newsweek
For the first time in his professional life, Damian Lillard found himself without an NBA team in the summer of 2025. A torn Achilles and an unexpected waiver from the Milwaukee Bucks left the veteran guard in uncharted territory, a situation he recently called the darkest chapter of his career.
In an interview with Andscape's Marc J. Spears on October 20, Lillard recounted the moment that hit hardest. "The darkest day was when I was hurt and got waived," he said. "It wasn't a matter of, 'Am I going to get an opportunity?' It was just like, it was a possibility and a thought of mine."
The injury occurred on April 27, 2025, when Lillard ruptured his left Achilles tendon during a first-round playoff game against the Indiana Pacers. He never played another game for Milwaukee. About three months later, the Bucks waived him and stretched his contract to create salary-cap flexibility, a move aimed at acquiring Myles Turner in an effort to keep Giannis Antetokounmpo. The gambit failed, as Antetokounmpo was traded to the Miami Heat in June.
Lillard learned of his release not from the team but from an online post, adding to the shock. He had spent only two seasons in Milwaukee after 11 years in Portland and a 2023 trade request. "I think that's the craziest part of it is I left here with four years on my deal and in my mind I was gonna be in Milwaukee the next four seasons at least," he told the Milwaukee Journal Sentinel's Jim Owczarski in July 2025.
During a free agency period that lasted two and a half weeks, Lillard weighed sitting out the entire year and auditioning for teams once healthy. "And that was probably the darkest time, because I didn't really know which way I wanted to go," he told Spears. Retirement also crossed his mind briefly, though that thought was driven by a desire to be present for his children rather than concerns about his Achilles.
Ultimately, Lillard signed a three-year, $42 million deal to return to the Portland Trail Blazers, the team that drafted him in 2012. He sat out all of last season and is now set to make his comeback when Portland hosts the Phoenix Suns in its season opener on October 21, nearly 18 months after the injury.
Key Analysis
Lillard's journey underscores the harsh business realities of the NBA, where even franchise icons can be blindsided by roster moves. His return to Portland not only marks a physical comeback but also a emotional homecoming for a player who has always been synonymous with the Trail Blazers. As he steps back on the court, all eyes will be on whether the nine-time All-Star can recapture his pre-injury form and lead Portland back to contention.
Originally reported by newsweek.