Bucks News: Damian Lillard Admits It ‘Never Felt Right’ Leaving Blazers, Reflects on Emotional Disconnect During Milwaukee Tenure

Coming right out with what many suspected but few truly knew, Damian Lillard has finally spoken about the emotional void he experienced after being traded from the Portland Trail Blazers to the Milwaukee Bucks. In a candid conversation with The Ringer, the seven-time All-Star guard admitted that while he gave his all in Milwaukee, it “never felt right” not being in a Blazers uniform — a team he had called home for over a decade.

A Jarring Departure

Lillard’s move to Milwaukee in a blockbuster three-team trade last offseason shocked the NBA landscape. The deal sent Jrue Holiday to Portland (and eventually to Boston), while the Bucks acquired a dynamic offensive force in Lillard to pair with two-time MVP Giannis Antetokounmpo. On paper, the trade was a win for Milwaukee’s title aspirations, and Lillard himself initially expressed excitement about competing for a championship.

But as the months unfolded, the emotional toll of leaving Portland — the city where he built his identity, led dramatic playoff runs, and became the face of a franchise — began to surface.

“When you’re somewhere for 11 years, and it’s all you’ve ever known, there’s a part of you that doesn’t fully let go,” Lillard said. “Even when I was in Milwaukee — with great teammates, great fans, great support — it never felt like my story. Portland still felt like home.”

Loyalty and Legacy

Lillard’s loyalty to the Trail Blazers was the stuff of legend. In an era where star players frequently switch teams in search of rings, Lillard remained steadfast in his commitment to Portland — even as the franchise failed to surround him with the roster needed for deep playoff success.

“I always said I wanted to win in Portland. That was real to me,” Lillard emphasized. “When it didn’t happen, and the front office decided to go in a different direction, I understood. But that doesn’t mean I stopped loving that place.”

That deep-rooted connection with Portland made the move to Milwaukee feel transactional, no matter how high the stakes were.

A Strained Fit in Milwaukee

Although Lillard and Antetokounmpo were touted as a super-duo capable of dominating the Eastern Conference, their chemistry on the court often looked uneven. The Bucks underwent significant growing pains, especially after the midseason firing of head coach Adrian Griffin and the hiring of Doc Rivers.

“Basketball-wise, I had to adjust a lot,” Lillard said. “In Portland, the ball was in my hands 95% of the time. In Milwaukee, I had to figure out how to be effective off the ball, and it wasn’t always natural.”

Lillard averaged 24.3 points and 6.8 assists in his first season with Milwaukee — solid numbers, but a noticeable dip from his Portland prime. More importantly, the Bucks’ offense often stalled in late-game situations, with Lillard and Giannis struggling to find rhythm in crunch time.

“When things didn’t click right away, I started questioning whether this was ever going to feel right, not just work on paper,” he admitted.

Playoff Disappointment and Reflection

The Bucks’ 2025 playoff run ended earlier than expected, with a second-round exit at the hands of the upstart Orlando Magic. Lillard missed key games due to injury, and even when healthy, looked far from his usual clutch self.

After the loss, speculation swirled about Lillard’s happiness in Milwaukee. Rumors emerged that he had lingering regrets about the trade. Until now, Lillard had been largely quiet about those emotions.

“I didn’t want to say anything during the season. I wanted to be respectful,” he said. “But once the season ended, I had to be honest with myself and admit that something felt off.”

That honesty has sparked renewed conversations around whether Lillard and the Bucks are truly built to last — or if another move could be on the horizon.

What This Means for the Bucks

For the Milwaukee Bucks, Lillard’s comments serve as both a warning and a wake-up call. The team pushed all its chips in to acquire the superstar guard, and while the pairing brought flashes of brilliance, it never fully delivered on the promise of instant dominance.

Team sources say the Bucks are aware of Lillard’s sentiments and remain committed to finding ways to improve the fit between him and Antetokounmpo. That could mean adjusting the offensive system under Doc Rivers, seeking out additional spacing and playmaking in free agency, or even reexamining leadership roles within the team.

“Dame’s not a malcontent,” one team executive told The Athletic. “He’s a professional. But he’s also human. We’ve got to make sure he feels like he belongs here — not just on the court, but in the story we’re trying to write.”

Fans React to Lillard’s Comments

Predictably, fans from both Milwaukee and Portland had strong reactions to Lillard’s remarks.

Blazers fans mostly responded with empathy, thanking Lillard for his candor and reaffirming their love for a player many still consider the greatest in franchise history.

“He’ll always be Dame Time to us,” one Portland fan tweeted. “Whether he retires in Milwaukee or not, we know where his heart is.”

Meanwhile, some Bucks fans expressed concern that their star guard might already be emotionally checked out.

“It’s hard to build a contender around a guy who’s got one foot still in another city,” one fan posted. “We need players who want to be here.”

Still, others defended Lillard, pointing to the emotional complexity of leaving a long-time home.

“He’s allowed to miss Portland,” another user wrote. “That doesn’t mean he’s not giving his all to the Bucks. Let the man grieve.”

A Path Forward?

Despite his emotional reflections, Lillard stopped short of demanding a trade or suggesting he’s unhappy in Milwaukee long-term.

“I’m here now. I’m going to do everything I can to make it work,” he said. “But part of that process is being honest — with myself and with the people around me.”

That honesty could prove to be a catalyst for a more authentic, transparent approach to leadership — one that might actually strengthen the Bucks’ locker room rather than divide it.

“I think people sometimes mistake vulnerability for weakness,” Lillard concluded. “But I’ve always believed being real about how you feel is what makes you stronger — not just as a player, but as a man.”

Damian Lillard’s comments won’t sit well with everyone — particularly in a results-driven league where loyalty is often secondary to rings. But in an NBA culture that increasingly values brand over bond, his openness about what it means to leave behind something you love is a refreshing reminder of the human side of professional sports.

For Milwaukee, the challenge is clear: turn that emotional disconnect into renewed purpose. Because if they can make Lillard feel like Milwaukee is home, not just a stop on the path to a title, they might just unlock the version of Dame that makes “Dame Time” a postseason reality once again.

Until then, Lillard’s heart will remain in Portland — even as his jersey reads Milwaukee.