Giannis Antetokounmpo didn’t re-sign with the Milwaukee Bucks to waste his prime on a team stuck in neutral. But here we are - the Bucks are 9-13, reeling from a brutal loss to the lowly Washington Wizards, and fans are calling for head coach Doc Rivers’ job. This isn’t the vision Giannis signed up for, and it’s becoming harder to ignore the reality: Milwaukee is spiraling, and the clock is ticking on one of the league’s most dominant superstars.
Let’s start with the obvious. Giannis is 30.
That’s not old by any stretch, but in NBA years - especially for a player who relies so heavily on athleticism - it’s the back half of the prime window. And right now, that window is being wasted.
The Bucks aren’t just underperforming; they’re sitting near the bottom of an Eastern Conference that’s been riddled with injuries and inconsistency across the board. If ever there was a year to stay afloat through adversity, this was it.
Instead, Milwaukee is sinking.
The front office tried to make moves to keep the Bucks competitive, but the results haven’t matched the ambition. The additions of Kyle Kuzma last season and Myles Turner over the summer were meant to give Giannis more support.
But neither move has shifted the balance of power in the East - or even kept Milwaukee in the mix. The roster is aging, the margins are thin, and the flexibility is gone.
The biggest blow, though, came with the stunning decision to waive and stretch Damian Lillard’s remaining $113 million salary over five years - the largest waive-and-stretch maneuver in NBA history. That move gives the Bucks some short-term breathing room, but it also leaves them paying for a player no longer on the roster through 2030. It’s the kind of financial commitment that can hamstring a franchise for years.
And while Milwaukee is left searching for answers, the Portland Trail Blazers are quietly sitting in a perfect position.
Remember, when the Blazers dealt Lillard to Milwaukee, they didn’t just move on from a franchise icon - they bet on the Bucks’ future. General manager Joe Cronin secured a 2029 first-round pick and two pick swaps in 2028 and 2030.
At the time, those were viewed as long-term assets with uncertain value. Now?
They’re looking like gold.
Portland has a young, ascending core and a clear direction. With Scoot Henderson developing, Shaedon Sharpe flashing star potential, and Deandre Ayton anchoring the frontcourt, the Blazers are building something sustainable. If they stay on this path, they could be back in the playoff mix just as those Bucks picks start to mature - right when Milwaukee could be bottoming out.
It’s a classic win-win scenario for Portland. If Milwaukee continues to slide, those pick swaps could net the Blazers premium draft positioning.
And if Giannis eventually decides he’s had enough and asks out? Portland might be holding the keys to the sweepstakes.
Now, let’s be clear - landing Giannis is a long shot. But it’s not completely out of the question.
Portland already added two of his former teammates in Jrue Holiday and Lillard (though Holiday has since moved on). If the Blazers were to package those Bucks picks with a player like Scoot Henderson, they’d have a compelling offer - especially if Giannis signals a preference for a specific destination.
Even if that dream never materializes, Portland’s position as a facilitator in any potential deal is a powerful one.
Bottom line: Milwaukee’s collapse is Portland’s gain. Whether it’s through those future picks, a surprise trade opportunity, or simply the ability to capitalize on a franchise in flux, the Blazers are poised to benefit in a major way. For a team that just a year ago was facing the end of an era, that’s a pretty remarkable turnaround.
As for Giannis, the loyalty is admirable. He stayed when others might have walked.
But loyalty only goes so far when the wins dry up and the path forward gets murky. The Bucks have some serious soul-searching to do - because right now, the future they mortgaged to chase a title is looking a lot brighter in Portland than it is in Milwaukee.