Now what?

That’s what Damian Lillard must be thinking after tearing his achilles tendon in Game 4 of their first round playoff series with Indiana just more than two weeks ago.

At this point I feel like I may have beaten this into the ground, but with every figurative step that the former Trail Blazer great has made since leaving the Rose City for Milwaukee, there seems to be two steps back.

Last year it was Giannis Antetokounmpo’s injury prior to the playoffs; this year it was Lillard’s blood clot that kept him out for the last handful of weeks of the regular season; now, it’s the catastrophic injury that cost him not only the remainder of this year’s playoffs, but in all likelihood the bulk of, if not all of next season as well.

That’s bad luck, but more than that, maybe a sign that it’s time for Portland’s favorite son to come home.

On paper, it seems like a difficult, if not impossible task. With Lillard set to make more than $100 million over the remaining two years of his contract, what team in their right mind would trade anything of consequence for a player on the back nine of his career, rehabbing from one of the sport’s most impactful injuries, and who likely won’t be available until the start of the 2026-27 season?

Additionally, Portland’s post-Damian roster is built around a trio of young guards, leaving little room for an aging superstar who’s at his best with the ball in his hands.

But in a hypothetical existence, one where two plus two doesn’t always equal four, money doesn’t rule the world, and good guys in fact don’t finish last, the Bucks buy Lillard out, he becomes a free agent, and the all-star guard rides back into town to a team and city waiting with open arms.

Sound good? I think so, and I’d be willing to bet you a dollar or two that Lillard would agree.

His family is here, as is his home, and by all accounts so is his heart which the city and fanbase stole over his 11 seasons in Rip City.

That’s not a knock on Milwaukee, but rather an ode to what was, along with what could be for a player with little to nothing left to prove.

Lillard is a nine-time NBA All-Star; has earned All-NBA honors seven times; has an All-Star MVP to his name; was the league’s Rookie of the Year in 2013; and in 2018-19 took a marginal Blazers team to the Western Conference Finals. And while, yes, his resume lacks the championship he and most in the league clearly covet, it remains one that the bulk of NBA players past and present would give much for.

So, with that in mind, if you’re Lillard, why not finish your career where it started and amongst the people you built it with, rather than end it trying to catch something that might not mean much if you do?

After-all, what would a title in Milwaukee really mean? Or in Miami? Houston? God forbid, with the Lakers? Or anywhere else not named Portland where you left the blood, sweat and tears from your more than a decade-long venture to win? I think Lillard would tell you “much,” but certainly not nearly as much as it would if it culminated with a parade down Broadway in front of the countless fans who called you their own.

The Bucks are in a tough spot. They’re on the cusp of a rebuild and with Giannis potentially on his way out, it makes little sense in a post-Antetokounmpo world to keep an injured, aging, expensive and likely disgruntled superstar on a team starting from scratch. So, I say make Lillard to Portland happen.

Come to a financial agreement to send him on his way, and reunite the guard with the city and people he begrudgingly left behind.

I know, I’m just dreaming. But I like my dream over Damian’s two-year nightmare – and I’m guessing he’d agree.