Damian Lillard is set to become a free agent for the first time in his NBA career. Lillard will be waived-and-stretched by the Milwaukee Bucks after the NBA moratorium ends on Sunday afternoon. Upon clearing waivers, Lillard will be free to pick his next team.

One team Lillard has interest in joining is the Boston Celtics. And the Celtics reportedly have shared interest in teaming up with the veteran point guard.

When Lillard was seeking a trade from the Portland Trail Blazers two years ago, he wasn't interested in a trade to Boston. Now, Lillard has some interest in the Celtics, in part because of the close friendship he's built with star forward Jayson Tatum.

Boston is resetting their roster this offseason, as the team has deals lined up to get themselves under the second apron. The Celtics will be without Tatum for most, if not all, of next season as he recovers from a torn Achilles tendon. The same is true for Lillard, who also suffered a torn Achilles, earlier in the postseason. The idea behind signing the veteran star would be to line things up for the 2026-27 season, when both Tatum and Lillard should be fully recovered from their injuries.