The Milwaukee Bucks are off to a predictably slow start to the season. They currently sit at 1-6, which could easily become 1-7 on Wednesday as they enter their road matchup against the Boston Celtics as heavy underdogs.
That should be a common theme this season in life post Giannis Antetokounmpo. Fortunately, the Portland Trail Blazers are set to benefit from Milwaukee's downfall thanks to the Damian Lillard deal.
The trade has come full circle, with Lillard back in Portland after just two seasons in Milwaukee. Even Lillard has said being traded away set up the Blazers to build the team he's always wanted in Portland. The Blazers are already winners in this trade with the Bucks and haven't even cashed in on the most valuable assets: future draft picks that keep growing in value.
Bucks picks look even more valuable with post-Giannis struggles
As part of that blockbuster three-team deal that also involved the Phoenix Suns, Portland received Jrue Holiday, Deandre Ayton, Toumani Camara, a 2029 unprotected first-round pick (via Milwaukee), and 2028/2030 first-round pick swaps (via Milwaukee).
This deal turned out to be a Trojan horse, sabotaging the Bucks from the inside. The Dame-Giannis pairing didn't fit as well as the Bucks hoped, partly due to untimely injuries that contributed to consecutive first-round playoff exits.
The Lillard trade was an aggressive move to win another ring with Giannis, but it backfired. But where Milwaukee really went wrong was doubling down on that decision. They kept digging themselves into a deeper hole in an attempt to keep Antetokounmpo content, and it ultimately pushed him further out the door.
The Kyle Kuzma deal with the Washington Wizards is one example, but the most head-scratching and notable move was waiving and stretching Lillard to clear space to sign Myles Turner. That was never going to be the needle mover this struggling Bucks roster needed. It's a decision that will haunt them for years to come, as they now have a dead cap hit of about $22.6 million annually after stretching Lillard's remaining $113 million over five years.
Damian Lillard trade continues to raise Portland's ceiling
The Bucks do have at least a few pieces to help initiate a rebuild without having most of their picks, whether it's Brayden Burries, Kel'el Ware, Ryan Rollins, Kasparas Jakucionis, or Nate Ament. While that's at least a young core, there's no true star to get this team back to relevance anytime soon. Ament has intriguing upside but also seems like a multi-year project, and that timeline bodes well for Portland, as these picks will convey before Milwaukee is ready to win again.
The flattened lottery odds in response to teams tanking do somewhat hurt the value of these picks that the Blazers stole in the Lillard trade. That said, they remain some of the most valuable assets in the league and could ultimately become the piece that puts the Blazers into that tier of contenders.
The Blazers and Bucks are off to opposite starts to the season, but you still get the sense that Portland is a piece or two away from truly being in that tier of Western Conference juggernauts like the San Antonio Spurs or Oklahoma City Thunder.
Blazers GM Joe Cronin had the option to package some of the Bucks' draft capital to make a splash this offseason, but he managed to add star power in Ja Morant without attaching any picks. With these bold trades paying off in Portland's rebuild and Cronin continuing to build the roster without sacrificing any Bucks draft capital, they'll be in a great position going forward.
Giannis trade rumors spiraling last year already hinted at this trade paying off for the Blazers. But now that he’s finally out of Milwaukee and the Bucks are struggling to start the season without him, this Lillard trade is starting to look like the one that will get the Blazers over the top.
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