Nobody’s luck has been challenging quite like Damian Lillard’s. Just as his game reached peak form again, fate struck cruelly when a torn left Achilles tendon silenced his playoff run against Indiana. Lillard, long known for pointing to his wrist in crunch time, suddenly found himself pointing only to recovery. The heartbreak deepened when, in early July, the Milwaukee Bucks, the very team he hoped to win with, waived him. Now, as the dust settles and a major update looms, his career faces yet another crucial update.

The Bucks waived him, stretching his massive deal, which opened the door for Portland’s surprise reunion. Lillard signed a three-year contract worth $42 million, returning to the franchise where he built his legacy. Yet even with that excitement, will Rip City see him back this season, or must they keep waiting? During a recent interview on The Sideline with Andy Katz, the guard opened up about his progress. Katz asked directly about his rehab status, and Lillard kept it honest.

“It’s been moving along really well. Like I had surgery, I jumped right into the things that they allowed me to do.” He explained that he refuses to let fear control his comeback. Instead, he balances caution with steady work, showing fans that his approach is methodical rather than rushed. What encouraged fans most was hearing how far he has already come. Lillard admitted, “I recently started back running, and I’m four months out. So I’m feeling strong. I’m feeling good about it.”

Still, Lillard stressed that rushing back is not an option. He wants to heal fully, rebuild strength, and ensure that when he returns, he does so as himself, not a diminished version. His determination revealed both patience and confidence in what lies ahead. The conversation also touched on the bigger picture: why are Achilles injuries becoming so common?

Lillard pointed to the modern NBA’s demands. “Honestly, I think it might have something to do with the pace of the game. The game is getting super fast, and you’re dealing with like extremely high level athletes.” With nonstop travel, training, and physical strain, he believes today’s style pushes bodies to breaking points. For him, recovery is not only personal but a symbol of a league-wide concern.

Damian Lillard’s injury troubles trace back heavily to 2021, when he was sidelined multiple times with abdominal issues, ankle sprains, and other nagging setbacks. Those problems carried into 2022, where the abdominal strain became more persistent, forcing him to miss extended stretches. The following seasons brought more of the same calf strains, hamstring tightness, and occasional ankle sprains in both 2023 and 2024, which disrupted his rhythm even when he managed to stay on the floor. But now, as he works toward a comeback, the hope for both Lillard and Portland is simple: a full season of health from the time he joins.

Damian Lillard explains why it’s easier to make it to the NBA today

Nine-time All-Star Damian Lillard knows what it takes to carve out a long career. Entering the NBA in 2012, he came in before social media truly dominated the scouting process. But reflecting on the league now, he sees how much the game has changed. During this appearance, Lillard shared a fascinating perspective: “I don’t even think that’s a thing anymore,” he said when asked about needing to attend powerhouse schools like Duke or North Carolina.

Lillard explained that exposure has shifted. “I was sixth overall 13 years ago. So the way that social media has grown, and the way mid-majors have kind of blossomed, you’re starting to see a lot of mid-major players become the stars in the NBA.” For him, the pathway is no longer limited by school names or conference size. It is about visibility. If you can play, highlights will find you, and scouts will not ignore it.

To make his point clear, he brought up examples. Kawhi Leonard thrived at San Diego State, and Stephen Curry transformed Davidson into a household name. Lillard noted, “It wasn’t very common. They would find these guys, but I think it’s even more common now.” Social media gives every player a platform, shrinking the gap between big schools and smaller programs. Talent can’t hide anymore, and he sees that as a double-edged sword.

The growth of digital scouting has its consequences, too. “It’s as easy as it’s ever been to make it… And because of that, it’s harder for guys to stay,” Lillard added. His observation echoes Adam Silver’s idea of the NBA becoming a “highlight sport.” While easier entry now exists, surviving the grind remains as difficult as ever. Longevity, Lillard’s own career proves, requires more than just going viral.