The Portland Trail Blazers made a long-term gamble when they dealt Damian Lillard to the Milwaukee Bucks, and now, that bet is starting to look pretty savvy. Portland owns the rights to Milwaukee’s draft from 2028 through 2030 - including a 2029 first-round pick and pick swaps in 2028 and 2030.
Back when the deal was made, those future picks were intriguing. Now, with Giannis Antetokounmpo trade rumors heating up ahead of the February 5 trade deadline, they might be golden.
Here’s the situation: Milwaukee, according to league chatter, is open to moving Giannis if the return includes a mix of draft picks and young talent. That’s the kind of package that screams “rebuild.”
But rebuilding without your own picks? That’s a tough sell - and that’s where Portland comes in.
The Blazers essentially hold the Bucks’ future in their hands. If Milwaukee trades Giannis and hits the reset button, Portland stands to benefit in a big way.
The worse the Bucks are in the coming years, the more valuable those picks become for the Blazers. So the question becomes: should Portland cash in now, or ride this out and hope those picks turn into premium lottery tickets?
Let’s be clear: Giannis isn’t heading to Portland. That’s not on the table.
But that doesn’t mean the Blazers can’t play a role in a potential deal. In fact, they might be one of the most important players in the Giannis sweepstakes - not as a destination, but as a facilitator.
Portland has already been floated as a potential buyer at the deadline, and this Giannis situation could open the door to a creative move. If they can use their control over the Bucks’ draft to insert themselves into a multi-team deal, they might be able to walk away with a high-level asset - the kind that could accelerate their return to playoff contention.
But here's the tricky part: those Milwaukee picks are gaining value by the day. If Giannis leaves and the Bucks tumble, those picks could end up in the top five.
That’s the kind of asset you don’t give up lightly. As analyst Sam Vecenie pointed out on the Game Theory Podcast, there’s a real case to be made for holding onto them.
“Again, I don't think it's a terrible idea here to short Milwaukee moving forward and be like, ‘let's keep these picks, these could be awesome,’” Vecenie said.
That’s the dilemma. If Portland holds onto the picks, they’re betting that Milwaukee’s post-Giannis era goes south - fast.
And let’s be honest, without their own picks to tank for, the Bucks don’t have much incentive to bottom out. That could limit just how far they fall.
A pick that could be top-five in Milwaukee’s hands might only land in the 10-15 range once it transfers to Portland.
So maybe this is the time to sell high. The picks are valuable now because of the uncertainty surrounding the Bucks.
If Portland waits too long and Milwaukee somehow stays competitive, the shine could wear off. Vecenie put it this way: “I don’t think Portland will ever have more leverage with those picks than they do right now unless those picks turn into top-3 picks… and that’s very possible, but you’re really running a risk on some level by hoping and guessing that that’s where those are going to be.”
Of course, even if Portland decides to move the picks, the return has to be right. And that’s where things get complicated.
The teams most often linked to Giannis - the Heat, Knicks, Warriors, and Timberwolves - don’t exactly have a treasure trove of assets that make sense for the Blazers. Outside of Jaden McDaniels or maybe Karl-Anthony Towns, there aren’t many players who would justify Portland giving up that kind of long-term value.
Mikal Bridges? He’s been floated as a possibility, but he doesn’t move the needle enough for a team trying to build toward real contention. Even McDaniels or Towns might not be the answer, depending on how Portland views their fit and ceiling.
That puts general manager Joe Cronin in a familiar position - navigating a high-stakes situation with limited clarity. But if there’s one thing we’ve learned from Cronin’s tenure, it’s that he’s not afraid to get creative. He’s pulled off surprise moves before, and if there’s a way to turn these picks into a foundational piece, he’ll find it.
For now, the Blazers are sitting on a potential goldmine. Whether they decide to cash in or hold tight will say a lot about how they view their timeline - and how much they believe in the value of a bet they made months ago.