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Blazers' Damian Lillard trade looks even better after massive Bucks overpay

Looks like Milwaukee isn't done making mistakes
Nov 30, 2025; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) shares a laugh before a game against the Oklahoma City Thunder at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images
Nov 30, 2025; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) shares a laugh before a game against the Oklahoma City Thunder at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images | IMAGN IMAGES via Reuters Connect

Any chance at a potential Gary Trent Jr. homecoming in Portland was shut down on Saturday, when the Milwaukee Bucks inked him to a massive overpay in the form of a four-year, $64 million deal.

Mind you, this was for someone coming off a season in which his -1.2 VORP was ninth-worst in the NBA. He averaged just 8.1 points per game while shooting an inefficient 38.7 percent from the field.

It's such a shocking decision that analysts have brought up their own theories regarding potential circumvention.

We liked the idea of Trent filling the Trail Blazers' final roster spot to add more shooting, but were thinking more along the lines of a minimum-salary deal. You know, not anywhere close to $16 million AAV.

Bucks' roster mistakes keep increasing the value of the picks owed to Portland

The Blazers have yet another potential free-agent target officially off the board, as their options continue to dwindle. The silver lining to this shocking Trent contract is that Portland is in a prime position to benefit from yet another mistake by Milwaukee's front office.

Thanks to the lopsided Damian Lillard deal, Portland still has control over Milwaukee's draft capital from 2028-30. That drastically increased in value with Giannis Antetokounmpo now in South Beach and the Bucks rebuilding around rookies Brayden Burries and Nate Ament.

Still, the assumption was that Milwaukee's future was on an upward trajectory as they embraced a post-Giannis era. But somehow, this front office has managed to mess up the roster so badly that they are still paying the price for the Giannis era.

Not only are they paying Trent an unjustifiable amount of money, but they also have Lillard still on the books after waiving and stretching his remaining $113 million salary over five years to clear space to sign Myles Turner. That's the largest waive and stretch in NBA history by a wide margin. Quite the all-in desperation move for a non-needle mover like Turner.

Between Trent at $15.2 million and Lillard at $21.3 million, these two players will account for over 22 percent of the Bucks' salary cap next season. Throw in Turner's $26.6 million into the equation, and that's 38 percent of the cap on an average starting center, a non-factor, and someone not even on the team.

Hard to fault Giannis for wanting to get out of that mess.

It's ironic because these moves were made in an attempt to convince Giannis to stay, but they ultimately dug Milwaukee into a hole so deep that the only solution was their loyal superstar finally requesting a trade. The Blazers' bet against the Bucks looks better than ever this summer, and this Trent news is just the cherry on top.

At this point, the only thing working against Portland's favor is the changing draft lottery odds in response to tanking. While that hurts their chances of coming away with a coveted draft prospect over these next few years, at least Milwaukee keeps shooting itself in the foot.

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