The Portland Trail Blazers have quietly entered one of the NBA’s most high-stakes conversations - the future of Giannis Antetokounmpo. While most teams are circling around the idea of facilitating a deal to help Milwaukee regain control of its future draft picks, Portland is aiming higher.
They don't just want to be part of a Giannis trade. They want Giannis himself.
According to NBA insider Jake Fischer, the Blazers are actively trying to bring the two-time MVP to Portland to reunite him with his former teammate Damian Lillard. And this isn’t just front office smoke - Lillard is reportedly working behind the scenes to make it happen, pushing for a reunion with the Greek Freak in the Pacific Northwest.
This is where things get interesting. Portland’s leverage in this situation is real.
As part of the Damian Lillard trade, the Blazers now hold key Bucks draft picks from 2028 to 2030 - picks Milwaukee would love to get back if it ever decides to hit the reset button. If the Bucks do move Giannis, regaining control of their future would be a top priority, and Portland’s draft capital could be the key to unlocking that door.
Financially, a deal is also within reach. Giannis is earning $54.1 million this season, and the Blazers could get close to that number by moving Jerami Grant’s $32 million contract, along with a couple of mid-tier salaries. Names like Scoot Henderson, Robert Williams III, and Matisse Thybulle - all making between $10-13 million - could be included to balance the books.
From Milwaukee’s side, there’s some potential intrigue. Scoot Henderson, the No. 3 overall pick in the 2023 draft, still has star upside.
Williams and Thybulle are on expiring deals, offering flexibility. If the Bucks were to pivot toward a rebuild, this kind of package - young talent, expiring contracts, and control of their own draft future - could be appealing.
But here’s the catch: Giannis reportedly doesn’t want to come to Portland.
That’s the biggest hurdle in all of this. Portland checks none of the boxes Giannis is believed to value in a destination - it’s a small market, the weather isn’t exactly beachy, and it’s a long flight from Greece. Even with the pieces in place, convincing Giannis to buy into a move to the Pacific Northwest is the true challenge.
Still, the Blazers aren’t backing down. With the trade deadline just days away, they’re positioning themselves as a legitimate dark horse.
The connection between Dame and Giannis isn’t just a footnote - it’s a real factor. The two never quite found their rhythm in Milwaukee before Lillard was moved, and there’s a sense that they could have unfinished business together.
Giannis is under contract for next season and holds a player option for 2027-28, so even if Portland were to land him without a long-term commitment, they’d have a full season to make their pitch. That’s a gamble, no doubt - but it might be the kind of swing the Blazers have to take if they want to vault themselves into true contender status.
Opportunities to land a top-five player in the world don’t come around often. Portland has the assets.
They have the connection. Now, it’s about convincing Giannis that the Rose City could be the place to chase another championship - this time, with Dame by his side.