The Portland Trail Blazers bet against the Milwaukee Bucks when they acquired their future draft capital from the blockbuster Damian Lillard trade. Portland controls Milwaukee's draft from 2028-30, including a first-round pick in 2029 and swaps in 2028 and 2030. Those assets look better than ever with Giannis Antetokounmpo trade rumors intensifying leading up to the Feb. 5 deadline.
Milwaukee is seeking a combination of picks and young players in any return they get for Giannis. In other words, they want to rebuild. However, it's hard to do that without your own picks, giving Portland key leverage in the Giannis sweepstakes.
Should the Blazers cash in the Bucks picks?
Giannis isn't interested in heading to Portland, which should take that option off the table. Still, the Blazers could manage to come away with a key asset by facilitating a Giannis trade. Portland was already named a potential buyer at the deadline before this Giannis development, and now it has a clear pathway to acquire that piece to help get back to the postseason.
But given the increased value of those picks, Portland must be highly selective in who it decides to cash them in for. As Sam Vecenie recently noted on the Game Theory Podcast, it wouldn't be a bad idea to simply hold onto them.
"Again, I don't think it's a terrible idea here to short Milwaukee moving forward and being like 'let's keep these picks, these could be awesome,'" Vecenie said.
No matter what the Blazers ultimately decide to do, there will be some risk involved. They don't know how valuable those picks will become. But if the Blazers hold firm, it will reduce the value of the picks, since the Bucks will not have any incentive to be bad. It could be a top-five pick in the hands of Milwaukee but a 10-15 pick in the hands of Portland, for instance.
With so much tied to the future of a team that has no incentive to bottom out without benefiting from its own downfall, it wouldn't be a bad idea for the Blazers to sell high and diversify their investment.
“But from a trade perspective, 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, basically, [maybe] top 4 or 5 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,” Vecenie added.
One challenge lies in the teams that are favored to land Giannis: the Heat, Knicks, Warriors, and Timberwolves. Outside of Jaden McDaniels or maybe Karl-Anthony Towns, there aren't many intriguing assets that make sense for Portland to surrender that valuable draft capital for.
Mikal Bridges was a popular trade candidate in this scenario, but he doesn't make much sense. Portland must navigate this situation with one goal in mind: to raise its ceiling and eventually become a contender. Bridges isn't the needle mover they still need, and it's debatable if even McDaniels or Towns are, for that matter.
But general manager Joe Cronin has pulled off unexpected deals before, so perhaps Portland could leverage these picks to land someone who is currently overlooked.