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The Boston Celtics and Damian Lillard could be on a collision course. After being waived by the Milwaukee Bucks in a surprise salary-cap maneuver to make room for Myles Turner, Lillard is now an unrestricted free agent for the first time in his career. The Celtics, fresh off a massive roster reshuffling, are reportedly among the most interested suitors, and The Boston Globe's Gary Washburn says the interest is mutual.
While Lillard wasn’t keen on joining Boston a few years ago, things have changed. He now sees Boston as a serious contender and is close friends with Jayson Tatum, with whom he played on Team USA in the 2020 Tokyo Olympics. Their bond could play a pivotal role as both recover from Achilles injuries, with eyes on a return in the 2026-27 season.
Lillard, a nine-time All-Star and seven-time All-NBA selection, averaged 24.9 points, 4.7 rebounds, and 7.1 assists last season before suffering a torn Achilles in the playoffs. While the injury will keep him sidelined for the 2025-26 season, his résumé, including ranking fourth all-time in 3-pointers made, speaks for itself. A future Hall of Famer, Lillard brings leadership, scoring, and clutch ability, all qualities Boston has long sought at the point guard position.
Boston’s offseason has been about long-term positioning. With the trades of Jrue Holiday and Kristaps Porzingis, the Celtics opened cap flexibility while resetting their roster. They’re likely operating under the first salary cap apron, meaning they can offer Lillard the $5.6 million taxpayer midlevel exception, a bargain given the Bucks are still paying most of his remaining salary.
Will it be Dame Time for the Celtics soon?
This year is a transition season for Boston, especially with Tatum also expected to miss the entire campaign. That makes Lillard an ideal fit. He can rehab alongside Tatum, serve as a veteran presence and mentor to Payton Pritchard and the team’s rookies, and prepare for a true championship push in 2026-27. With Tatum, Jaylen Brown, Derrick White, and rising prospects like Hugo Gonzalez in the fold, Boston’s core remains strong.
Celtics president of basketball operations Brad Stevens knows time is ticking. Tatum and Brown are entering their late 20s, the heart of their primes. Adding Lillard, even an aging version, would show Boston’s commitment to maximizing that window. His style of play, built on savvy and skill rather than athleticism, should age gracefully and fit seamlessly into the Celtics’ system.
There’s also minimal risk. If the fit doesn’t work, Boston can move on easily. But if it does, Lillard could be the missing piece in a championship puzzle. Compared to other options like Miami or Golden State, Boston offers the best mix of talent, opportunity, and stability for Lillard to chase the one thing missing from his résumé: a ring.
The Celtics have been searching for this type of leader since the Kemba Walker experiment fizzled out. With a potential second championship on the horizon and a path cleared financially and structurally, the Celtics should go all in.
