How the Portland Trail Blazers Could Land Giannis Antetokounmpo in a Blockbuster Trade
The Milwaukee Bucks face a ticking clock with their franchise player. Giannis Antetokounmpo will either accept or reject an extension this offseason. If it's the latter, the team needs a trade before he leaves in free agency after the 2026-27 season.
B/R recently examined the best realistic offers Milwaukee would expect from the Miami Heat and how the Golden State Warriors can pair Antetokounmpo with Steph Curry. The timing is tricky for the Bucks, since Antetokounmpo won't be eligible to extend until October 1, making their best window for a deal ahead of the NBA draft in June and the July free-agent period, when teams are at their most financially flexible.
Whatever he intends to do in October must be communicated clearly over the next two months. Meanwhile, if the Trail Blazers can sway the Bucks to send Antetokounmpo to Portland, the franchise would take a significant step forward after its recent first-round loss to the San Antonio Spurs.
Full Trade Scenario
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The Portland Trail Blazers receive: Giannis Antetokounmpo
The Milwaukee Bucks receive: Scoot Henderson, Shaedon Sharpe, Kris Murray, Matisse Thybulle (via sign-and-trade), 2028 first-rounder, 2029 1st rounder, 2030 reversal of prior first-round swap, 2031 protected first-rounder, $11.9 million trade exception (Antetokounmpo)
Trade Details
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By making the playoffs, the Trail Blazers will send their 2026 first-rounder (No. 15) to the Chicago Bulls. A deal can be consummated on July 6 after the NBA's annual moratorium.
Portland has several first-round swaps from Milwaukee from the 2023 Damian Lillard trade. Some of that is unwound, specifically, the 2030 swap is voided. In 2028, the Bucks owe the Washington Wizards the lower of their own pick and the Blazers' selection in a complex swap. That doesn't change, but Milwaukee now also receives the higher pick between the Bucks and the Blazers. Finally, the 2031 first-rounder has top-4 protection, otherwise it will be conveyed, unprotected, in 2032.
Avoiding a more complex trade to make salaries match for Antetokounmpo, the Bucks agree to take Thybulle via sign-and-trade on a three-year contract starting at $7.6 million. Only the first season would have guaranteed salary, assuming this is the best offer Thybulle can get in free agency. Given his injury history, that's a solid payday, even if Milwaukee cuts him after one season.
The Blazers are hard-capped at the first apron (projected at $209.1 million) by using the expanded traded player exception of their four outgoing players. So too are the Bucks, taking in Thybulle via sign-and-trade.
Why the Portland Trail Blazers Do It
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It's not complicated. The Blazers reunite Jrue Holiday and Damian Lillard with one of the NBA's best players.
Portland took a significant step forward this season, pushing to a winning record, a playoff berth through the play-in, and an initially competitive first-round series against the San Antonio Spurs. Still, the franchise has new ownership with Tom Dundon, bringing with him concerns on his willingness to spend (h/t Sean Highkin).
Dundon's cost-cutting measures behind the scenes may or may not impact what the team spends on its roster. Most NBA teams spend above the salary cap but below the luxury tax threshold, projected at $200.5 million next season. The Blazers can field a legitimate roster around Antetokounmpo with emerging star Deni Avdija, a healthy Damian Lillard, Jrue Holiday, Donovan Clingan, Toumani Camara, and Jerami Grant without spending into the tax.
If Dundon is willing to go above that line, the team should re-sign veteran center Robert Williams III, since rookie Yang Hansen isn't ready yet for a significant role. Portland can fill out the rest of its roster with minimum players.
The Trail Blazers would rely heavily on Holiday and Lillard, both of whom played with Antetokounmpo in Milwaukee, for recruitment. The cost for the former NBA Most Valuable Player would be promising young talent like Henderson, Sharpe, and Murray, along with multiple first-round draft picks.
In negotiation, Portland would try to reduce the number of picks or substitute Grant for Henderson, which could take the need for the Thybulle sign-and-trade off the table. Ultimately, the Blazers' offer must beat what teams like the Miami Heat are willing to give.
Why the Milwaukee Bucks Do It
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Assuming Antetokounmpo makes it clear he intends to move on, the team should canvass the league for the best possible offers. Antetokounmpo also has leverage in where he ends up. He's expected to opt out of his $62.8 million for 2027-28 and can use the threat of walking as an unrestricted free agent in 2027 should Milwaukee send him to an undesired location.
The Blazers and Bucks have worked together before, sending Lillard to Milwaukee in 2023 for Holiday. Soon after, Portland traded Holiday to Boston, but the Celtics sent him back before this season. Lillard rejoined the Blazers after Milwaukee waived and stretched his contract in July.
The Bucks still owe first-round draft compensation to the Blazers, some of which is recouped in this deal. Milwaukee lands Henderson, who has emerged this postseason in the losing effort to the Spurs. The former No. 3 pick (2023) is eligible for an extension this summer; otherwise, he'll be a restricted free agent in 2027.
Sharpe didn't play as large a role against the Spurs, but finished the 2025-26 regular season as a 20.8 points-per-game scorer. Murray, No. 23 in 2023, is still developing. Thybulle is a strong defender but a streaky shooter.
Milwaukee would need to highly value the combination of draft picks and talent to consider Portland's potential offer. It's substantial, competitive, and a viable path forward should the Bucks and Antetokounmpo decide it's time to go separate ways.
Email Eric Pincus at eric.pincus@gmail.com and follow him on X @EricPincus and Bluesky.
