Damian Lillard himself admitted that fellow former Milwaukee Bucks guard Jrue Holiday recruited him back to the Portland Trailblazers earlier than anybody. It started when Holiday, who won the 2021 title with the Wisconsin organization, sent him a curious eyes emoji after the news of his waiving broke out.
Holiday was already traded to Portland this time and Lillard was released through a stretched-waive provision. The precursor to this move is the fact that Dame won’t be able to play a game in the 2025-26 season.
Lillard-Portland reunion is the most shocking development this summer but to his inner circle, they are probably not that surprised as reports claimed the idea of his return has been plotted in his early months with the Bucks.
ESPN’s James Collier wrote on Wednesday:
When Lillard returned to Portland to play his first game in a visiting uniform later that month, he was greeted with multiple video packages and a standing ovation.
The report added:
“I see a day where I’ll be in a Trail Blazer uniform again before I’m done,” Lillard said then.
Damian Lillard’s commitment to the Bucks should not be questioned
Although there is a desire to return to the city that loved him and adopted him, one cannot Lillard’s time with the Bucks. He was an All-Star in both seasons and together with Giannis Antetokounmpo made up the highest scoring duo last season.
The only problem the team had while he was with them was the injury either to him or Antetokounmpo in each playoffs.
Lillard said that is what he regrets, too.
“As a tandem with him, I felt like we can go and win it all with the two of us,” he said in an interview Jim Owzcarski of Milwaukee Journal Sentinel.
“We can go on a run and just dominate. I’m not sure I’ll ever experience that again. But it was great playing with him.”
The Greek Freak was the one injured in 2024 postseason and missed all six games and it was Lillard’s turn in 2025. Both times were elimination in the hands of the Indiana Pacers.
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