The Boston Celtics are overwhelming favorites to sign 9-time All-Star Damian Lillard ahead of the 2025-26 season, according to Brett Siegel of ClutchPoints.
The report lines up with other recent reports that have hinted at the former Portland Trail Blazers and Milwaukee Bucks guard joining Boston as a free agent.
The Boston Herald’s Zack Cox reported on July 14 that Lillard is “more receptive” to joining the Celtics than he was in 2023, when he requested a trade from the Bucks, which ultimately led to his acquisition by Milwaukee.
“Lastly, though Lillard reportedly is more receptive to joining Boston than he was in 2023, when the Celtics were linked to him before trading for Holiday, it’s unclear where his priorities lie this offseason,” wrote Cox.
Jayson Tatum Recruiting Damian Lillard
“The Celtics can offer Lillard a minimum contract, or a $5.7 million taxpayer mid-level exception if they make additional moves to dip back below the second apron of the luxury tax, which they exceeded with their recent signings of Garza and Minott.”
The report added that joining the Celtics would give Lillard “a realistic shot” at winning his elusive NBA championship in 2027, when both he and Tatum would have recovered from their Achilles injuries.
Tatum, who is also recovering from an Achilles tear, has been actively recruiting Lillard to join him in Boston, per The Boston Globe’s Gary Washburn.
“Damian Lillard remains a free agent but is considering his options, and the Celtics are indeed one of them,” Washburn wrote.
“The nine-time All-Star is in no hurry to sign, but the Celtics are interested in a multi-year deal that would allow him to return fully healthy from his torn Achilles for the 2026-27 season in a Celtics uniform along with a healed Tatum for a title run.”
“According to NBA sources, Tatum has been active in recruiting Lillard to Boston, and the market for the point guard is limited because his injury will prevent him from likely playing most of next season. Lillard sustained his injury on April 27, 15 days prior to Tatum’s injury.”
The Failed Stint in Milwaukee
It’s fair to suggest that Lillard and the Bucks were not a good match from the outset. The iconic guard admittedly wanted to land on the Miami Heat, but his wishes were not granted by the Blazers, who sent him to Milwaukee.
According to ESPN’s Tim MacMahon, Lillard was unhappy during his entire stint in Milwaukee and was thrilled when the organization used the stretch-and-waive provision that made him a free agent.
“He never wanted to be in Milwaukee,” MacMahon said on “The Hoop Collective” podcast, via SI.com. “He was a pro, and he tried to make the best of it. But again, he didn’t want to be there. He had to actively try to make sure he wasn’t miserable.”
Lillard averaged 24.6 points, 7.0 assists and 4.5 rebounds in 131 regular-season games for the Bucks. He appeared in only seven playoff games across two seasons due to a multitude of injuries. His stint ended with him tearing his Achilles during the 2025 playoff series against the Indiana Pacers, which will sideline him for next season.
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