It's certainly a pipe dream, but the Portland Trail Blazers now have all the pieces in place to try and make a blockbuster Giannis Antetokounmpo trade happen: projected cap space, teammate connections to Giannis, young assets, Milwaukee's future picks, and an ambitious new owner.
Even if he ultimately requests a trade, landing a top-three player in the world in Giannis will be highly challenging for a relatively small-market team like the Portland. However, the Blazers have key leverage in any trade negotiations that could set them apart from almost the entire league.
Thanks to the lopsided Damian Lillard deal, the Blazers have the Bucks' unprotected first-round pick in 2029 and swap rights in 2028 and 2030. If Giannis decides he wants out of Milwaukee, the Bucks would likely want those picks back, as not having them would defeat the purpose of a roster teardown and full-scale rebuild.
Before this surprising offseason, the Blazers made more sense as a team to facilitate any blockbuster Giannis trade. Portland could include Milwaukee's picks in a multi-team deal to get a rising star who better fits their rebuilding timeline than a 30-year-old Giannis. It would also cost less, allowing them to retain their young core.
But the Blazers' shocking offseason moves drastically altered their situation.
Portland has all the pieces required to pull off a blockbuster Giannis trade
Following the additions of aging stars Jrue Holiday and Damian Lillard, the Blazers are better equipped than ever to make an aggresive trade for a top-tier superstar to finally become contenders out west. Not to mention, Holiday and Lillard just so happen to be two of Giannis' former teammates.
This is unlikely to happen, especially anytime soon. It wouldn't be surprising if Giannis' loyalty to the Bucks franchise and city of Milwaukee prevails and he remains there for the 2025-26 season, especially with just two months until the start of the regular season. That could actually be a blessing in disguise for the Blazers.
ESPN projects Portland to have significant cap space in the 2026 offseason. Additionally, the Blazers franchise is set to be under new ownership by then, with March 31, 2026, being the target date for the closing sale.
Incoming owner Tom Dundon has a reputation for being ambitious because of his success with the NHL Carolina Hurricanes. As a source told Jason Quick of The Athletic, Dundon "brings a swagger" and "would have been trying to get Luka [Doncic]" last year.
Giannis could very well be the next franchise-altering superstar on the move, and it could be next summer if he realizes that Milwaukee isn't built to contend after what would be three consecutive underwhelming seasons at that point. Dundon may have a golden opportunity to make a home run swing for Giannis just months after officially owning the team.
Crazier things have happened in the ever-evolving NBA.