The Boston Celtics may be crafting a future championship duo in silence. With Jayson Tatum and Damian Lillard both recovering from Achilles injuries, the stars are aligning—literally. Tatum is actively recruiting Lillard, who just hit free agency after a stunning Bucks release. The twist? Boston could land the nine-time All-Star for a bargain, with Milwaukee still footing the bill. The comeback story practically writes itself.
Jayson Tatum’s personal pitch to Damian Lillard signals long-term plans for Boston Celtics’ futureDamian Lillard, who has made nine All-Star appearances and ranks fourth all-time in 3-point shooting, is now an unrestricted free agent after the Milwaukee Bucks waived him and stretched his remaining $103–113 million over five years—allowing them to clear cap space to sign Myles Turner to a 4-year, $107 million deal. Despite suffering a torn Achilles in the 2025 playoffs, Lillard is still a highly sought-after veteran, having averaged 24.9 points and 7.1 assists over 58 games last season.
In the mix of elite teams such as the Los Angeles Lakers and Golden State Warriors, Boston stands out, largely due to Lillard’s close ties with Celtics forward Jayson Tatum, a six-time All-Star and the 2024 NBA champion. The Boston Globe reports that Tatum has been actively working to recruit Lillard, taking advantage of their chemistry from Team USA and their shared recovery timelines. League executives in Las Vegas say this places the Celtics solidly in the competition.
The front office in Boston has the option to offer Lillard either a veteran's minimum or the taxpayer mid-level exception, which is roughly $5.7 million, without violating the second tax apron. Meanwhile, Milwaukee is still paying Lillard during the stretch, which means Boston can get a Hall-of-Fame-caliber guard at a great price. For Lillard, it's a low-risk chance to recover in a successful culture, with his guaranteed cash already secured.
Timing is still flexible. Lillard might hold off on signing until later in the offseason—or he could even skip the entire 2025–26 season—taking his time with rehab without feeling rushed. On the other hand, Boston has a complete 15-man roster, but two of those spots are non- or partially guaranteed, which gives them some flexibility. With Jayson Tatum also working on his Achilles rehab, the idea of two superstars making their comeback together in 2026–27 has really excited Celtics fans.
Also Read: Los Angeles Lakers begin quiet shift to Luka Doncic while LeBron James is left reacting not leading
Boston's pursuit of Damian Lillard is a blend of strategy, emotion, and future planning. By utilizing his relationship with Jayson Tatum, making savvy roster decisions, and the appeal of a championship environment, the Celtics could have found the right moment to acquire a veteran star at a low cost. For Lillard, this is a fantastic opportunity—heal, rebuild, and possibly start a title chase in green by 2026–27. The real question is whether he will take the plunge.
Jayson Tatum’s personal pitch to Damian Lillard signals long-term plans for Boston Celtics’ futureDamian Lillard, who has made nine All-Star appearances and ranks fourth all-time in 3-point shooting, is now an unrestricted free agent after the Milwaukee Bucks waived him and stretched his remaining $103–113 million over five years—allowing them to clear cap space to sign Myles Turner to a 4-year, $107 million deal. Despite suffering a torn Achilles in the 2025 playoffs, Lillard is still a highly sought-after veteran, having averaged 24.9 points and 7.1 assists over 58 games last season.
In the mix of elite teams such as the Los Angeles Lakers and Golden State Warriors, Boston stands out, largely due to Lillard’s close ties with Celtics forward Jayson Tatum, a six-time All-Star and the 2024 NBA champion. The Boston Globe reports that Tatum has been actively working to recruit Lillard, taking advantage of their chemistry from Team USA and their shared recovery timelines. League executives in Las Vegas say this places the Celtics solidly in the competition.
The front office in Boston has the option to offer Lillard either a veteran's minimum or the taxpayer mid-level exception, which is roughly $5.7 million, without violating the second tax apron. Meanwhile, Milwaukee is still paying Lillard during the stretch, which means Boston can get a Hall-of-Fame-caliber guard at a great price. For Lillard, it's a low-risk chance to recover in a successful culture, with his guaranteed cash already secured.
Jayson Tatum has been recruiting Damian Lillard to join the Celtics, per @GwashburnGlobe pic.twitter.com/W3A0PPUxdh
— NBACentral (@TheDunkCentral) July 13, 2025
Timing is still flexible. Lillard might hold off on signing until later in the offseason—or he could even skip the entire 2025–26 season—taking his time with rehab without feeling rushed. On the other hand, Boston has a complete 15-man roster, but two of those spots are non- or partially guaranteed, which gives them some flexibility. With Jayson Tatum also working on his Achilles rehab, the idea of two superstars making their comeback together in 2026–27 has really excited Celtics fans.
Also Read: Los Angeles Lakers begin quiet shift to Luka Doncic while LeBron James is left reacting not leading
Boston's pursuit of Damian Lillard is a blend of strategy, emotion, and future planning. By utilizing his relationship with Jayson Tatum, making savvy roster decisions, and the appeal of a championship environment, the Celtics could have found the right moment to acquire a veteran star at a low cost. For Lillard, this is a fantastic opportunity—heal, rebuild, and possibly start a title chase in green by 2026–27. The real question is whether he will take the plunge.
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