When Damian Lillard walked away from Portland in 2023, the plan was crystal clear: team up with Giannis Antetokounmpo and chase the championship that had eluded him for over a decade. Two years later, that dream lies shattered alongside his torn Achilles tendon. Now, in one of the most emotional returns in recent NBA history, Lillard has come full circle, signing back with the Trail Blazers, where his legendary career began.
Why Did Damian Lillard’s Milwaukee Experiment Fall Short?
After being selected by the Blazers out of Weber State with the sixth overall pick in the 2012 NBA Draft, Lillard spent 11 years in Portland. He became the fourth player to be unanimously named Rookie of the Year and reached the Western Conference Finals in 2019 before being dealt to the Milwaukee Bucks before the 2023 season. Pairing Lillard with two-time MVP Antetokounmpo seemed like a solid strategy to cement the Bucks as one of the NBA’s elite teams.
However, things didn’t work out in Milwaukee. In each of Lillard’s two seasons with the Bucks, they were sent home in the first round by the Indiana Pacers. To make matters worse, in the 2025 postseason, Lillard suffered a torn Achilles, which may cost him the 2025-26 season.
The Bucks ultimately waived Lillard via the stretch provision so they could make room to sign center Myles Turner away from the Pacers, making Lillard a free agent.
Despite numerous rumors about where Lillard could wind up, he admitted that he never felt right leaving the Blazers and “not being at home” and ultimately decided to head back to Portland on a three-year, $42 million deal.
“It never felt right not being home,” Lillard said. “Through it all, I found my way back. It all just feels right.”
How Did Jrue Holiday Help Recruit Lillard Back to Portland?
Blazers fans are thrilled to have their fan favorite back home, but they also have another former point guard in the fold. Jrue Holiday left the Bucks for the Blazers when he was dealt to Portland in the trade that brought Lillard to Milwaukee. Holiday never played a game in Portland and was dealt to the Boston Celtics, where he helped them win a championship in 2024.
Following the Celtics’ second-round playoff exit at the hands of the New York Knicks in the 2025 postseason, which featured Jayson Tatum’s injury (also a torn Achilles), the Celtics decided to deal some of their higher-salaried players. They sent big man Kristaps Porzingis to the Atlanta Hawks and traded Holiday back to Portland for guard Anfernee Simons and two second-round picks.
Once Holiday arrived in Portland, he started talking about the Blazers with Lillard, which included a little recruiting pitch.
“You know, once he came here, I was like man, he was like Can I wear your number but he was joking and I was like nah you can’t wear my number,” Lillard said. “And it was just like a joke but then as soon as I was waived and obviously he knows that I live here and built my home here and stuff so he just like sent me the eyeball emoji.”
“As soon as I got waived, he sent me the👀emoji”
Dame says Jrue texted him recruiting him to Portland and asked to wear #0 ðŸ˜ðŸ¤£
(Via @trailblazers) pic.twitter.com/WFjm3xOZUB
— Bleacher Report (@BleacherReport) July 24, 2025
Although the eyeball emoji seems like a foolproof pitch, Lillard already knew where he wanted to be.
“I kind of knew already – I already knew where I was pivoting too when he sent it but I just didn’t want to say anything too soon and here we are.”
Although they may not be a championship contender and Lillard may not see the court during the 2025-26 season, he’s back where he belongs. It will be exciting to watch Lillard again take the court in a Blazers uniform.
