Damian Lillard’s return to the Portland Trail Blazers could have significant ramifications for Giannis Antetokounmpo’s future with the Milwaukee Bucks.
Lillard signed a three-year deal with his former team to make for a fairy tale homecoming. The nine-time All-Star is a legend in Portland, having led them to the Western Conference Finals in 2019 and making a series of iconic playoff game winners.
On the other side of this equation is the team Lillard left, the Milwaukee Bucks, who are desperately attempting to cling to their MVP and NBA champion Antetokounmpo. So what does this news mean for him?
Giannis Antetokounmpo should learn from Damian Lillard’s story, says NBA analyst
Lillard initially left the Trail Blazers in search of an NBA title. He was traded to Milwaukee, not one of his desired landing spots, to be paired with one of the NBA’s all-time greats Antetokounmpo, making them one of the title favourites.
Ultimately, the Bucks didn’t sniff a title. They lost to the 2025 NBA Finalists Indiana Pacers in the first round in both seasons with Lillard. Milwaukee then waived Lillard after his Achilles tear, allowing him to look for another team on the open market.
Lillard’s time with the Bucks wasn’t a happy one. He struggled on a personal level to adjust to life in Milwaukee. The grass wasn’t greener there.
Kevin Wildes, on First Things First, said that Antetokounmpo can take lessons from this journey.
He said, “Giannis just saw a guy come to his team, and he said he was going through some personal stuff, and he would go back to his condo and watch boxing on YouTube. He was not happy.
“I bet if he had the opportunity and he could get into a time machine, he would go back to Portland and not do that trade. As soon as he’s available to do it, he goes back.”
Wildes continued, “If I’m Giannis, I’m like you know what, bouncing around from towns isn’t necessarily going to work. I just saw it not work with a guy on my team, and it didn’t work.”
If Antetokounmpo leaves, he could join a long list of players who left a team where they were beloved to chase a ring, and were unsuccessful. But if he stays, who knows when the Bucks can be competitive?
Milwaukee Bucks hamstrung by Damian Lillard contract
A problem for Antetokounmpo is that in their desperate attempts to keep him on the team, the Bucks continue to cripple their future chances.
Milwaukee waiving Lillard means they owe him $112,583,016 over the next five seasons, meaning they have over $22 million less cap space available to them for the next half decade.
Antetokounmpo, understandably, wants to win now, and rumours of his unhappiness have forced the Bucks to make questionable moves as they try to build a winning roster around him. They waived Lillard to sign Myles Turner, but in doing so, sold out their future.
So while he may decide to stay for the short term, it’s only going to get harder to imagine him winning another title in Milwaukee.