This Is Weird! Lillard Returns to Portland Days After Jrue Holiday Traded Back in a Stunning Full-Circle NBA Plot Twist

In what can only be described as one of the strangest and most poetic developments in recent NBA memory, the basketball universe has just experienced a full-circle moment. Damian Lillard is heading back to Portland—yes, again—just a week after Jrue Holiday, the player he was originally traded for in 2023, was dealt back to the Trail Blazers from the Boston Celtics. It’s a bizarre reversal that even the most creative NBA scriptwriters would hesitate to pitch. But it’s real. And it’s weird.

Let’s rewind to how we got here.

Back in 2023, after over a decade of loyalty to Portland, Damian Lillard was finally granted his request for a trade. It wasn’t to his preferred destination, Miami, but instead to the Milwaukee Bucks in a blockbuster three-team deal that shook the league to its core. The Bucks acquired Lillard to pair him with Giannis Antetokounmpo, forming a superstar tandem with championship intentions. To make that deal happen, Milwaukee had to part with their defensive anchor and locker room leader, Jrue Holiday.

Holiday was first routed to the Portland Trail Blazers, a move that barely lasted 48 hours. Portland, deep in a rebuilding phase, had no intention of keeping the veteran guard. He was quickly flipped to the Boston Celtics in exchange for picks and young assets, providing Boston with one of the final pieces of their championship puzzle. And as history would show, it worked. Holiday helped the Celtics win the 2024 NBA Championship, giving Boston its 18th banner and reaffirming his status as one of the league’s most elite and impactful defenders.

Lillard, meanwhile, had a much more turbulent ride in Milwaukee. Though he provided clutch shot-making and offensive firepower, injuries and chemistry issues limited the Bucks’ potential. Head coach Adrian Griffin was fired mid-season. Giannis missed time. The Bucks were ousted in the second round of the playoffs. The Lillard-Giannis experiment, while exciting on paper, never truly blossomed.

Fast forward to the 2025 offseason.

The Bucks, looking to restructure their roster under new leadership and with looming cap issues, made the shocking decision to waive Damian Lillard. The move was as much financial as it was strategic. Milwaukee needed flexibility, and Lillard’s contract was an anchor they could no longer afford to carry.

Portland, flush with cap space and still navigating a long rebuild, did the unthinkable—they reached out to Lillard.

The reunion talks gained traction quickly. Despite the messy exit just two years earlier, the bond between Lillard and the Blazers’ front office, fanbase, and city was never truly broken. And perhaps most importantly, Portland had just reacquired Jrue Holiday from Boston in a separate deal—a trade aimed at adding veteran leadership and a defensive presence to support the development of young stars like Scoot Henderson and Shaedon Sharpe.

In a matter of days, what once seemed improbable became reality. Damian Lillard cleared waivers and signed a two-year deal with the Portland Trail Blazers. Just like that, he was back in Rip City, not as a prodigal son returning in shame or desperation, but as a respected legend choosing home over uncertainty. Even more astonishing—he’s now teammates with Jrue Holiday, the very player he once replaced in Milwaukee.

NBA fans and insiders were left reeling. “You can’t make this stuff up,” one prominent analyst tweeted. “This is the NBA multiverse at work.”

To appreciate how weird this truly is, let’s break it down:

• Damian Lillard was traded away from Portland to Milwaukee for Jrue Holiday.

• Jrue Holiday was then traded from Milwaukee to Portland, and then to Boston within two days.

• Two years later, Jrue Holiday was traded back to Portland from Boston.

• A week later, Damian Lillard, waived by Milwaukee, signed back with Portland.

• Now, Lillard and Holiday are teammates.

It’s the type of timeline loop you’d expect in a Marvel movie, not NBA free agency.

The implications of this bizarre chain of events are numerous.

For the Trail Blazers, it’s a culture shift. Lillard brings back his veteran presence, leadership, and unmatched connection with the fanbase. He may no longer be at his physical peak, but his experience, basketball IQ, and respect in the locker room could prove invaluable. Jrue Holiday, too, is a consummate professional who defends at an elite level and plays with quiet confidence. Together, they’ll act as mentors for the team’s rising core of young talent.

There’s also poetic symmetry in the return. Lillard’s original exit was seen as both inevitable and heartbreaking. Fans wanted him to chase a ring, and he obliged. But now, he comes back without bitterness, without ego. There’s a mutual understanding that his legacy is Portland. No matter where he’s played, Rip City was always home.

From Milwaukee’s perspective, the story is less nostalgic and more cold-blooded. The Bucks’ decision to waive Lillard sent shockwaves, but it was a calculated one. They opted to lean into Giannis’ timeline with a revamped, more flexible roster. Whether it pays off remains to be seen. But the move further cements the NBA as a business-first league, where loyalty is often secondary to dollars and long-term planning.

As for Boston, they opted to move off Holiday following their title run. His value was sky-high, and they took the opportunity to recoup future picks and reshape their roster around Jayson Tatum and Jaylen Brown, who now have the keys to a more offensively dynamic backcourt.

For fans, the Lillard-Holiday reunion is one of those rare sports moments that feels like both a glitch in the matrix and a heartfelt ending. Two stars who were traded for one another, bounced between coasts, and forged championship-level careers, now find themselves in the same locker room. Their professional paths, once divergent, have intersected in the most unexpected of ways.

Even more intriguing is how this affects Portland’s competitiveness. While no one is penciling them in as title contenders yet, a veteran duo of Lillard and Holiday anchoring a squad full of athletic, high-ceiling prospects could make the Blazers one of the West’s most interesting teams. Add in Anfernee Simons, Deandre Ayton, and a developing Scoot Henderson, and you have a team capable of making serious noise—or at the very least, ending the perpetual lottery cycle.

More importantly, this moment serves as a reminder of how unpredictable and emotionally charged NBA careers can be. Damian Lillard never wanted to leave Portland, and Jrue Holiday never thought he’d be back. Yet, here they are—reunited in a city that’s seen both their highs and lows, ready to write a new chapter together.

And maybe that’s the weirdest part of all.

Because as strange and unexpected as this story is, it somehow feels…right.