The path Giannis Antetokounmpo takes this offseason could set off a major trade ripple, and Portland may end up helping decide where he plays next. The two main destinations now appear to be Boston and Miami, not Portland, even though the Trail Blazers have shown strong interest in him and hold Milwaukee's draft picks from 2028 through 2030.
If the Bucks choose a rebuild, those picks could become very valuable for Milwaukee, especially if Portland sends back young players and future flexibility. The Blazers also have their own young core, including Shaedon Sharpe, who averaged 20.8 points this season and showed he can score consistently, though his role overlaps somewhat with Deni Avdija and Scoot Henderson.
The most realistic big-name target for Portland is Jayson Brown of Boston. The article says Brown would fit well next to Avdija and Damian Lillard, giving Portland a wing who can shoot, create offense and defend at a high level. Together, the three could push the team toward 50 wins and contender status, while Boston would get Antetokounmpo after a season in which it lost 3:1.
The problem is cost. Brown is under one of the NBA's biggest contracts, with more than $60 million due in both 2027/28 and 2028/29. Portland would likely have to give up Jerami Grant and Sharpe, but that would still leave Brown far more expensive than Sharpe in the later years. Avdija's deal ends in 2027/28, and if Portland extends him it would already be paying heavily in the first two seasons, while also having to account for Donovan Clingan and Henderson. That could severely limit the Blazers' financial flexibility, even if Brown is considered the best talent available.
Miami's offer, which includes Tyler Herro, Jaime Jaquez, Kel'el Ware and draft picks, is described as less compelling for Portland. Minnesota has also entered the picture, with a possible package involving Julius Randle and Naz Reid if Antetokounmpo wants to play with Anthony Edwards. Randle's deal also runs through 2027/28, but the article concludes that for Portland, Brown remains the best option on the table.
