Lillard's torn Achilles is the latest, and most serious, reminder that his post-Portland chapter has not gone according to plan.
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In the days since Damian Lillard tore his left Achilles on Sunday, I've been thinking about something he said two years ago, in one of the last of the dozens of interviews he gave during his years in Portland about the dangers of leaving to chase a championship elsewhere.
The Dame Is Loyal To Portland interviews were a self-contained content vertical in those days, one that everybody—including Lillard—was tired of hearing about well before the end. They all ran together after a while: a national writer parachuting into town would ask a question he'd already answered a hundred times, and he'd give some version of a quote about how winning somewhere else wouldn't be as satisfying as doing it Portland.
But speaking to ESPN's Baxter Holmes in the spring of 2023, he got more specific than he ever had about how it could go wrong if he took the other path.
"[Y]ou look at Russell Westbrook," he said. "You leave OKC for Houston, then James [Harden] decided he's leaving, now Russ is traded to D.C., then you get traded from D.C. to the Lakers, now you're on your fourth team in four years and in your second year on the team, everybody is talking about how they should trade you. Now you're coming off the bench. This dude is a Hall of Famer, an MVP. It's an example that the grass isn't always greener."
Lillard finally asked out of Portland about four months after that interview was published, and it was hard to fault him. After being shut down, against his wishes, to help the Blazers improve their lottery odds, general manager Joe Cronin opted not to trade the pick for more veteran help to give Lillard a chance to contend, and instead drafted Scoot Henderson, who plays Lillard's position. After years of putting off making the decision, he felt the decision had been made for him. Everyone got it.
And then his second act played out as the worst version of the cautionary tale Lillard himself warned about repeatedly in those interviews. He and Giannis Antetokounmpo never meshed the way they should have, the post-trade Bucks had no depth and no assets to compete with the likes of Boston in the Eastern Conference, the hiring of Adrian Griffin as head coach was such a disaster that they replaced him with Doc Rivers midway through his first season, and the Bucks went out in six games in the first round to Indiana, in a series Lillard missed two games due to Achilles soreness.
The exact sort of organizational chaos and dead-end roster construction he left Portland to escape, he found in his new home.
(And this is where I should mention that the team Lillard wanted to go to hasn't been any more stable than the Bucks over the past year.)
It was already a minor miracle, and probably ill-advised, that Lillard was playing at all this weekend, just a month after going on blood thinners to treat a diagnosis of deep-vein thrombosis in his right calf. The injuries may not have been directly related (and were in different legs), but playing 37 minutes in his first playoff game after a month of no on-court activity can't have helped matters.
There's no point in re-litigating that now, any more than there's a point to re-litigating the handling of the trade request by Lillard or the Blazers in light of how it's turned out.
The injury supersedes all of that now, even though it already feels like it's been brushed aside in the news cycle.
On Sunday night, the tenor of much of the online discussion around Lillard's injury was that of feeling bad for a great player suffering a potentially career-threatening blow. By Monday morning, the national shows that fill up my podcast app had already moved on to where Antetokounmpo will play next year and which team has the best trade package for him.
A few of them prefaced that conversation with half-hearted apologies like "I hate that we're already talking about this after such a tragic injury, but..." before doing just that.
The NBA stops for no one, and neither does the content machine.
I don't know what the rest of Lillard's career will look like. I wish I could say with confidence that he's going to come back better than ever. The track record for players, even all-time greats, coming back from this injury in their mid-30s isn't promising.
What I do know is that Lillard wholeheartedly believes he's going to beat the odds and come back from this, just like he believed until the end that he could win in Portland. I still can't bring myself to bet against him.
The loudest Moda Center has been since Lillard left was his first game back here with the Bucks last January. The next one, probably in the 2026-27 season, could be even louder, if Lillard is able to get through what looks to be a full year of recovery.
And that could be a prelude to the final chapter in Portland that Lillard has been open about wanting since the day the trade became official in September of 2023.
His plan back then was to go get a ring in Milwaukee and then come back to Portland for a victory lap. That's off the table now.
But in two years, when Lillard is a free agent and the Blazers—maybe—are serious about contending with the group they've assembled since the trade?
Stranger things have happened.
The Rose Garden Report is a fully independent publication providing coverage of the Portland Trail Blazers you can’t get anywhere else. Purchasing a premium subscription gives you full access to all articles and ability to participate in mailbags, as well as helping to cover travel costs and other expenses to bring you the best coverage possible.
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