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.

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.

With Damian Lillard returning to the Portland Trail Blazers over the weekend on a three-year deal, he will team up for the first time with guard Jrue Holiday, who was traded from the Boston Celtics to the Trail Blazers earlier this month.