
via Getty
DENVER, CO – MAY 12: Damian Lillard (0) of the Portland Trail Blazers prepares to resume action against the Denver Nuggets during the second quarter on Sunday, May 12, 2019. The Denver Nuggets versus the Portland Trail Blazers in game seven of the teams’ second round NBA playoff series at the Pepsi Center in Denver. (Photo by AAron Ontiveroz/MediaNews Group/The Denver Post via Getty Images)

via Getty
DENVER, CO – MAY 12: Damian Lillard (0) of the Portland Trail Blazers prepares to resume action against the Denver Nuggets during the second quarter on Sunday, May 12, 2019. The Denver Nuggets versus the Portland Trail Blazers in game seven of the teams’ second round NBA playoff series at the Pepsi Center in Denver. (Photo by AAron Ontiveroz/MediaNews Group/The Denver Post via Getty Images)
“Damian Lillard Will Miss…” The phrase strikes hard if you associate with the Milwaukee Bucks. Until late in the passing season, from GM down to coaching and fans, every Bucks loyalist prayed Dame shouldn’t miss a game because hopes for the title were tied to him, too. But Lillard tore his left Achilles tendon during a first-round NBA playoff series against the Indiana Pacers, who went on to play the finals, forcing the management to say, Lillard, Thank You for your services. But in the world of sports, rare chemistry between superstars goes beyond the locker room. And for Damian Lillard, his short but memorable run with Giannis Antetokounmpo in Milwaukee fits that bill perfectly.
When Dame joined the Milwaukee Bucks just two seasons ago, the entire league took notice. It was a blockbuster move, one meant to shake the East and elevate the Bucks into title favorites, and it was promising this season. Fans were electric with hope, expecting Dame and Giannis to light up the court like few duos ever had. But the hype soon gave way to reality. And with a season of unavailability, the front office made hard decisions to fix the roster as financial cracks began to form. And of all fears, the one that hit a chord was what happens to the duo of Lillard and Greek Freak?
Cutting ties with Lillard and taking on more than $22 million in dead cap space was big, even if that meant a star-studded pairing ended. The numbers might show a brief tenure, but there was something special in those 116 regular-season games to tag it as a pair. Injuries and roster instability kept Lillard and Giannis from fully blooming, but the sparks were undeniable—especially early on. In fact, the Bucks’ offense surged during their first 10 games together, posting numbers the franchise hadn’t touched in six years. That chemistry, however, was fleeting, and we aren’t assuming. During a recent heart-to-heart with the Journal Sentinel, Lillard didn’t hold back on how it felt being beside Giannis.
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“It was a great experience. I think more than anything, just the luxury of playing with a player as great as him. And having those nights where I can show up and he’s gonna carry a lot of the load, and he might be feeling it that night, and we can win a game with me scoring 12 points. So just the luxury of having him on your team was a special thing.” Lillard couldn’t help but share his respect playing beside the No. 34. But “more than no matter what happens I’m playing with a dude where we can combine and beat anybody,” the Blazers No. 0 shared what he will miss next.
He went on to say, “But as a tandem with him, I felt like we can go and win it all with the two of us. We can just go on a run and just dominate. I’m not sure I’ll ever have that experience again. But it was great playing with him. It was truly a pleasure and a luxury to play with a guy that dominant and also a guy who cares that much. I think that was something I really appreciated,” he shared, a line soaked in nostalgia. Truly, the Bucks side felt a bit different when the two hit the court, even if it meant a season and a half.
For Dame, it wasn’t just about the wins—it was about the belief that on any given night, the two of them could tilt the entire league. Even when he stumbled, Lillard found peace in knowing Giannis was there to pick up the slack and finish the job. But the Bucks had their own timeline to follow. Faced with hard decisions, the front office shocked many by letting Lillard go barely two years in. The move left fans scratching their heads, especially considering the $22.5 million penalty they’d now carry annually for the next five seasons.

USA Today via Reuters
Feb 15, 2024; Memphis, Tennessee, USA; Milwaukee Bucks guard Damian Lillard (0) and Milwaukee Bucks forward Giannis Antetokounmpo (34) react during the second half against the Memphis Grizzlies at FedExForum. Mandatory Credit: Petre Thomas-USA TODAY Sports
One executive opened up about the emotional weight behind it: “That was really, really hard. Dame is such a great player and we’re all thrilled that he landed back home in Portland… But when you have Giannis, you have to be willing to do what it takes to win and maximize your time with him.” The Milwaukee Bucks wasn’t just tweaking the roster. They were going all-in, hoping Myles Turner could offer the impact they needed now, even at the cost of future flexibility. And for Damian Lillard? That unique synergy with Giannis Antetokounmpo, that unspoken rhythm, they built might just be the one thing he won’t find again, no matter where he plays next.
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What’s your perspective on:
Could Lillard and Giannis have been the NBA's most dominant duo if given more time?
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Damian Lillard answers questions about his time in the Milwaukee Bucks
Damian Lillard’s conversation with the Journal Sentinel naturally drifted toward what fans have been wondering for a while — did his stint in Milwaukee feel incomplete? With injuries disrupting back-to-back playoff runs, it’s a fair question. But Dame didn’t seem rattled by it. In fact, his response was as calm and collected as his on-court demeanor.
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“I think it’s just basketball. It don’t feel incomplete to me. I just feel, just basketball. I think you gotta be a little bit lucky to win big. You gotta be healthy and you gotta be playing your best at the right time and I think we just had bad luck,” he said. It’s easy to forget amid all the noise that Damian Lillard and the Bucks spent most of last season sitting comfortably in the top 6, only dropping out of the season in the playoffs. But even after sitting out for injuries, Dame made his presence loud and clear in Milwaukee, and he knows the crowd appreciates the same.
“I think when people look back it, people will respect my time there. At the end of the day – before I got there, who was at point guard producing the way I produced? I mean, there was nobody. And they won it before I got there, but as far as me personally, I thought I showed up regardless of what my circumstances might have been personally or whatever the case may be. I showed up, I did what I had to do. I adjusted. I showed up. I never shied away from anything.” It may not have ended in a championship parade, but Damian Lillard gave what he could. And now, as he moves on, the memories — especially those shared with Giannis — seem to mean just as much.
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Could Lillard and Giannis have been the NBA's most dominant duo if given more time?