You know the couple that is either going to get married and live happily ever after, or break up in the most destructive and explosive way possible? That's how it has felt watching the Milwaukee Bucks trying to please Giannis Antetokounmpo the past few years. Their first couple vacation in Phoenix went so well, it felt like they were on top of the world. But then things became stagnant for a few years and they tried to overcompensate with a last-second vacation to the Bay Area, and that ended in disaster, so now they're kind of in a waiting period which feels like it may culminate in an ultimatum. My metaphors were a little on the nose there, sorry.
Anyway, the NBA trade deadline is a little over five months from now. I don't think Giannis himself will be traded at the deadline — that would be pretty much the biggest in-season trade in NBA history — but I think once the deadline passes, we'll have a good idea of Giannis' future prospects, or lack thereof, in Milwaukee. If the Bucks roster looks similar or identical as it does right now... that's probably not a good sign.
While the trade deadline isn't some iron-clad, stone set deadline for the Bucks to improve around their megastar, it does feel like if this franchise enters next offseason with most of the same questions it entered this offseason with, then the big trade might actually go down before 2026-27.
This is mostly speculation — but we did get the first actual inkling of a potential trade from Giannis this summer when ESPN reported that he was going to "explore the best fits" for himself. That's basically a warning to Jon Horst and the rest of the front office: figure this out.
The Giannis rumors will continue to swirl if the Bucks disappoint
I want it on record that I hope the Bucks don't trade Giannis. He's established himself as a Bucks legend and watching an all-time talent stay in a small market his entire career is always satisfying. Plus, every Giannis trade "rumor" in the past five years have all been completely manufactured. He had plenty of chances to leave, and he didn't.
But now the rumblings are real, and the Bucks won't have an endless grace period. Signing Myles Turner was a great move, as was bringing back Gary Trent Jr. But these aren't the kind of moves that keep a two-time MVP around. I don't know what qualifies as that "kind of move," but the decision-makers better figure it out, because if we reach February of next year without seismic shifts to this roster, it will be pretty tough to justify that Milwaukee is the place for Giannis.