Legendary podcaster/writer Bill Simmons recently highlighted a possibility that most Trail Blazers fans haven’t considered but is becoming more likely by the day: Giannis Antetokounmpo being traded to Portland.
Yes, you read that right. If your mind is blown, you might want to sit down for this one. If you’re skeptical, take a minute to give it a chance.
Bill Simmons ranks Blazers as second-place betting favorite to land Giannis Antetokounmpo
On an episode of The Bill Simmons Podcast, Simmons brought up Portland in a conversation with Zach Lowe, saying “the seatbelt is off with the Blazers the next three months” and that he’s “prepared for anything” with the team as they transition into a new ownership period. One thing he specifically noted is the likelihood of the team making a Giannis trade.
“If I had to bet on a Giannis team, I think I would bet on Portland in the number two spot behind the Knicks,” he said.
Now, that idea does feel a bit out of left field, but Simmons isn’t as delusional as he might sound.
The stars are aligning for a Giannis-to-Portland blockbuster
Antetokounmpo’s relationship with the Bucks is not in a good spot, nor is the Milwaukee organization as a whole. Recent reports from The Athletic’s Eric Nehm, ESPN’s Shams Charania, and others have brought disagreements, misalignments, and all kinds of other issues to light.
Things have been trending this way for a while, but it does feel like the long-anticipated Giannis trade may finally happen this summer. If this bombshell does enter the villa, Portland could attract him.
As a product of the Damian Lillard trade from 2023, the Blazers own multiple of Milwaukee’s first-round picks. If the Bucks are going to move on from the Greek Freak and enter a rebuild, they’d be borderline foolish not to try to reclaim the rights to their future in the draft.
That said, they’d almost certainly be calling Portland's phone, giving the Blazers a rare chance to acquire a generational player and make a massive leap in the standings in the 2026-27 season.
A few factors make this hypothetical trade far from a guarantee
It’s already been publicized that Giannis does not want to play in Portland, largely because of its market size and distance from Greece. That’s lame, because it’s a dope city, but that’s besides the point. Players of Antetokounmpo's caliber and influence don’t get traded where they don’t want to go.
Even if Antetokounmpo does have a change of heart, there’s a financial wrinkle that may ultimately shy both parties away. Giannis is extension-eligible next fall, and he probably wants to ink a new megadeal as soon as possible (the Bucks can offer him more money than any other team). If he signs an extension in October, though, he’ll be trade ineligible until the 2027 offseason. If the Blazers trade for him this summer, before the extension, then he’d enter free agency in 2027 and potentially walk away.
Giannis coming to Rip City is still a big hypothetical, but it’s very much in the cards, and it’ll be an interesting storyline to monitor in the coming months as the offseason approaches.