Jayson Tatum is working to bring another star to the Boston Celtics, as Gary Washburn of The Boston Globe reported that Tatum is trying to lure Damian Lillard to town (subscription required). Unfortunately, like Tatum, Lillard suffered a torn Achilles in the 2025 playoffs. A couple of months later, the Bucks waived and stretched the rest of Lillard's contract to make room for Myles Turner.
Lillard will miss most of the 2025-26 season, if not all of it, rehabbing. The guard is considering his options since being released by Milwaukee, but because of his injury, there isn't a rush for him to sign with a new team. A deal could come through sometime this offseason, allowing Dame to rehab alongside Tatum with help from his new organization.
Washburn wrote that the consensus among executives at summer league is that the Celtics "have a chance in the Lillard sweepstakes." The goal would be for Dame to help Boston make another run for a title in 2026-27.
Lillard will turn 35 tomorrow (July 15), so by the time he suits up for his next team, he'll likely be 36, assuming he doesn't play next season. He isn't the player he was in Portland, and it's unknown how he'll look coming off an Achilles injury, but signing Dame to a "cheap" deal would be a good decision by Boston for more than one reason. Lillard could help the Celtics hoist the Larry O'Brien trophy again, making the Bucks look even worse for letting him go.
Damian Lillard helping Celtics win a title would haunt the Bucks for years
Milwaukee waiving and stretching Lillard's contract was a move of desperation, trying to get Giannis Antetokounmpo to hang around. It could come back to haunt the Bucks, as could losing Lillard for nothing while keeping his salary on the books.
The last thing Milwaukee fans want to see is another one of its top former players go to Boston and win a championship. It'd feel like déjà vu after the Bucks traded Jrue Holiday to the Trail Blazers in 2023 as part of the Lillard deal, which led to Boston acquiring him. Milwaukee helped a conference rival win a title.
Lillard could do the same in less than two years. In the world of today's CBA, low-cost, low-risk moves are more impactful than ever. The cherry on top of it all for Tatum and the Celtics would be screwing the Bucks in the process.