Damian Lillard had never been off an NBA roster until the summer of 2025, after a torn Achilles and a surprise release left him stuck. The Portland Trail Blazers guard, 36, called that period his career’s darkest, according to Andscape’s Marc J. Spears, who interviewed him Oct. 20 about his exit from the Milwaukee Bucks.
He never suited up for Milwaukee again. Roughly three months on, the Bucks waived him and stretched his contract so they could add Myles Turner, part of a failed push to keep Giannis Antetokounmpo. The Miami Heat landed Antetokounmpo in June anyway.
By his own account, he learned of the move from an online post, not from the Bucks. He’d been in Milwaukee only two seasons, after 11 in Portland and a 2023 trade request. The shock was still fresh in July 2025, when he spoke with the Milwaukee Journal Sentinel’s Jim Owczarski.
Free agency lasted two and a half weeks. In that span, he told Spears, he weighed sitting out the year and auditioning for teams once healthy. Retirement crossed his mind briefly, too, though that idea was about being around for his kids, not his Achilles.
Portland’s three-year, $42 million deal brought back the guard it drafted in 2012. Lillard sat out all of last season. The nine-time All-Star is set to return when Portland hosts the Phoenix Suns in its Oct. 21 season opener, nearly 18 months after the injury.
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