Bucks' Damian Lillard: Playing For Blazers Again 'How I've Felt My Career Will End'

Don't be shocked if Milwaukee Bucks superstar Damian Lillard eventually finds his way back to the Portland Trail Blazers at the end of his playing days.

"This is always how I've felt my career would end," he told reporters on Wednesday when asked if he could ever see himself playing for the Blazers again.

Barring some sort of surprising trade, Lillard won't be going anywhere soon. He's under contract through the 2025-26 season and has a $58.6 million player option in 2026-27 he'll almost assuredly exercise, so the earliest we'd likely see Dame back in Portland would be ahead of the 2027-28 campaign.

Well, outside of when he plays against the Blazers on the road, as he's doing on Wednesday night for the first time since being trade to Giannis Antetokounmpo's Bucks.

"I expect it to be a lot of love, honestly," Lillard told reporters regarding his return. "I've always had a great relationship with the city and a great relationship with the fans. I don't see that changing at all. We had a lot of great times, a lot of high moments, and we've shared some low moments. We was always in the fight. We always had sell out crowds, and I showed up and did what I needed to do, every night."

Returning was strange for Lillard, however, especially considering he'd only gone to the home locker room for the first 11 seasons of his career.

"I didn't know where to go," he told reporters. "I'd never been to the visitors' locker room until today."

The change in scenery has potentially given Lillard something he never really had in Portland—a legitimate chance to win a title. While his start in Milwaukee hasn't been all smooth sailing, as evidenced by the quick firing of former head coach Adrian Griffin in favor of Doc Rivers, Lillard's Bucks are still 32-15 and second in the Eastern Conference.

The one-two punch of Giannis and Dame is as good as any in the NBA, and Antetounkoumpo's MVP pedigree and his previous title—combined with Lillard's penchant for coming up huge in the clutch—makes them a scary duo come the postseason.

Eventually, Lillard may return to Portland to finish his career. But if he doesn't do so with a ring from his time in Milwaukee, it may feel like a bittersweet return.