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.

A video went viral in 2023 when Jrue Holiday and Damian Lillard were caught having a conversation prior to a Celtics-Bucks matchup. It turns out, Lillard was having issues in the house he rented from Holiday.