Damian Lillard went to bed on Monday night trapped on a sinking ship. He was a member of a Milwaukee Bucks team desperately trying to reshape its roster to appease Antetokounmpo without him, as Lillard will presumably miss most or all of the 2025-26 season recovering from a torn Achilles tendon.

One NBA executive told ESPN’s Tim Bontemps and Jamal Collier that the Milwaukee Bucks waiving Damian Lillard turned a "bad situation into a worse one."

It was a stunning move when the Milwaukee Bucks traded for Damian Lillard. Two years later, he exits the team in dramatic fashion.