The Boston Celtics are gearing up for a transformative offseason as they navigate the implications of Jayson Tatum's Achilles injury while seeking to maintain their championship stature. With Tatum sidelined for a significant portion of the 2025-26 season, the Celtics, under new ownership, are considering bold moves this summer. The recent release of Damian Lillard by the Milwaukee Bucks has piqued Boston's interest, potentially pairing him with Tatum upon his recovery.

Lillard, a nine-time All-Star, could be a strategic addition to a Celtics roster that has already seen the departure of pivotal players like Jrue Holiday and Kristaps Porzingis. Despite being on the older side at 34, Lillard’s impressive scoring average of 24.9 points per game before his injury makes him a potentially valuable asset as Boston seeks to reestablish its competitive edge. The Celtics aim for long-term flexibility while remaining a contender in the league.