In a stunning twist that sent shockwaves through the NBA, the Boston Celtics were tantalizingly close to landing superstar Damian Lillard during the recent free agency period, only for the Portland Trail Blazers to swoop in and bring their hometown hero back to Oregon. The dramatic saga, filled with high-stakes recruiting and personal considerations, has left Celtics fans wondering what could have been.
After being waived by the Milwaukee Bucks, Lillard found himself at the center of a fierce bidding war. According to ESPN’s Shams Charania, over a dozen teams dangled minimum and mid-level exception offers in front of the All-Star guard. Among them, the Boston Celtics and Minnesota Timberwolves emerged as the frontrunners, with Lillard engaging in direct discussions with both franchises. Reports even indicate that Celtics star Jayson Tatum personally spearheaded the recruiting effort, making a compelling case for Lillard to join Boston’s championship chase.
However, the Celtics faced significant hurdles in their pursuit. Lillard, a West Coast native with deep family ties in the region, reportedly struggled to adjust to life in Milwaukee during his stint with the Bucks. The prospect of moving to Boston, another East Coast city, may have given him pause. Additionally, Boston’s financial constraints limited their offer to a taxpayer mid-level exception—a modest deal compared to the more lucrative contract Portland could provide. Despite these challenges, the Celtics remained firmly in the race, showcasing their ambition to pair Lillard’s lethal scoring with their already formidable roster.
The plot thickened with the revelation of Lillard’s devastating Achilles injury, sustained during the NBA playoffs. The injury will sideline him for the entire 2025-26 season, rendering the first year of any new contract effectively void as he focuses on rehabilitation. With a potential return slated for the 2026-27 season, questions linger about whether Lillard, an undersized guard known for his explosive ball-handling and long-range shooting, can reclaim his All-Star form. Achilles injuries often sap athleticism, and at this stage in his career, the road to recovery could be steep.
Shams: “Over a dozen teams made minimum and midlevel exception offers to Dame. Two teams in particular I’m told that Damian Lillard really considered: Celtics and the Timberwolves. He held calls with both teams at different points” pic.twitter.com/I8HmWzF8wm
— Oh No He Didn’t (@ohnohedidnt24) July 18, 2025
For Boston, signing Lillard represented a low-risk, high-reward gamble. His addition wouldn’t have altered their immediate plans for the upcoming season, given his injury, but it could have reshaped their long-term outlook. However, the Celtics’ front office is also grappling with payroll concerns, aiming to trim costs while maintaining their championship core. Adding another star, even one of Lillard’s caliber, could have strained their financial flexibility further.
In the end, Lillard chose to return to Portland, where his legacy as a Trail Blazers icon and his deep connection to the community proved too strong to resist. The decision leaves Boston to ponder a missed opportunity, while fans dream of what might have been—a dynamic duo of Tatum and Lillard lighting up TD Garden. For now, the Celtics will press forward, but the revelation of their near-miss with Dame Time will linger as one of the offseason’s most tantalizing “what-ifs.”