CELTICS FAVORITES TO SIGN DAMIAN LILLARD

The Boston Celtics have emerged as the frontrunners to sign nineස‍‍nine-time NBA All-Star Damian Lillard, following his surprising waiver by the Milwaukee Bucks in July 2025. The move has sparked intense speculation about Lillard’s next destination, with Boston’s interest driven by a combination of strategic roster planning and a personal connection with Celtics star Jayson Tatum.

A Strategic Opportunity for Boston

Lillard, a proven scorer and playmaker, was waived by the Bucks to free up cap space for signing Myles Turner, with the remaining $112.6 million of his contract stretched over five years. This unique situation allows Lillard to sign with a new team for a relatively low cost, as he will continue to receive $22.5 million annually from Milwaukee. For the Celtics, who are navigating a challenging offseason after parting ways with key players like Jrue Holiday, Kristaps Porzingis, and Luke Kornet, Lillard represents a high-upside addition at a potentially team-friendly rate.

Boston’s interest in Lillard is not new. The Celtics were linked to him during his 2023 trade availability with the Portland Trail Blazers, when Jayson Tatum actively encouraged Lillard to consider Boston. However, Lillard initially had reservations about joining the Celtics, ultimately landing with the Bucks. Recent reports indicate a shift in his stance, with Lillard now open to Boston, largely due to his close friendship with Tatum, forged during their time together on Team USA at the 2020 Tokyo Olympics.

Tatum’s Role in Recruitment

Jayson Tatum’s involvement has been a significant factor in Boston’s pursuit. Reports indicate that Tatum, currently sidelined with an Achilles injury, has been “active” in recruiting Lillard, leveraging their personal connection. Both players suffered Achilles tears in April 2025, and a potential signing could see them rehabbing together, setting the stage for a formidable partnership in the 2026-27 season. This shared recovery timeline aligns with Boston’s long-term vision, as the team is reportedly prioritizing a championship push in 2026-27 over immediate contention in 2025-26, given Tatum’s likely absence for most of the upcoming season.

Financial and Roster Considerations

The Celtics’ ability to pursue Lillard hinges on their financial flexibility. Boston is currently just over the second apron of the luxury tax by less than $1 million after recent roster moves. Trading Anfernee Simons, acquired from Portland in exchange for Jrue Holiday, could free up additional cap space. If successful, the Celtics could offer Lillard the veteran minimum (approximately $3.6 million) for 2025-26, followed by the nontaxpayer mid-level exception (around $5.9 million) in 2026-27. This structure would allow Boston to build a potent lineup featuring Lillard, Tatum, Jaylen Brown, and Derrick White, positioning them as serious title contenders in 2026-27.

Lillard’s market is reportedly limited due to his age (he turns 35 in July 2025) and the severity of his injury. However, his proven track record—averaging 24.9 points and 7.1 assists per game with a 37.6% three-point rate in 58 games for the Bucks in 2024-25—makes him an attractive option for teams willing to wait for his recovery. The Celtics’ financial flexibility gives them an edge over other reported suitors, such as the Golden State Warriors and Los Angeles Lakers, who may face tighter cap constraints.

Risks and Rewards

Signing Lillard carries risks. At 36 years old by the 2026-27 season, and coming off a major injury, there’s no guarantee he’ll return to his All-Star form. His history of missing at least 24 games in three of the last four seasons adds to the uncertainty. Additionally, Lillard’s ball-dominant style may require adjustments to integrate with Tatum and Brown, and his defensive limitations could pose challenges alongside Boston’s current guard-heavy roster, including Simons and Payton Pritchard.

Despite these concerns, the potential reward is significant. Lillard’s playoff pedigree and offensive prowess could complement Boston’s core, creating a dynamic “Core Four” for a championship run. NBA insider Chris Mannix noted that Lillard’s reduced financial burden makes him a low-risk, high-reward option, especially for a team planning for the future.

Lillard’s Perspective

Lillard, currently rehabbing in Portland, is reportedly in no rush to decide, focusing on recovery and family. NBA insider Chris Haynes indicated that Lillard would only sign this offseason under the “right terms and conditions.” His recent social media post—“If they call it a ‘gamble’ at this stage… tell ’em this [is] the jackpot. #ToBeContinued”—suggests confidence in his ability to return to form, which could bode well for Boston’s ambitions.

Why Boston Leads the Pack

The Celtics’ combination of Tatum’s recruitment, financial maneuvering, and a long-term championship vision positions them as favorites to land Lillard. While other teams, including the Warriors and Lakers, have shown interest, Boston’s ability to offer a competitive contract and a clear path to contention in 2026-27 gives them an edge. As Bleacher Report’s Greg Swartz noted, Boston’s success with another Bucks cast-off, Jrue Holiday, who helped secure their 18th championship in 2024, sets a promising precedent.

As the offseason unfolds, all eyes will be on whether Boston can finalize a deal to bring Lillard’s “Dame Time” heroics to TD Garden, potentially reshaping the franchise’s future.