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.

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.

The Portland Trail Blazers got franchise icon Damian Lillard to sign a new contract with the team as he returns to his roots. Lillard's family is based in Port

The Milwaukee Bucks waived Damian Lillard this offseason after he spent two years with the team from 2023 to 2025. When the Bucks first acquired Lillard, there were high expectations that he and Giannis Antetokounmpo would potentially bring the Bucks another title together.

Marc Stein revealed the Celtics' level of interest in Ben Simmons after losing the Damian Lillard sweepstakes.

In celebration of the ink drying on his new contract, Damian Lillard and the Portland Trail Blazers hosted an introductory press conference on Monday evening, where the veteran point guard got real about his mindset after suffering a season-ending Achilles tear during the 2025 playoffs.

Injuries stood in the way both years as Antetokounmpo and Lillard battled ailments in the playoffs. The latter tore his Achilles tendon this past postseason, which brought an end to his time in Milwaukee and led to a reunion with the Portland Trail Blazers.