Blazers Could Play Shocking Role in Giannis Antetokounmpo Future

Hindsight is always 20/20 — though looking back at the 2023 trade between the Milwaukee Bucks and the Portland Trail Blazers, it appears as if the Blazers made out like bandits.

To appease Giannis Antetokounmpo moving forward, Milwaukee swung for the fences and acquired future Hall of Famer Damian Lillard. In return, the Blazers received Jrue Holiday (who they eventually dealt away), DeAndre Ayton, promising young player Toumani Camara, a Milwaukee 2029 unprotected first-round pick, and unprotected pick swap rights in 2028 and 2030.

Fast-forward two years, and this deal has aged terrifically for Portland. Camara has developed into a real piece moving forward. The draft pick capital is substantial. As for Milwaukee, Lillard tore his Achilles and won't be back until he's 36 years old.

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All of this makes the future moving forward wildly fascinating for both teams. If Milwaukee tries to bottom out by starting over and trading Antetokounmpo, Portland is the one that will benefit from that strategy. If they keep 'The Greek Freak' in Milwaukee, the team could be handcuffed in the purgatory of being too good to tank, yet too mediocre to contend.

Dan Favale of Rip City Project broke down this premise specifically. Portland essentially is holding all of the cards in this scenario.

"That is where the Blazers come into play. They have swap rights on the Bucks’ first-round pick in 2028, 2029, and 2030. The full details are a little more complex, but the overarching reality is, they have the ability to send out ownership of three out of Milwaukee’s next six drafts."

Blazer fans looking at the Bucks 2028, 29, and 30 picks right now pic.twitter.com/UEDLukn5K0
— Pinwheel Empire (@PinwheelEmpire) April 30, 2025

The Bucks are clearly in a tough spot. They could opt to recoup as many first-round picks as possible in an Antetokounmpo trade, knowing that their own picks — if valuable in any way — will be jettisoned to Portland.

At the same time, as Favale theorizes, could the Bucks try and reacquire those pick swaps in a deal for Antetokounmpo himself? At the very least, the Blazers have set themselves up quite nicely for the future as one of the potentially better young teams in the highly competitive Western Conference.

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For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.