Damian Lillard's career deserved a better 2nd act

All sports injuries are tough, but some of them feel crueler than others.

Watching Damian Lillard crumple to the floor and grab at his heel in Game 4 of his Milwaukee Bucks' first-round series against the Indiana Pacers on Sunday night, knowing what that type of noncontact injury entails, was particularly difficult to stomach. As he was helped off the court, it was hard not to think about everything that led up to that moment.

There were all those years Lillard spent trying to lift so-so Trail Blazers teams to a higher purpose, putting up some of the best offensive seasons we've ever seen from a guard and hitting some of the most iconic shots in playoff history. He did this despite never sharing the court with another All-Star teammate after LaMarcus Aldridge left in 2015.

There was the 2023 offseason when he finally decided, with his runway as an elite player shrinking, that it was time to maneuver his way to a more competitive situation.

Then there was the trade that sent him to Milwaukee, which wasn't his preferred destination but paired him with by far the best teammate he's ever had. It seemed to offer the promise of championship contention in the twilight of his prime. His first season with the Bucks was choppy, as he struggled initially to sync up with Giannis Antetokounmpo on the court, dealt with personal challenges off the court, and navigated all manner of coaching turmoil.

He still managed to put up a huge first round against Indiana, which went for naught because Antetokounmpo sat out the series. Lillard himself missed multiple games with a strain in the same Achilles tendon he'd eventually tear.

Lillard was better this season than last, and he and Antetokounmpo fine-tuned their two-man synergy. It still wasn't enough to make the Bucks championship contenders because the infrastructure around them continued to crumble. Brook Lopez, now 37, finally started to show his age. Khris Middleton couldn't stay healthy and was traded for an ineffectual Kyle Kuzma. The team's depth was nonexistent. Then Lillard developed a blood clot in late March that seemed certain to end both his season and his team's.

That he managed to return four weeks later from a condition that typically takes at least three months to fully treat was miraculous. That he did so only to suffer a career-altering injury five days later is devastating. We haven't seen the last of Lillard, but we've very likely seen the last of him as an All-Star-caliber player. He'll turn 35 this summer, and there's just no history of players his age coming back from Achilles tears and still playing like stars.

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Shooting is a resilient skill, and Lillard is one of the greatest shooters of all time. But his secret superpower has always been his driving ability, and the way he's been able to play the threat of his drive against the threat of his pull-up jumper. It's hard to imagine him being able to do that as effectively in the wake of this injury. The 2025-26 season is already a write-off. He'll be 36 when he next takes the court. Who knows what the Bucks will even look like by then.

The franchise would've been in dire straits even if Lillard had made it through the playoffs unscathed, having relinquished control of all its own first- and second-round picks through 2030 for a win-now roster that looked unlikely to escape the first round anyway. Now, Milwaukee will be allocating 82% of the salary cap to one player actually on the court.

There are no prospects in the pipeline ready to break out and pry the window back open. Lopez, who's been as foundational as anyone to the team's identity during the Giannis era, is about to become a free agent and is currently being played out of the Pacers series. It's well and truly over for this iteration of the Bucks.

Loyalty has become nearly as central to Antetokounmpo's NBA persona as it was to Lillard's in Portland, but there comes a point at which even the most steadfast superstar sees the writing on the wall. Milwaukee has zero hope of contending next season without Lillard, and not much more hope of doing so with a compromised version of him after that.

Antetokounmpo's commitment to the Bucks is admirable, and I'm usually not one to advocate for players demanding trades. But the cold reality is that any season he remains with the team from here on out will be a waste of one of the precious prime years remaining to him now that he's turned 30. And if he's looking for a cautionary tale about waiting too long to end a partnership that no longer has a future, he needn't look further than Lillard.

It sucks to say this about Lillard, a guy who was often a refreshing voice during an era of superstar nomadism; a guy who once said, "Something that's missing in our league is the character and the fight and the passion and pride about not just the name on the back, but the name on the front." At this point, though, it's hard not to feel that Lillard was cheated a bit, and that his career deserved a more dignified second act than this.

He wasn't a perfect player by any means and was sometimes the author of his own misfortune. His defensive deficiencies were part of the reason his teams were often capped with second-round ceilings. He also had some real playoff stinkers, including four straight rough showings from 2015 to 2018. But you could never lay too much blame at his feet given how thin his margin for error was.

His Blazers teams peaked with a 2019 Western Conference finals berth, but Lillard kept pouring in monster production even as they failed to win a series thereafter. He had the best playoff performance of his career in 2021, featuring the single best game score of any postseason game ever, and the Blazers still lost to the Jamal Murray-less Nuggets in the first round. Two years later, he averaged over 32 points on nearly 65% true shooting - one of five players in NBA history to score that much on that level of efficiency - and Portland didn't even sniff the play-in.

If those Blazers teams failed to live up to expectations, it was only because Lillard's unparalleled gifts as a pick-and-roll operator set the expectations higher than they should've been in the first place. He spent his prime years adding layers to his game and meticulously honing his craft, all while hoping for a championship-caliber cast of teammates that never materialized. Then, when he finally got a chance to team up with a Grade-A superstar, everything went to hell.

Here's hoping that, against the odds, there's a more heartening final chapter to his career still waiting to be written.

Joe Wolfond covers the NBA for theScore.

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