The Boston Celtics’ attempt to add a major free agency acquisition ended abruptly on Thursday when Damian Lillard decided to re-sign with the Portland Trail Blazers on a three-year, $42 million deal. The move surprised many, as Boston had shown significant interest in acquiring the veteran guard despite his recent Achilles injury.

Lillard, who spent the last two seasons with the Milwaukee Bucks, was waived this offseason following a torn Achilles suffered during the 2025 NBA Playoffs—the same injury that later afflicted Celtics star Jayson Tatum. Due to this injury, Lillard is expected to miss the entire 2025-26 season and likely will not return to the court until he is 36 years old.

Celtics’ Strategy: Stashing Lillard for Future Impact

Even with concerns about Lillard’s recovery timeline, the Celtics considered signing him and carrying him through his rehab year, anticipating a strong impact when he returned for the 2026-27 season. This plan could have created a formidable lineup featuring Lillard alongside Jayson Tatum, Jaylen Brown, and Derrick White. However, Lillard ultimately chose to return to the Trail Blazers, the team where he spent the first eleven years of his career.

ESPN’s Shams Charania revealed that the Celtics were among two teams that Lillard seriously evaluated during free agency.

“Over a dozen teams made minimum and midlevel exception offers to Damian Lillard,”

Charania said.

“Two teams in particular I’m told that Damian Lillard really considered, and that’s the Boston Celtics and the Minnesota Timberwolves. He held calls with both teams at different points.”

—Shams Charania, NBA Insider

Lillard’s Recent Performance and Potential Celtics Fit

When healthy last season, Lillard proved why he remains one of the NBA’s best scorers. In 58 games with Milwaukee, he averaged 24.9 points, 7.1 assists, and 4.7 rebounds per game, shooting an efficient 44.8% from the field. This demonstrated his ability to contribute at a high level despite his injury history.

Had the Celtics secured Lillard’s services, he would have been sidelined for 2025-26 but poised to return as a major offensive threat the following season. His presence alongside Boston’s key players could have significantly altered the balance of power in the Eastern Conference.

What Lies Ahead for the Celtics After Missing Out

Now, Boston’s front office faces the challenge of adjusting its strategy after missing out on Lillard. While recent weeks have seen minimal movement, executives like Brad Stevens remain actively engaged in exploring alternative options to strengthen the roster. Fans and analysts await further transactions as the Celtics look to rebuild momentum in free agency and prepare for the upcoming season.