Tatum’s Relationship with Lillard: A Key Factor in Celtics’ Free Agency Strategy

Boston Celtics Eyeing Damian Lillard

As the Boston Celtics contemplate their roster options this offseason, one name emerging as a potential target is Damian Lillard, who was recently released by the Milwaukee Bucks. The Celtics, alongside other prominent teams such as the Los Angeles Lakers and Golden State Warriors, are reportedly interested in acquiring the nine-time All-Star, raising questions about Lillard’s willingness to join Boston.

Potential Interest from Lillard

Sources indicate that Lillard could indeed be intrigued by the prospect of playing for the Celtics, particularly due to his established rapport with Jayson Tatum. According to insights from The Boston Globe, Lillard has a long-standing friendship with Tatum, which may play a pivotal role in his decision-making.

Both players experienced significant Achilles injuries during the 2025 NBA playoffs — Lillard on April 27 and Tatum on May 12 — and are expected to miss much of the following season. This shared experience may not only bond them further but also foster a desire to support each other during rehabilitation, potentially making Boston a favorable option for both athletes as they eye the 2026-27 season.

History of Friendship

Their relationship began to solidify back in 2021 when Lillard encouraged Tatum to represent Team USA in the Tokyo Olympics, a move that culminated in a shared gold medal victory. Additionally, their children have shared moments together, adding a family dimension to their friendship.

In the summer of 2023, after Lillard expressed a desire to leave the Portland Trail Blazers, Tatum reportedly pursued Lillard, promoting the idea of him joining the Celtics. Despite Tatum’s efforts, Lillard was eventually traded to the Bucks, which inadvertently led to the Celtics acquiring Jrue Holiday.

Future Considerations

Transitioning into the future, acquiring Lillard comes with inherent risks. At 36, his health is a concern, especially given his history of injuries, including a serious blood clot issue earlier in the year. However, Lillard might consider a contract closer to the veteran minimum, as he is still set to receive $22.5 million per year from Milwaukee over the next five seasons.

As the Celtics navigate this uncertain offseason, they must decide whether to pursue Lillard or focus on rejuvenating their roster around existing talents like Tatum, Jaylen Brown, Derrick White, and Payton Pritchard. Tatum reportedly hopes to convince Boston’s management to take a chance on Lillard, aligning with his vision from two summers ago. Lillard’s history and connection with Tatum could very well influence his potential move to Boston, adding a compelling narrative to the Celtics’ pursuit of their next franchise player.