Damian Lillard and the Portland Trail Blazers have agreed to a three-year, $42 million contract. The deal is expected to include a player option for the 2027-28 season and also a no-trade clause. Lillard is rehabilitating his torn Achilles suffered in the first round of the playoffs and is not expected to play during the 2025-26 season.
Lillard was traded by the the Blazers to the Milwaukee Bucks ahead of the 2023-24 season following his trade request. The Blazers acquired Jrue Holiday as part of the original Lillard trade and then flipped him to the Boston Celtics. Portland acquired Holiday earlier this offseason, giving the team the possibility of pairing both veteran guards together.
The Bucks used the waive-and-stretch provision on Lillard as the $113 million remaining on his contract will be spread out over the next five seasons. Milwaukee utilized the maneuver in order to sign Myles Turner.
According to Marc Spears, Lillard was considering not exercising his $58.5 million player option for the 2026-27 season as living in Milwaukee away from his family had been a challenge.
Lillard had multiple meetings among general manager Joe Cronin and head coach Chauncey Billups as they discussed reuniting. Lillard had interest in remaining with the Blazers for his entire career, but requested a trade as free agency began in 2023 as it was clear the team was embarking on a rebuild around Scoot Henderson and Shaedon Sharpe.
