Do the Celtics really have interest in signing Damian Lillard — and would Lillard really have interest in coming to Boston?
The answer to both of those questions might be yes.
The Celtics — along with the Los Angeles Lakers and Golden State Warriors — are “known to be among the many teams” eyeing Lillard on the free-agent market after the Milwaukee Bucks reportedly waived the nine-time All-Star on Tuesday, per The Athletic.
And according to The Boston Globe’s Adam Himmelsbach, the Celtics could be on Lillard’s radar as well.
“A league source also made it clear that Lillard could have interest in Boston, too, citing his respect for the organization and his long friendship with (Jayson) Tatum,” Himmelsbach wrote Wednesday.
Lillard’s “long friendship” with Tatum is worth exploring, especially since both players suffered serious Achilles injuries during the 2025 NBA playoffs — Lillard on April 27; Tatum on May 12 — and are expected to miss most or all of the 2025-26 season. If Lillard wants a rehab partner and has a desire to play alongside Tatum in 2026-27, that could make Boston a more intriguing destination for him.
So, how far do Lillard and Tatum go back? The two All-Stars appeared to have a close relationship as early as 2021, when Lillard contacted Tatum and convinced him to play for Team USA at the Summer Olympics in Tokyo, per ESPN’s Brian Windhorst.
Lillard and Tatum won a gold medal together that summer in Tokyo, with their young children even spending some time together as USA Basketball prepared for the Olympics in Las Vegas. (Tatum’s son Duece was born in 2017, while Lillard’s first son Damian Jr. was born in 2018.)
In the summer of 2023, after Lillard requested a trade from the Portland Trail Blazers, Tatum pitched the veteran guard on joining him in Boston, with Andscape’s Marc Spears reporting that Tatum “tried to get in (Lillard’s) ear” about coming to the Celtics.
Tatum’s recruiting efforts fell short, as the Blazers traded Lillard to the Bucks in a deal that helped bring Jrue Holiday to Boston. But the fact that Tatum wanted Lillard in Boston just two years ago is certainly relevant now as the Celtics explore their options in an uncertain offseason.
Signing Lillard would have its obvious risks; he’ll be 36 years old at the start of the 2026-27 season and has missed at least 24 games in three of the last four seasons. While Lillard’s talent is undeniable, there’s no guarantee he’d return to All-Star form after an Achilles surgery at age 34 — which came on the heels of a scary blood clot issue back in March.
Lillard may not cost much, however, and could accept a deal close to the veteran minimum while he’s paid the remainder of his contract with Milwaukee ($22.5 million annually over the next five years).
Whether the Celtics want to go down that path with Lillard or continue their full roster “reset” by getting younger around their core of Tatum, Jaylen Brown, Derrick White and Payton Pritchard remains to be seen. But at the very least, we’d imagine Tatum will advocate for Boston taking a chance on Lillard to realize his vision from two summers ago.
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