The Boston Celtics recently missed out on securing Damian Lillard, who opted to sign with the Portland Trail Blazers for a lucrative three-year deal worth $42 million. Despite attempting to keep their offers competitive, the Celtics' financial limitations, as they work to avoid the luxury tax, hindered their pursuit. General Manager Brad Stevens made moves by trading Jrue Holiday and Kristaps Porzingis to ease their financial situation.

Lillard's fit with the Celtics was already questionable, given his need for the ball in his hands. The uncertainty surrounding his performance following an Achilles injury also raised concerns, especially with him nearing 36. Now that Lillard is off the table, Boston's management must continue evaluating ways to rebuild their roster, targeting a return to contention as Jayson Tatum recovers from his own Achilles injury expected by the 2026-27 season.