If Giannis Antetokounmpo lands in Portland via trade this coming offseason, there's a very strong chance he re-signs with them. Because there's a very specific thing they can offer the Greek Freak that no other team can: a chance to team up once more with the two best point guards he's ever had in his career.
That's according to draft guru and The Athletic writer Sam Vecenie on the latest episode of the Game Theory podcast. And it's certainly interesting to think about, considering the Portland Trail Blazers have not been shy about their serious interest in acquiring the seemingly disgruntled Giannis Antetokounmpo from the Milwaukee Bucks.
"Do you think there's any way Gianns would re-sign in Portland with this group? Given they'd be able to retain Jrue Holiday and Damian Lillard, both guards that he really likes," Vecenie asked on the podcast. "He played with both of them, but does he fit with Deni Avdija is a whole other question."
The Damian Lillard era was one of their worst mistakes because it sold the farm for a few underwhelming years of a supposed super duo. But there's a path for Milwaukee to get their picks back if they want them.
There's a world where Giannis re-signs in Portland if he ever lands there
This is where the Giannis to Portland conversation becomes very interesting.
Giannis Antetokounmpo has never in his career played with point guards better than the likes of Jrue Holiday, with whom he won a championship, and Damian Lillard. It's even been reported that Giannis even once reached out to Holiday sometime this season to express how much he missed playing with him. That's a different kind of respect for Holiday, who was traded to Portland in order to land Lillard.
So there's a case to keep Giannis in town if they land him, which means there is definitely incentive for the Blazers to go after him. But what does this mean for the Bucks?
Portland still controls Milwaukee's first-round draft capital in 2028, 2029, and 2030 -- all stipulated by the original Damian Lillard trade. Those picks have been hanging over the Bucks' rebuild like a storm cloud. You can't truly start over when three of your future first-rounders belong to someone else. A Giannis deal with Portland is the one scenario where Milwaukee could conceivably trade its franchise player and get those picks back in the same transaction.
That means that choosing the Blazers as a trade partner would see them recovering from the Lillard mistake in one move.
A potential trade package could start with Shaedon Sharpe, Milwaukee's draft assets controlled by Portland, and maybe Jerami Grant to help match salaries. They could sweeten the pot too with additional pieces like Scoot Henderson or Orlando's unprotected 2028 first-round pick also on the table. That's a real offer.
Sharpe is 23 years old and one of the more explosive young wings in the league. Pairing him with AJ Green, Ryan Rollins, the young pieces Milwaukee suddenly found themselves with this year, and whatever else Milwaukee builds around in this upcoming draft gives the Bucks something they haven't had in years: a genuine core with actual draft capital behind it. That jumpstarts a rebuild basically instantly.
Would Giannis fit with the Blazers even with his former teammates?
Of course, there are still very real fit concerns that the Blazers will have to reckon with. It's hard, for instance, to feel enthusiastic about the prospect of pairing Giannis' ball-dominance and downhill pressure with the ball-dominance and downhill pressure of a guy like Deni Avdija, assuming he isn't part of the original trade package to begin with.
There's also been reporting recently that Giannis Antetokounmpo would rather remain in the East, perhaps to stay competitive and avoid the battles between the Oklahoma City Thunder and the San Antonio Spurs.
But Giannis Antetokounmpo holds both of his former teammates in high regard. And having him alongside the two of them can help the Portland Trail Blazers contend for a title going forward if they decide that's where they are now.
For the Blazers, if one of the league's best is (ostensibly) available and you have the assets to go and get him, you make that move nine times out of ten. And if an opportunity to right your past wrongs presents itself, like it is now for Milwaukee, you take the chance every time, too.
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