The Milwaukee Bucks are making significant changes in hopes of overcoming their playoff struggles. After three consecutive first-round exits, the team has added center Myles Turner in free agency, following Brook Lopez's departure to the Los Angeles Clippers. This move led to the difficult decision to waive Damian Lillard, who is now a free agent as he recovers from an Achilles injury. Lillard, a nine-time All-Star, is expected to attract interest from various contending teams.

One potential landing spot for Lillard is the Boston Celtics. While they are currently dealing with Jayson Tatum's Achilles injury, the Celtics could position themselves for a title run by signing Lillard to a team-friendly deal. If they manage to trade Anfernee Simons and clear additional salary, they could open up the resources needed for a multi-year contract with Lillard, making it a calculated risk worth taking.