The centerpoint of the 2025-26 NBA season is nearing, and much like the leaves falling, the sunset creeping in earlier, and a brisk chill filling the air, another winter tradition is currently unfolding: Giannis Antetokounmpo’s loyalty to the Milwaukee Bucks is being questioned and tested by national media.
While an Eastern Conference player potentially asking out—and presumably being kept in the East—hardly amounts to news on this coast, the Portland Trail Blazers have quite a vested interest in how this drama unfolds. Lest we forget, two years ago, Damian Lillard was traded to the Bucks, and Portland received significant draft capital in return.
The Blazers own three future Milwaukee draft picks, none of which have yet to convey. The first and third of those three come in the form of pick swaps, in which the Blazers reserve the right to swap their draft pick with Milwaukee’s in 2028 and 2030. In 2029, the Blazers own Milwaukee’s draft pick outright.
Milwaukee also doesn’t fully own any of its own draft picks until the year 2031. That said, it is in Portland’s best interest for the Bucks to both get and remain bad through 2030, and Giannis asking out would unlock several juicy scenarios that might put the Blazers over the top.
Scenario 1: Milwaukee thinks it can immediately compete in a post-Giannis world
In this situation, Milwaukee decides to unload Giannis for a bevy of established players with some distant future compensation. The Bucks streamline the team payroll and put themselves in a much more flexible situation, similar to how Phoenix unloaded Kevin Durant for a pick and two younger, yet established, players with real value.
The best outcome here is the Bucks running into the same problems as before, struggling to tread water until ultimately throwing in the towel and relinquishing a high-level pick to the Blazers in 2028. Rebuilds typically take at least three seasons to see significant results, and putting off such a thing until Portland can sink its teeth into a couple of picks is ideal.
Scenario 2: The Bucks trade Giannis and start the rebuild immediately
While ripping the Band-Aid off and rebooting the franchise is likely the best path for the Bucks, it is by far the least enticing option for the Blazers. Beginning the rebuild immediately, armed with draft picks to replace their own, would give Milwaukee some runway to nullify the owed picks to all parties, including Portland.
As Milwaukee just signed division rival Myles Turner with presumed hopes to immediately compete, coupled with the CBA’s second apron hamstringing those teams that would dare to trade for a max player, this seems like the least likely option, but Giannis is good enough to force a championship-starved team’s hand.
Scenario 3: Milwaukee tries to make it work
This pathway is by far the most beneficial to Portland—when the first of Milwaukee’s picks conveys, Giannis will be 33 years old and on the wrong side of his prime. In 2028, the trio of Antetokounmpo, Turner, and Lillard will account for about 60% of the salary cap, further hampering flexibility. The media discourse is convinced that Giannis leaving is more of a “when” than an “if”, and the longer the Bucks push back the exit, the sweeter the two above scenarios become.
Ultimately, what the Bucks decide to do falls to Bucks General Manager Jon Horst and his view of where the franchise currently stands. That's why this scenario may not only be the best for Portland but also the most likely. NBA insider Jake Fischer recently reported on The Stein Line (subscription required) that Milwaukee is looking to go "big-game hunting" as a buyer at the deadline.
For Portland's sake, let's hope that's the case.