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.

Portland Trail Blazers guard Damian Lillard shared Jrue Holiday’s message after Bucks release, teasing backcourt that ended up materializing.

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.