NBA Insider Reveals Potential Factor in Bucks Parting Ways With Damian Lillard

Guard Damian Lillard—now a free agent—is at a crossroads in a career that will doubtlessly end in Hall of Fame induction.

It's true that 2025 saw Lillard make his ninth All-Star appearance, and second with the Milwaukee Bucks. However, Lillard battled deep vein thrombosis during the season, tore his Achilles in the playoffs, and was reportedly waived Tuesday in the most shocking move of the NBA offseason thus far so his old team could sign center Myles Turner.

On Tuesday, longtime NBA insider Chris Haynes—often regarded as being a particular authority on Lillard—discussed a factor that may have gone into the guard's exit.

"Aaron Goodwin, Damian Lillard's agent, about a month ago reached out to the Bucks and informed them that Dame would like to rehab back home in Portland and stay with his kids," Haynes said in an NBA TV hit. "I was told that some people within the Bucks did not approve of that, and there was kind of some back-and-forth right there."

Lillard played 11 years for the Portland Trail Blazers and remains well-liked there, despite a messy departure after the 2023 season.

"I think that (exchange) might've gotten the ball rolling, or at least put some ideas in the heads of the Milwaukee Bucks that led to this decision," Haynes said.

More NBA on Sports Illustrated