When Damian Lillard joined the Milwaukee Bucks, the goal was clear: win big with Giannis Antetokounmpo to bring the third ring home. But things fell apart quickly. Lillard dealt with nagging issues throughout the 2024-25 season before a serious groin injury finally shut him down. There was real concern he wouldn’t return for the entire 2025-26 campaign. Then came the shock. Instead of waiting, Milwaukee made a bold move: they waived him! Just like that, the Giannis-Dame pairing was over before it ever fully clicked, making the locker room and the Greek Freak digest the uneasy move. And now a former teammate has joined the debate, voicing his concern.
Even more surprising? The Bucks were creative with it, too; they stretched the remaining $113 million of Lillard’s deal over five years. That cleared over $22 million annually in cap space. With the money freed, Milwaukee signed center Myles Turner on a four-year, $107 million deal to reinforce their core. But Dame? He went right back to Portland, returning to a team that now features Jrue Holiday and Scoot Henderson. So, what does this all say about Milwaukee’s plan or lack of one?
“I didn’t see that coming,” Pat Beverley admitted. “You just heard one day small little somebody signing small somebody signing next thing you know Dame Lillard not even traded (but) waived!” That abrupt move hit harder because of what Lillard represented. He left Portland to chase a title, yet barely got a chance. Even Beverley, a straight-shooter, said, “If you asked me…did you think Damian Lillard was going to be waived this summer? Like I would have bet my bottom dollar that didn’t happen.” He still can’t get over Lillard getting waived.
So was Dame’s Milwaukee run a failure? “Him taking a chance and going to Milwaukee, you look back on it, did they underachieve or overachieve? You have to say under no? ” Beverley replied. They didn’t even make it past the first round in either season. And that raised questions about how Milwaukee built its roster. “My first lesson is that it is very hard to win with one-position defenders,” said Adam Ferrone, pointing to Lillard’s defensive limitations despite his offensive genius. He added, “So while you added another superstar next to Giannis, you don’t necessarily have as much versatility.”
Nov 12, 2022; Dallas, Texas, USA; Portland Trail Blazers guard Damian Lillard (0) checks the scoreboard during the second half of the game between the Dallas Mavericks and the Portland Trail Blazers at the American Airlines Center. Mandatory Credit: Jerome Miron-USA TODAY Sports
“You got to be able to guard,” Pat added. “You got to think, like, me and Dame might have the same amount of wins with Milwaukee in the playoffs.” Harsh? Maybe. But true. And while Lillard got paid and landed in a familiar spot, Beverley captured the lingering vibe: “I can’t wait till I play you m———–. Y’all got me f—-d up.” According to him, while Damian wouldn’t mind it considering the deal he got with the Blazers, there must be some lingering dissatisfaction inside. So the Bucks can expect some revenge when they inevitably cross paths this season.
How Giannis Antetokounmpo’s loyalty shifted the Knicks’ future and made Mikal Bridges $150 million richer
What happens when a team waits on a superstar who never comes? For the Knicks, it led to an unexpected $150 million decision. New York had quietly watched Giannis Antetokounmpo’s situation in Milwaukee, hoping for a crack to open. But once it became clear that Giannis wouldn’t ask out, they changed course. “The New York Knicks got intel that Giannis Antetokounmpo won’t request a trade from the Milwaukee Bucks before signing Mikal Bridges to an extension,” an NBA source told Hoops Wire.
Giannis’ decision not to leave didn’t just seal his own fate; it shaped someone else’s. The Knicks had real interest in acquiring the two-time MVP. But “all signs point toward Antetokounmpo remaining in Milwaukee.” With no blockbuster deal in reach, New York focused on keeping their core intact. Bridges, who was entering the final year of his deal, suddenly became a top priority. They offered him a four-year deal worth $150 million. That decision was focused on creating a stable future.
The question is, how does Bridges feel about being the Knicks’ Plan B? He got the biggest paycheck of his career, no doubt. But would that deal exist if Giannis Antetokounmpo had asked out? It’s hard to ignore that twist. “The Knicks would have pursued Giannis Antetokounmpo had the two-time MVP requested a trade from the Bucks.” But he didn’t. So Bridges cashed in. Whether that’s comforting or awkward depends on how you see it, grateful for the reward or aware of the circumstance.
Bridges has seen this before. He was part of the Kevin Durant trade in 2023 and knows what it feels like to be moved for a superstar. This time, he stayed, but only because the Knicks had to. That contract now comes with pressure. Can he live up to what could’ve been Giannis’ spot?
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