THOUGHTS | DAMIAN LILLARD RETURNS TO PORTLAND

The prodigal son just returned home with a torn Achilles tendon and a boatload of money, and honestly, I’m loving it.

Damian Lillard could’ve been a Portland lifer. But because of the NBA’s blasted ring culture, he was forced to ask for a trade. Same thing happened with Russell Westbrook in Oklahoma City, Bradley Beal in Washington, and decades ago, with Reggie Miller in Indiana and Karl Malone in Utah.

Dame was traded to Milwaukee to form a dynamic one-two combo with former MVP Giannis Antetokounmpo. And that’s when everything started to unravel. The minute he suited up for the Bucks, he lost his superstar identity.

Suddenly, Lillard was no longer a franchise face—he was just a hired gun.

When a player spends most of his career with one team, asking for a trade comes with two choices: either go all in and make the second team your last, or become a wandering nomad with no real basketball home. Lillard, like many before him, lost his exclusivity. The team that once adored him now had to move on, and the team that got him treated him like an accessory. And when you’re replaced or forgotten, it stings. Just ask Vince Carter when he left the city with Chris Bosh and DeMar DeRozan, which led to Kawhi Leonard and Toronto's first NBA title.

Let’s run through the careers of the players I mentioned after they left their original teams.

Westbrook has played for five teams in six seasons, earned the nickname “West-brick,” and is currently struggling to find an NBA team. Beal got shipped to Phoenix, blamed for the Suns’ failures, and now finds himself in Los Angeles, essentially replacing Norman Powell. Karl Malone left Utah to chase a ring with the Lakers, only to get injured, average just over ten points, lose in the Finals again, and retire after the team lost interest in him. Vince Carter? After Toronto, he moved to New Jersey and then bounced around six other teams over 11 seasons. Nearly half of those years, he averaged fewer than 10 points per game. His late-career stints weren’t about chasing titles—they were about mentoring small-market teams. It felt more like penance than glory.

Then there’s Reggie Miller. He had chances to leave Indiana. The Celtics wanted him, but he stayed. He retired without a ring, but with something just as rare in today’s game: undying respect. He retired as a legend, a Pacers lifer, and a name on the NBA 75th Anniversary Team.

Lillard was also named to that 75 list before leaving Portland. At the time, I didn’t love the pick. Dwight Howard and Tracy McGrady had stronger résumés. Dame had no MVPs, no rings, and only one All-NBA First Team nod at the time. Yes, he had seven All-NBA selections, but Howard had eight, and five of those were First Teams.

Looking back, I still think I had a point.

Two years after the list came out, Lillard was in Milwaukee. He kept his stats up, but only played seven playoff games across two years. In his final game, he suffered a torn Achilles that ultimately doomed their playoff run. That injury didn’t just end a series—it ended his Milwaukee era. That’s what happens when you become a hired gun. You go from centerpiece to role player. You exist to complement someone else’s greatness. Whether or not Giannis had a say in his exit, Milwaukee was always going to do whatever it took to keep the man who brought them their first title since the days of Lew Alcindor and Oscar Robertson. If Dame couldn’t be the Robertson to Giannis’ Kareem, then the Bucks had to find someone who could—even if that’s just someone like Myles Turner.

At least he’s healthy.

So while it’s heartbreaking, it makes sense.

Lillard was out.

Now he’s back in Portland.

He never truly wanted to leave. Whether it was the city, the fans, his kids, or just unfinished business, something brought him home. At 35, with a three-year deal in his pocket, he’s got a chance to end things where they started. And if he ever does leave again in search of a ring—which I doubt—his return already earned him more goodwill than before.

He’ll likely return as the leader. Maybe even reclaim his superstar role. Unlike Westbrook’s OKC stint, there's a clear spot for Dame in Portland’s story. He’s not an outsider trying to fit in—he’s family.

That’s the real trap of ring culture. You’re either the guy who gets carried to a title, or you’re the one who supports the team's carry and falls short.

At this point, Dame will never be the main star of a championship team. Portland is still looking for its way to make the NBA Playoffs. At best, he’ll bounce around like Gary Payton in the twilight of his career. Sure, he could join a contender. But then what? Ray Allen joined Miami, won a ring, and then spent years stuck in retirement limbo.

Lillard’s résumé already speaks volumes: NBA 75th Anniversary Team, seven All-NBA selections, nine All-Star appearances. And now he returns to Portland to solidify his status as the team's number one all-time scorer with $42 million from his new deal and $54 million still owed by the Bucks.

Whether this move is about love, legacy, or a final payday, it seals his place in Blazers history. I’m not sure if he’s now the face of Blazermania—Bill Walton delivered the title, Clyde Drexler made two Finals—but if Dame can help spark a new era, maybe even plant the seeds for a Blazer dynasty, he just might go down as the greatest Blazer of all time.