
Damian Lillard is ready to make his long-awaited return to the Portland Trail Blazers, but the nine-time NBA All-Star admits there was a point when his basketball future looked considerably less certain.
Speaking with Marc J. Spears of Andscape ahead of Portland’s October 21 season opener against the Phoenix Suns, Lillard opened up about the emotional toll of his torn Achilles tendon, his departure from the Milwaukee Bucks and the possibility of retirement.
Now 36, Lillard is cleared to play in the 2026-27 NBA season after missing the entire previous campaign. His return comes nearly 18 months after suffering the devastating injury during the 2025 NBA playoffs.
Getting back to this point was anything but guaranteed.

Damian Lillard Reveals ‘Darkest Day’ After Bucks Departure
Lillard suffered a torn left Achilles tendon on April 27, 2025, while playing for Milwaukee against the Indiana Pacers.
The Bucks subsequently waived the veteran guard, ending his two-year tenure with the organization and leaving him without a team for the first time in his professional career.
In an October 20 interview with Andscape, Lillard described the uncertainty surrounding that period.
“The darkest day was when I was hurt and got waived,” Lillard told Spears.
It was an unfamiliar situation for a player who had spent more than a decade as the face of an NBA franchise before moving to Milwaukee in pursuit of a championship.
Lillard considered spending the following season without a team, recovering from his injury and waiting until he was healthy enough to pursue another opportunity.
Instead, he returned to Portland on a three-year, $42 million contract, reuniting with the franchise that originally selected him in the 2012 NBA draft.
He also acknowledged briefly considering retirement, although that thought was driven by his desire to spend time with his children rather than concerns about his Achilles injury.

Is Damian Lillard Playing This Season?
Yes. Lillard is healthy and expected to play for the Portland Trail Blazers during the 2026-27 NBA season, beginning with Wednesday’s opener against the Suns.
He was not listed on Portland’s initial injury report and has already returned to the court during preseason action.
Lillard appeared in three preseason games, averaging 17.3 points, 2.7 assists and 1.7 rebounds.
Wednesday’s contest marks his first regular-season appearance since tearing his Achilles and his first regular-season home game for Portland since March 17, 2023.
His return follows an entire season dedicated to rehabilitation. Lillard told Spears that he deliberately avoided rushing back, wanting to regain confidence in his body before competing again.
Portland head coach Micah Nori also expressed confidence in the veteran’s recovery, explaining that Lillard’s shooting ability remains intact despite the lengthy absence.
Damian Lillard Faces New Role Alongside Ja Morant
Lillard is returning to a different Trail Blazers team than the one he left in 2023.
Portland finished 42-40 last season and reached the playoffs behind All-Star Deni Avdija. The organization has since added two-time All-Star Ja Morant, creating a crowded backcourt that also features Jrue Holiday and Scoot Henderson.
Rather than asking Lillard to orchestrate every possession, Nori intends to use him more frequently away from the ball, creating additional opportunities for the veteran to find open shots.
That adjustment could help extend Lillard’s career while allowing Morant to shoulder some of the playmaking responsibilities.
There is also a milestone within reach.
Lillard scored 19,376 points during his first stint with Portland, leaving him 624 points away from becoming the first player to score 20,000 in a Trail Blazers uniform.
After the injuries, uncertainty and a season spent watching from the sidelines, Lillard finally has another opportunity to build on that legacy.
His first chance arrives Wednesday against Phoenix, with tipoff scheduled for 10 p.m. ET.
Damian Lillard Reveals ‘Darkest Day’ of NBA Career Before Trail Blazers Return