The Portland Trail Blazers are quietly one of the most intriguing teams to watch as the NBA trade deadline approaches-not because of who they might trade, but because of who they’re tied to. Thanks to the Damian Lillard blockbuster, Portland holds a 2029 first-round pick from the Milwaukee Bucks, along with pick swaps in 2028 and 2030. And with the Bucks currently spiraling, those future assets are looking more valuable by the day.
Milwaukee is in a precarious spot. Despite the Eastern Conference being as wide open as it’s been in years, the Bucks are sitting at 18-25 and on the outside of the playoff picture.
That’s not just disappointing-it’s alarming. Especially when you have a generational star like Giannis Antetokounmpo on the roster, still in his prime, and visibly frustrated with the direction of the team.
Giannis has long maintained that he’s not the kind of player to force his way out. But Trail Blazers fans have seen this movie before.
Damian Lillard was the poster child for loyalty, sticking with Portland through years of playoff heartbreak and half-measure roster upgrades. Eventually, even Dame reached his breaking point.
And while Giannis’ resume and global profile may be even bigger, the echoes of Lillard’s situation are hard to ignore.
The Bucks, right now, are a team that smells of desperation. The kind of desperation that leads to short-sighted moves at the deadline, not long-term planning. Giannis recently made headlines by calling out “selfish” teammates after a blowout loss to the Thunder-comments that, while honest, only added fuel to the speculation surrounding his future.
Milwaukee’s front office is in a tight spot. They want to upgrade the roster.
They need to upgrade the roster. But thanks to the Lillard trade-which hasn’t delivered the results they hoped for-and a string of questionable decisions (like the Kyle Kuzma deal and waiving-and-stretching Lillard to bring in Myles Turner), their flexibility is basically gone.
They’re expected to make a move at the deadline. Frankly, they don’t have a choice.
But the options available aren’t exactly game-changers. According to reporting, the Bucks are eyeing players like Zach LaVine and Jerami Grant-talented, yes, but expensive and not necessarily the kind of pieces that vault you back into contention.
These are high-risk, high-cost moves that scream "we're out of ideas."
And that’s where Portland comes in.
The Trail Blazers don’t need to make a splash at this deadline to come out ahead. They just need to wait.
Every desperate move Milwaukee makes to try and salvage this season could end up increasing the value of those future picks Portland owns. If the Bucks flame out and Giannis decides this summer that he’s done wasting the back end of his prime, those 2028 and 2029 picks could be gold.
There’s also a scenario where Portland gets involved directly. If Giannis does eventually request a trade, the Blazers could position themselves as a facilitator-either to extract a valuable asset or to maximize the return on those picks they’re holding.
For now, Giannis is likely to stay put through the deadline. But the writing’s on the wall.
The Bucks are running out of moves, and the clock is ticking. Whether they can turn things around or not, the Trail Blazers are holding some of the most intriguing cards in the league’s long game.