Portland Trail Blazers general manager Joe Cronin rolled the dice when he sent Damian Lillard to the Milwaukee Bucks. A significant part of Portland's return in that blockbuster deal was Milwaukee's draft capital, meaning they were betting their future against a team with a top-three player in the world in Giannis Antetokounmpo.
Two seasons later, Cronin's decision looks much better. The Bucks have a flawed and aging roster that lacks flexibility, and they aren't able to build a contender around Giannis anytime soon. Every team in the league already knows this. But the Blazers are patiently waiting for Giannis to reach that same conclusion.
Blazers set to benefit from Bucks' flawed roster
The Blazers received an unprotected 2029 first-round pick and two first-round pick swaps (2028 and 2030) from the Bucks in the Lillard deal. The good news is that the value of those picks continues to increase regardless of whether Giannis decides to continue his Hall of Fame career in Milwaukee.
The Bucks waived and stretched Lillard, meaning they have dead money and will owe Lillard the remaining $103 million of his salary over the next five years (roughly $22.5Â million annually). Part of that myopic decision can be attributed to Milwaukee's desperation to compete next season and keep Giannis content. Lillard is expected to miss the entirety of the 2025-26 season after his Achilles tear, making it hard to convince Giannis to commit to an injured roster coming off two consecutive first-round playoff exits.
It's challenging to fault Milwaukee for doing something this offseason rather than just standing idle while Giannis weighs his options. However, the issue with their approach is that they signed Myles Turner. He's a solid starting center, but he isn't someone who will convince Giannis that this Bucks roster is any different than before. Milwaukee signed Turner to a four-year, $108.9 million deal. They now owe Turner and Lillard over a combined $200 million, making it much more challenging to upgrade their roster in the future.
The aging Bucks are running on fumes with no existing young core to improve this roster internally and limited future draft capital. The odds are they have enough to reach the postseason, but even the Washington Wizards with Giannis could make the playoffs in an injured Eastern Conference. The grim reality is that they are in basketball purgatory as a team that continues making win-now moves out of desperation but isn't a piece away from being a contender.
ESPN's Shams Charania reported on "Get Up" that "nothing is set in stone about whether Giannis Antetokounmpo will stay in Milwaukee or whether he will be leaving." The most important takeaway is the question Charania says Giannis has: "Can I win a championship with this roster?"
I don't know how you look at Milwaukee's roster and their moves this offseason and come to any conclusion other than no.