Celtics Predicted to Land 9-Time NBA All-Star After Anfernee Simons Trade

Bleacher Report's Greg Swartz predicts the Boston Celtics will sign Damian Lillard after the nine-time All-Star guard was waived by the Milwaukee Bucks. Swartz suggests the Celtics, not pressured to win immediately due to Jayson Tatum's Achilles injury, could view signing Lillard on a team-friendly deal as a smart investment for a potential 2026-27 title run, assuming their core players remain.

Swartz indicates Lillard joining Boston depends on the Celtics successfully trading guard Anfernee Simons to shed salary. ESPN's Brian Windhorst reports that Celtics president Brad Stevens and the team are "actively" trying to trade Simons this summer, though the outcome is uncertain. Successfully trading Simons would allow the Celtics to use their $5.7 million taxpayer mid-level exception on Lillard. Swartz notes the Celtics' previous success acquiring veteran point guard Jrue Holiday from the Bucks, who helped them win the 2023 championship.

Lillard responded to reported interest from the Celtics and other contenders while he recovers from injury, posting on social media: "If they call it a 'gamble' at this stage… tell ’em this [is] the jackpot. #ToBeContinued."

The Bucks waived Lillard to sign center Myles Turner in free agency. According to The Athletic, the Celtics are among several contending teams, including the Golden State Warriors and Los Angeles Lakers, interested in signing Lillard despite his expected absence next season due to his Achilles injury. The Athletic also reported that Lillard was "elated" about being waived, as it gave him freedom to choose his next team without financial constraints after the Bucks stretched the remaining $113 million on his contract.