Damian Lillard, the nine-time NBA All-Star, has entered free agency following a significant contract restructuring by the Milwaukee Bucks, marking the first time in his career he will explore new team opportunities. With preseason approaching, multiple franchises, including the Boston Celtics, have expressed interest in the 6-foot-2 veteran, who is focused on recovery from an Achilles injury while aiming to win an NBA championship.

After the Bucks decided to stretch the remaining $113 million on Lillard’s contract over five years, freeing salary cap space immediately, the 33-year-old guard is now free to choose his next destination. Boston is an intriguing option, especially after star forward Jayson Tatum suffered a season-ending injury, prompting the Celtics to recalibrate their title aspirations toward the 2026-27 season. Though Lillard seems to fit their long-term plan, skepticism remains regarding this potential partnership.

Analysis of Lillard’s Free Agency Outlook and Boston Celtics Interest

Lillard’s current free-agent status is unique because the Bucks continue to pay his salary despite waiving him, which removes financial pressure from his choice and allows him to prioritize his rehabilitation and championship pursuit. The Celtics’ plan to build around a rejuvenated core by the following season aligns with Lillard’s recovery timeline and his desire for a title run. However, not all analysts are convinced this move will materialize.

NBA insider Jake Fischer, speaking on The Garden Report with Bobby Manning, expressed doubt about Lillard’s likelihood to join Boston. Fischer speculated that Lillard might prefer to delay signing and instead position himself as a high-value midseason acquisition, depending on his recovery and opportunities at that time. He emphasized the advantages of this approach, particularly for maximizing rehabilitation support.

“I think he has every reason not to sign, right, and just kind of wait it out and be like the big mid-season acquisition somewhere. If he wants to sign somewhere now. I mean, the most benefit he would have is to get full support for his rehab.” —Jake Fischer, NBA Insider

Fischer also noted Lillard’s financial security and lifestyle preferences could affect his decision. Having earned hundreds of millions during his career and owning a sizeable estate in Portland, Lillard’s motivation appears less driven by money and more by personal and family considerations.

“He’s made hundreds of millions of dollars in his career. He’s got this whole estate out in Portland where he spends most of his time in the offseason and stuff, as is like I don’t think he has any reason to do that.” —Jake Fischer, NBA Insider

Those close to Lillard understand he values family highly, which could complicate the logistics of relocating to Boston if that move proceeds. Currently, no official confirmation exists regarding Lillard’s plans, and speculation continues without concrete evidence of his next destination.

The Milwaukee Bucks’ Bold Contract Stretching Move and Its Implications

The Bucks’ decision to waive Lillard while stretching his contract payments over five years was one of the NBA offseason’s most audacious maneuvers. This action freed substantial cap space immediately but left Lillard’s $113 million salary on the Milwaukee books long-term. The move reflects the Bucks’ prioritization of cap flexibility to chase championships, even at the expense of parting with a nine-time All-Star still capable of making an impact.

This approach reframes the NBA offseason landscape, freeing Lillard to pursue new opportunities without a financial burden but leaving the Bucks to adjust their roster strategy accordingly. Lillard’s future now hinges on both his rehabilitation progress and his evaluation of teams’ ambitions and fit.

Potential Impact on the Golden State Warriors if Lillard Joins Boston

The Golden State Warriors were among the first to seize on Lillard’s availability, recognizing his elite scoring ability and pairing potential with Stephen Curry. Despite Lillard’s recent Achilles injury, his statistics remain impressive: averaging 24.9 points, 4.7 rebounds, and 7.1 assists per game, with shooting percentages of nearly 45% from the field, 37.6% from three-point range, and 92.1% from the free-throw line.

Lillard’s rare ability to consistently shoot from long distance complements Curry’s shooting prowess, potentially creating an offensively formidable backcourt duo. This offensive strength could revitalise the Warriors’ championship window, adding another threat that opposing defenses must respect.

However, if Lillard ultimately chooses the Celtics, the Warriors would lose a transformative player who might have extended their dynasty’s competitive lifespan. Lillard’s decision, therefore, carries substantial strategic consequences, not only for the Celtics but also for Golden State and the wider league.

The Uncertainty Surrounding Lillard’s Final Choice

While speculation swirls about Lillard teaming up with Jayson Tatum in Boston, no definitive sign points toward a finalized deal. The situation remains fluid, with Lillard’s health and personal preferences playing critical roles. His value as an elite scorer who can change playoff dynamics ensures that any team acquiring him gains a significant boost. Conversely, not signing Lillard now keeps options open for a midseason acquisition, which could shift the balance of power as the season unfolds.

As preseason approaches, the bubble of speculation surrounding Damian Lillard’s next move grows, with Boston and Golden State representing the most captivating possibilities. How this decision unfolds will likely influence title races, shape team strategies, and define the narratives of the 2025-26 NBA season.