Lillard now joins a reshaped Portland roster coming off a 36-win season. With the 35-year-old likely to miss most of the 2025-26 season recovering from injury, Holiday is expected to anchor the team alongside young talent like Scoot Henderson and Shaedon Sharpe.

The pair were seen talking on-court when Boston played the Bucks last season, but the chat had little to do with a Blazers team-up.

Damian Lillard and Jrue Holiday are set to be teammates for the first time as both have joined the Portland Trail Blazers this offseason. But they know each other well already. Lillard shared with reporters Wednesday that he rented Holiday's house the last two years in Milwaukee. And they bonded, you could say, over WiFi.