Damian Lillard Says He Has No Regrets About Long Road Back to Portland

Damian Lillard spent his first 11 NBA seasons with the Portland Trail Blazers, becoming a franchise icon and earning a place among the league's top 75 players. For all his long-range shooting and clutch moments, though, team success eluded him, and Portland reached the conference finals only once in that span.

In the summer of 2023, Lillard asked for a trade to a championship contender. What followed was a three-year stretch of drawn-out negotiations, a surprising move to the Milwaukee Bucks, a difficult pairing with star teammate Giannis Antetokounmpo and more playoff disappointment. In 2025, during a second consecutive first-round exit, Lillard tore an Achilles. Months later, Milwaukee waived him with two years and $113 million remaining on his contract.

Portland signed him in July 2025, and Lillard says the Blazers were the first team to call after the Bucks let him go. "I'm really thankful that as soon as I was waived, it was the first opportunity presented to me," he told NBC News on the eve of the season. "They knew that I wasn't gonna accept the injury and just be done. They knew how I was gonna respond to that."

His time in Milwaukee was not smooth. The Bucks changed head coaches during his first season there, and his chemistry with Antetokounmpo, who has since been traded, was repeatedly questioned. Even with Lillard averaging more than 24 points per game, the team lacked consistent success. Injuries hurt both playoff runs, and the two stars shared the court in only four postseason games, winning one. Lillard also described the period as "lonely" because his family stayed in Portland.

Still, he believes the detour was worthwhile. "I don't regret any part of the journey. I feel like it was all necessary," Lillard said. "The team that I'm on now couldn't be formed if I had never left." He said the rebuild gave Portland the chance to develop young players and gather assets.

That claim holds up in the roster's makeup. The trade with Milwaukee brought Toumani Camara and Deni Avdija to Portland, and the rebuild produced the draft pick used on Donovan Clingan. Milwaukee's decision to waive Lillard also let him sign a team-friendly deal with the Blazers. He missed all of last season recovering from the Achilles tear, while Portland made the playoffs without him. This summer the team added former All-Star Ja Morant, raising fresh questions about how Lillard would fit alongside another high-profile guard.

So far the answers look encouraging. The Blazers are 2-0 heading into Tuesday's game against the Los Angeles Lakers, set for 10 p.m. ET on NBC and Peacock. Lillard scored 25 points in the opener and 19 in a win over Sacramento, averaging just 28.5 minutes. First-year head coach Micah Nori has spread playing time across a versatile group that also includes Jrue Holiday and Scoot Henderson. Avdija leads the team at 30.5 minutes per game.

Lillard said the team's balance has changed his burden. "I don't feel overwhelmed with responsibility," he said, adding that the roster is built so he can have a great season without exhausting himself and arrive at the postseason healthy. Morant echoed the sentiment, saying that if everyone is unselfish and ego-free, "there shouldn't be no problems."

It is still very early, and Portland has not yet faced the adversity Lillard says is certain to come. But he sees the same opportunity that prompted his trade request three years ago: a chance to win. "I expect our team to have a great season," he said.