The notification hit phones like a thunderbolt on that September afternoon in 2023. Damian Lillard was going to Milwaukee. After months of "Dame Time" posturing and a very public standoff with the Portland Trail Blazers, the superstar guard wasn't headed to his preferred destination in Miami. Instead, he was joining forces with Giannis Antetokounmpo.
It felt like a cheat code. Honestly, most of us thought the Eastern Conference was over before it started. You had the most dominant interior force in the league pairing up with arguably the most lethal deep-range closer in basketball history.
But looking back from 2026, that original Bucks Damian Lillard announcement feels more like a cautionary tale than a championship blueprint. What was supposed to be a dynasty-altering blockbuster ended in a way nobody predicted: a "waive and stretch" and a quiet return to the Pacific Northwest.
The Trade That Cost Everything
To understand why the announcement was such a big deal, you have to remember what Milwaukee gave up. This wasn't a "buy low" situation. Jon Horst, the Bucks GM, pushed every single chip into the middle of the table.
They sent out Jrue Holiday—the heartbeat of their 2021 championship defense—along with Grayson Allen and an unprotected 2029 first-round pick. They also gave Portland pick swap rights for 2028 and 2030. Essentially, the Bucks traded their past (Holiday) and their entire future for a window they thought would stay open forever.
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The immediate reaction was pure euphoria in the 414. Giannis was happy. The fans were electric. Even the rival GMs in the East were scrambling. But the cracks formed faster than anyone expected.
While Lillard was putting up 24.1 points per game, the defensive identity of the team evaporated. Holiday's absence was a gaping wound. Then came the coaching carousel—Adrian Griffin out, Doc Rivers in—and the vibe just never got right.
Why the Bucks Waived Damian Lillard
If you told a Bucks fan in 2023 that the team would eventually waive Lillard just to clear cap space, they would have called you insane. Yet, that's exactly what happened in July 2025.
The "announcement" that truly broke the fanbase wasn't the trade—it was the news that the Bucks were waiving and stretching the remaining $113 million on Lillard’s contract. This is virtually unheard of for a player of his stature.
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- The Injury Factor: A torn left Achilles tendon during the 2025 playoffs against the Indiana Pacers was the final straw.
- The Financial Logjam: With Lillard sidelined and the team facing massive luxury tax penalties, the front office made a cold, hard business decision.
- The Myles Turner Move: Milwaukee needed a defensive reset. To sign Myles Turner and retool around Giannis, they had to get Lillard’s massive salary off the immediate books.
The math is brutal. Because they used the "stretch provision," the Bucks are now paying Lillard roughly $20.2 million per year through 2030 just to not play for them. It is arguably the most expensive "divorce" in NBA history.
The Storybook Return Nobody Saw Coming
While Milwaukee was left picking up the pieces, Lillard did something even more shocking. He went home.
Shortly after being waived, the Bucks Damian Lillard announcement was superseded by news from Portland. Dame signed a three-year, $42 million deal to return to the Trail Blazers. Because he was already getting $20 million a year from Milwaukee’s "dead money," he was able to sign a "team-friendly" deal with Portland.
Basically, the Bucks are subsidizing Lillard’s second act in Portland. It’s a bizarre reality where a small-market team like Milwaukee is paying a superstar to help a different small-market team rebuild.
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Where the Bucks Stand Today (January 2026)
Life after Dame has been rough. As of mid-January 2026, the Bucks are sitting at 17-23, hovering near the bottom of the Eastern Conference standings.
The defense is better with Myles Turner, sure, but the "fear factor" is gone. Teams don't stay awake at night worrying about the Bucks' perimeter shooting anymore. There’s even talk now about the team being "desperate" enough to trade for someone like Ja Morant, simply because the Lillard experiment left them with so little offensive creation.
It’s a stark contrast to the 2023 announcement that promised a "new era of greatness."
Actionable Takeaways for Following NBA Transactions
If you're tracking these kinds of blockbuster moves, here is what we've learned from the Lillard-Milwaukee saga:
- Look at the "Hidden" Costs: When a trade involves unprotected picks five years out (like 2029), the "winner" of the trade can't be decided for half a decade. Portland is currently sitting on a goldmine because the Bucks are struggling.
- The "Waive and Stretch" is a Last Resort: If you see your team using this on a superstar, it’s a sign of total organizational desperation. It clears cap space today but poisons the well for the next five years.
- Chemistry Over Stars: On paper, Dame and Giannis were perfect. In reality, the lack of a defensive point of attack (which Jrue Holiday provided) mattered more than the extra 10 points Lillard brought to the table.
The original Lillard announcement felt like a beginning. In hindsight, it was the start of a very expensive end. For the Bucks, the goal now is surviving the financial fallout while trying to keep Giannis convinced that Milwaukee is still the place to be.
Next Steps for Bucks Fans: Keep a close eye on the February trade deadline. With the team sitting at 11th in the East, the front office is likely to dangle their 2031 first-round pick. Whether they chase a guard like Morant or look for more depth, the ghost of the Lillard contract will continue to haunt their cap sheet for years.