The Portland Trail Blazers may have lost out on a possible Gary Trent Jr. reunion, but the Milwaukee Bucks may have handed them something even better on Saturday: another reason to feel great about the Damian Lillard trade.
Trent agreed to a four-year, $64 million deal with Milwaukee, a number that stunned enough people to spark talk of possible circumvention. It was a huge payday for a player who finished last season with a -1.2 VORP, the ninth-worst mark in the NBA, and averaged 8.1 points per game while shooting 38.7 percent from the field.
Portland had been viewed as a possible landing spot for Trent, with the idea that he could fill the final roster spot and give the Blazers more shooting. But that was always going to be in the neighborhood of a minimum-salary deal, not something that lands at roughly $16 million a year.
Instead, the Bucks now have another questionable contract on their hands, and the ripple effect could help Portland. The Blazers still control Milwaukee’s draft capital from 2028 through 2030 because of the Lillard trade, and that stockpile has only grown more valuable as the Bucks have continued to stumble through their post-Giannis era.
Milwaukee’s future was supposed to be trending upward after moving on from Giannis Antetokounmpo, but the roster has somehow become even more expensive and more awkward. Trent’s deal is one part of that.
Lillard’s presence is another. The Bucks waived and stretched the remaining $113 million on Lillard’s contract over five years just to create the space to sign Myles Turner, a move that set an NBA record for the largest waive-and-stretch ever.
The financial picture is ugly. Trent will count for $15.2 million, Lillard for $21.3 million, and Turner for $26.6 million next season. Together, that’s 38 percent of the salary cap tied up in an average starting center, a player who is no longer on the roster, and a guard whose contract was stretched to make the whole thing work.
It’s a mess that makes Milwaukee’s decision-making look worse by the day, and it’s not hard to see why Giannis wanted out. The Bucks made these moves hoping to keep him, but instead they buried themselves so deep that the end result was their superstar finally asking for a trade.
For Portland, the big-picture concern is still the changing draft lottery odds that come with tanking. That does ding the Blazers’ chances of landing a premium prospect in the next few years. Even so, Milwaukee keeps giving them reasons to believe those 2028-30 picks could matter a lot.
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