Star who would've solved a lot of Portland's floor spacing problems. Still, that's nothing compared to what Cronin managed to pull off with Milwaukee.
In some ways, the Blazers did grant Lillard one wish at the expense of refusing another. Thanks to the lopsided deal, they were able to finally surround him with the pieces he always wanted during his first stint in Portland. It's a roundabout way, and shocking that they somehow have Holiday and Lillard both on the roster just two years later. But everything aligned perfectly for the Blazers.
A Dame return felt inevitable at some point in his career, but many expected it would be further down the road. The Bucks' desperate decision to waive and stretch Lillard to sign Myles Turner as a last-ditch effort to keep Giannis Antetokounmpo around actually benefited Portland twice. Lillard was able to return home, where he belongs, while the Bucks continue to lose leverage in ways to upgrade the roster and keep Giannis around. The worse Milwaukee gets, the more valuable that draft capital becomes; this trade is already a win for Portland, and those picks haven't even been conveyed yet!
The Blazers still need more star power to compete out west, but those picks could be their best bet to achieve that, whether through the draft or by trading for another established player -- potentially as a facilitator wherever Giannis lands.
Many point to the Deni Avdija trade as the defining move of the Cronin era and as the deal that boosted Portland's rebuilding ceiling, but it's quietly the Lillard trade that made all of this possible in the first place.
And the fact that Lillard returned to Portland after being waived by Milwaukee when he could've gone anywhere, shows that this ultimately turned out to be in the best interest of both Dame and the Blazers.