“Sometimes what didn’t work out for you really worked out for you.” Damian Lillard summed up his tumultuous time with the Milwaukee Bucks in a not-so-cryptic way. Now he returns to Portland, the same team he left to win a championship alongside Giannis Antetokounmpo. The duo dominated the stat sheets, yet the championship column during their time remained empty. Some have already written a thesis on why they didn’t work together. But let’s hear from the 35-year-old guard, who can tell us exactly what went wrong.

At the beginning of the month, out of nowhere, the Bucks announced waiving Dame, who is still recovering from his Achilles injury. In fact, they were even quick to sign Pacers center Myles Turner as a replacement. Two back-to-back shocking news stories, some reports even suggested Giannis was all-in on the plan. However, when it comes it Lillard, he doesn’t feel his time in Milwaukee was incomplete. “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…and I think we just had bad luck.”

Bad luck is the right way to sum up his time with the Bucks. His move was full of fanfare and expectations of another championship. Instead? Two years, two brutal first-round exits, a scary health scare, and an Achilles tear is what fate had in store for Dame Time. Which is exactly what the 9x All-Star explained to the Milwaukee Journal Sentinel. “My first year (2023-24) people complained a lot, the Bucks this, the Bucks that, but we was the two seed pretty much the whole season until the very last game and end up being the three seed.”

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They had a 49-33 record as the team underwent multiple head coach changes. First, they dismissed head coach Adrian Griffin, despite having a 30–13 record. Joe Prunty was the interim until Doc Rivers’ signature was secured. Yet, the hopes of playoffs were dashed when Giannis was out for the first round and the team bowed out to the Pacers. This year’s the effect of the injuries was no different, Lillard recalled, “Then this year, I missed Game 1, played Game 2 and Game 3 and get hurt at the start of Game 4. So, I mean, the healthy part we just didn’t have.” But that was not the only apparent problem.

“I think a lot of people for me personally was like, ‘We want to see Dame do this and Dame do that’, but I’m playing with a 30-plus point per game scorer, a guy who plays with the ball in his hands the same way I’ve done my whole career.” Two ball-playing stars gelling together was always the question the Bucks duo faced. For context, a season before Damian Lillard’s arrival, Giannis had a usage rate of 38.5%, the highest of his career. The same year, for the Blazers, Dame too had a career-high usage rate of 33.7%.

For their first year together (23-24), the percentages dropped as the Greek Freak would average 32.8% and Lillard with 28.3%. That’s why Damian called his time unfair. “So I think it’s kind of unfair how people was like Dame (isn’t the same) because of the way I played in Portland. I had the ball all the time, so it just looked different. But I think for how productive I actually was I think it’s been viewed unfairly.” With Portland, Lillard already found a place to thrive, and it seems a location change is in Giannis’ future, too.

After Damian Lillard, can the Bucks survive without Giannis Antetokounmpo?

After winning the NBA title in 2021, Antetokounmpo and the Bucks have tried to make it back to the mountaintop, but they haven’t been able to find that same success. The Bucks waived and stretched the remaining nine figures left on Damian Lillard‘s contract to make enough room to sign Turner from the Pacers. By releasing Dame, there was a void for a point guard. The Bucks filled it with Anthony Cole, who is looking to find his best form apart losing his place on the Magic roster. But will it be enough to keep the Greek Freak tied to a longer contract?

Antetokounmpo has a $62.7 million player option with the Bucks for the 2027-28 season. This simply means the 2x MVP could hit the open market as early as the summer of 2027. NBA analysts and insiders Bill Simmons and Zach Lowe believe the LA Clippers are gearing up to make a push for Giannis. “I think that’s their endgame, that Summer in 2027. ‘Short term? Let’s try to win. Long term? Giannis,’ and that’s how they’re thinking.”

This year, before Damian Lillard’s departure, there were already reports of the team circling Giannis Antetokounmpo. Lakers, Warriors, and Celtics were a few of the possible destinations. But those talks turned cold soon, but with the Clippers update, it seems the Bucks and Giannis’ future might come to an end. The team will have to figure out something to keep him for a longer time.