If you walked through Pioneer Courthouse Square in downtown Portland back in September 2025, you would’ve seen something that felt like a glitch in the Matrix. Or a dream. Thousands of people in "Rip City" jerseys were screaming for a guy who, just two years prior, had basically broken the city's heart by asking for a divorce.
Damian Lillard was back.
He didn't just come back for a jersey retirement or a standing ovation as a visitor. He signed a three-year deal to actually be a Portland Trail Blazer again. Honestly, in a league where stars move around like chess pieces on a board, this felt different. It felt human. It was a 35-year-old superstar choosing home over chasing rings in places that didn't know his middle name.
The Trade That Wasn't Supposed to End Like This
Let's be real: the 2023 trade to the Milwaukee Bucks was messy. It wasn't the "clean break" everyone hoped for. Dame wanted Miami. Portland’s GM, Joe Cronin, wanted the best package, which ended up being a three-team blockbuster involving the Suns and Bucks.
When the dust settled, Lillard was in a Bucks jersey next to Giannis Antetokounmpo. Portland got Deandre Ayton, some picks, and a future that looked pretty bleak without "The Letter O."
But the Milwaukee experiment was... weird. There was that weird Achilles injury. Then the blood clot scare. By the time 2025 rolled around, the Bucks were heading for a rebuild of their own, and they did the unthinkable: they waived him.
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Most people figured he’d ring-chase. Maybe go to Philly? Back to the Heat? Instead, he came home.
Why the Damian Lillard Trail Blazers Connection Never Actually Broke
It’s easy to look at stats and say, "Yeah, he's the all-time leading scorer." That's true. He finished his first stint with 19,376 points, passing the legendary Clyde Drexler. But that doesn't explain why a fan named Gina Shaddox spent three months knitting a sweater with his face on it just for a rally.
The bond between Damian Lillard and the Trail Blazers isn't built on 30-foot step-backs. Well, not only those. It’s built on things like the "RESPECT" campaign he started as a rookie in 2013. He didn't just put his name on a poster; he visited schools every year to talk about bullying. He’s been a Special Olympics Ambassador since he was 17.
Most NBA players live in the city they play in. Dame lives in Portland. His kids go to school there. He owns a Toyota dealership in McMinnville. When he left for Milwaukee, he didn't sell his house. He basically just went on a long, slightly depressing business trip.
The Moments That Immortality is Made Of
If you're a Blazers fan, you have these burned into your retinas:
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- The Rockets Series (2014): 0.9 seconds on the clock. The first series win in 14 years. "Rip City!" into the microphone.
- The Wave (2019): Paul George is a great defender, but 37 feet is 37 feet. Dame hitting that shot and then literally waving goodbye to the Oklahoma City Thunder is the peak of NBA "disrespect."
- The 71-Point Night: February 2023 against Houston. He was 32 years old and looked like he was playing a video game on easy mode. 13 threes.
People forget that Dame wasn't some hyped-up prodigy. He came out of Weber State. Not Duke. Not Kentucky. He was the sixth pick in 2012, and he played like he had a permanent chip on his shoulder because of it.
What the 2026 Season Actually Looks Like
Right now, things are a bit bittersweet. The Trail Blazers are in a weird spot. They’ve got young talent like Scoot Henderson and Shaedon Sharpe, and then they have the "Old Guard" returnee.
Unfortunately, Lillard won't be hitting any deep threes for a while. That Achilles injury from his Bucks days is still the boss. The team announced in late 2025 that he's out for the 2025-26 season. It sucks.
But talk to the people in the locker room. They don't care that he's in a walking boot. They call him a "player-coach." He's there every day mentoring the guys who were in middle school when he was hitting that shot over the Rockets.
There's also the new ownership. Tom Dundon bought the team for $4 billion from the Paul Allen estate. Usually, new owners want to tear everything down and start over. But Dundon leaned into the nostalgia. Bringing Dame back was a business move, sure—it sells jerseys and tickets—but it was also a "culture" move.
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The Nuance of the "Loyalty" Debate
You can't talk about Damian Lillard and the Trail Blazers without the L-word. Loyalty.
Some critics say he stayed too long and wasted his prime. Others say he "folded" when he finally asked out in 2023. Honestly? Both can be true.
The NBA is a business, and sometimes that business is cold. Look at Jrue Holiday—the Bucks traded him for Dame without a second thought, and Jrue had just said he wanted to retire there. Dame saw that. He realized that if he didn't look out for himself, nobody would.
But coming back in 2025 changed the narrative. It proved that the "Loyalty" wasn't a marketing slogan. It was real. He could have finished his career anywhere. He chose a rebuilding team in the Pacific Northwest that might not even make the play-in tournament this year.
Actionable Insights for Fans and Collectors
If you're following this saga or looking to invest in Rip City history, here’s how to navigate the "Lillard 2.0" era:
- Watch the "Mentor" Effect: Keep an eye on Scoot Henderson’s shooting splits and decision-making this season. Having Lillard in his ear during film sessions is worth more than any assistant coach.
- Jersey Transitions: If you're looking for memorabilia, the "Return" jerseys (specifically the 2025-26 season) are already becoming collector's items because he isn't actually playing in them yet.
- Stadium News: Keep an ear out for the "Rip City Forever" group. There is a massive push for a new stadium in Portland, and Lillard is heavily involved in those community discussions.
- Health Milestones: For those tracking his return to the court, the focus is currently on his 2026-27 "Farewell Tour" eligibility. The rehab process is slow, but the goal is for him to be 100% for one final run.
The story of the Damian Lillard Trail Blazers connection isn't finished. It just has a very long intermission. Whether he ever wins a ring in Portland doesn't seem to matter as much as it used to. He’s already won the city, and in 2026, that seems to be enough for both sides.