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.

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

Lillard now joins a reshaped Portland roster coming off a 21-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.