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.

An NBA insider believes the Milwaukee Bucks' controversial deal to acquire All-Star Damian Lillard numbers among the worst in league history.