Los Angeles, CA, USA; Portland Trail Blazers guard Damian Lillard (0) holds the trophy after winning the three point contest during the 2026 NBA All Star Saturday Night at Intuit Dome. Kirby Lee-Imagn Images

Damian Lillard Explains Reason For Re-Signing With Blazers

Originally posted on Portland Trail Blazers on SI
By Logan Struck | Last updated Feb 18, 2026 6:58 PM ET

In the 2023 offseason, the Portland Trail Blazers made a shocking move to ship Damian Lillard to the Milwaukee Bucks in a three-team trade. Before this move, Lillard spent the first 11 years of his NBA career in Portland, but the opportunity to team up with two-time MVP Giannis Antetokounmpo in Milwaukee had to be too hard to pass up on.

However, after just two years with the Bucks and a torn Achilles in the 2025 playoffs, Milwaukee and Lillard parted ways. The nine-time All-Star hit the open market after being waived, and who did he decide to sign with? None other than the Trail Blazers.

Despite being out for the entire 2025-26 season, Lillard went to All-Star weekend to represent Portland in the Three-Point Contest. While at All-Star weekend, Lillard spoke about why he decided to sign with the Trail Blazers in the offseason.

"When I had an opportunity to go to any team, I picked this team. I picked the team because, for one, it's the team that I wanted to win a championship with all along. And two, the team is in position, in my eyes, to do that. Especially with me being a part of it. I think we do have a chance. It was an easy decision," Lillard said about re-signing with Portland.

“When I had an opportunity to go to any team, I picked this team.”

YOU’VE SEEN HISTORY. WITNESS THE FUTURE. pic.twitter.com/pnfXzVV4S0
— Portland Trail Blazers (@trailblazers) February 16, 2026

Lillard's legacy in Portland

Lillard has not seen much playoff success while in Portland, making it out of the first round just three times with one Western Conference Finals appearance, which resulted in a 4-0 sweep. Still, though, he is a Trail Blazers legend.

Lillard could have left Portland much sooner than he did, but he decided to stick with the franchise that drafted him sixth overall in 2012 for over a decade. And, after just two years away, he is already back.

It would be a fairytale ending if Lillard can help take this Trail Blazers team to the next level and compete for a championship for the next two seasons.

In his last healthy season as a Trail Blazer, Lillard averaged a career-high 32.2 points with 7.3 assists per game, and if Portland can even get a fraction of that version out of him next season as he comes off an Achilles tear, they could undoubtedly be a contender in the West.

At 35 years old, it is uncertain how Lillard will perform when he finally returns to the court, but if his Three-Point Contest win was any indication, there should be no worry.