Blazers GM Joe Cronin Admits He Didn’t Enjoy Watching Damian Lillard in a Bucks Jersey, Pleased to Bring Him Back Home

For nearly a decade, Damian Lillard was the face of the Portland Trail Blazers — an unwavering force of loyalty, clutch brilliance, and cultural relevance. So when the superstar guard was traded to the Milwaukee Bucks in September 2023, it wasn’t just a basketball transaction; it marked the end of an era in Rip City.

Less than a year later, however, Lillard is back. In one of the most surprising moves of the 2025 NBA offseason, the Trail Blazers orchestrated a blockbuster trade with the Bucks that brought the seven-time All-Star back to Portland. And for general manager Joe Cronin, the reunion was more than professional—it was deeply personal.

In a candid press conference on Monday, Cronin shared his emotions about Lillard’s time in Milwaukee and what it means to have him return home.

“I’m not going to lie. Watching Dame in a Bucks jersey didn’t feel right,” Cronin admitted. “I’ve always respected the decision we made at the time, but seeing him hit big shots for another team — especially in another jersey — it stung. It just didn’t sit well with me.”

Cronin, who had been part of the Blazers front office for over a decade before taking the reins as GM in 2021, had a front-row seat to Lillard’s rise from Weber State standout to one of the league’s most iconic stars. The two built a strong professional rapport, and the decision to trade Lillard was one of the most difficult in franchise history.

The 2023 Departure: Why It Happened

When Lillard was dealt to Milwaukee in a three-team trade also involving Phoenix, it was portrayed as a fresh start for both parties. Lillard was seeking a championship opportunity, and the Blazers were committing to a youth movement centered around promising guard Scoot Henderson.

Despite Lillard publicly requesting a trade to the Miami Heat, Cronin remained firm in maximizing the franchise’s return, ultimately accepting an offer from the Bucks that included Jrue Holiday (later flipped to Boston), draft picks, and young assets.

At the time, Cronin called it “the best decision for everyone involved.” But that didn’t mean it was easy.

“There were no hard feelings,” Cronin reiterated on Monday. “We worked with Dame to find a situation that made sense. But emotionally, it was hard seeing him go.”

Lillard’s Time in Milwaukee

Lillard’s first and only season with the Bucks was a mix of highs and frustrations. He averaged 23.7 points and 6.1 assists per game, helping lead Milwaukee to a strong regular-season finish. But chemistry issues, a midseason coaching change, and Giannis Antetokounmpo’s injuries derailed the Bucks in the playoffs, where they suffered a shocking first-round exit.

Though Lillard remained professional, reports surfaced that he never fully acclimated to life in Milwaukee — both on and off the court. His fiery on-court leadership sometimes clashed with a more reserved team culture, and the fit alongside Giannis was never seamless.

Speculation about a possible return to Portland began brewing even before the postseason ended. According to league sources, Lillard maintained communication with Blazers players and staff throughout the season, and the idea of a reunion took shape once it became clear that both sides had a mutual interest.

The Trade That Brought Dame Home

The deal that facilitated Lillard’s return to Portland was orchestrated swiftly after free agency opened in July. Portland sent a package centered around veteran guard Malcolm Brogdon, a 2026 first-round pick, and rights to international prospect Vasilije Micić in exchange for Lillard.

Though the trade raised eyebrows — especially given how much the Bucks gave up to acquire Lillard just a year earlier — Cronin defended the value and emphasized the symbolic importance of the move.

“We’re getting a player who still impacts winning at the highest level, and more importantly, someone who embodies everything the Blazers stand for,” Cronin said. “This isn’t just about sentiment. Dame is still that guy.”

The Locker Room Impact

Lillard’s return brings more than just on-court production; it brings leadership, identity, and stability. For a young team still figuring out its trajectory, having a proven veteran who is also a cultural cornerstone can accelerate growth.

Second-year guard Scoot Henderson, widely seen as the Blazers’ future at the position, publicly welcomed Lillard’s return and said he’s excited to learn directly from a player he grew up idolizing.

“Dame coming back? That’s family,” Henderson said. “He’s a legend around here. I’m just trying to soak up everything I can.”

Veteran forward Jerami Grant echoed the sentiment: “Dame sets the tone. Always has. Having him back is huge for all of us.”

Rebuilding with Lillard — Again

While the return is filled with nostalgia and emotion, the business of basketball remains. The Blazers are not immediate title contenders, even with Lillard in the fold. But Cronin believes the team can be competitive while developing its young core.

“We’re not mortgaging our future. We’re enhancing it,” Cronin said. “Dame makes us better, and the players around him now are better than what we had two years ago. The timeline isn’t as misaligned as people might think.”

Portland’s front office is reportedly exploring additional moves to surround Lillard with complementary pieces — including stretch forwards and veteran wings who can space the floor and defend. The organization is also eyeing potential buyout candidates who could join midseason.

Lillard’s Reaction to the Return

For his part, Lillard has been gracious, measured, and grateful.

“It’s good to be home,” Lillard said during his re-introductory press conference. “I went on a journey, tried something new, but this is where my heart is. I appreciate the Bucks for the opportunity, but Rip City is family.”

He dismissed questions about regret and instead focused on what lies ahead.

“I don’t look at last year as a mistake. I grew, I learned, I saw the game from a different perspective,” Lillard said. “Now, I bring all that back to Portland.”

The Road Ahead

What does this all mean for the Blazers? In the short term, a renewed sense of hope and excitement. Ticket sales have reportedly spiked, social media engagement is booming, and merchandise featuring Lillard’s No. 0 is once again flying off shelves.

In the long term, it may give the team a chance to find a balanced rebuild — one that doesn’t require sacrificing all competitive aspirations. With Lillard, Henderson, Anfernee Simons, Shaedon Sharpe, and a promising frontcourt led by Deandre Ayton, Portland suddenly looks like a dangerous wild card in the Western Conference.

“We’re not putting a ceiling on ourselves,” Cronin said. “This is a new chapter, and Dame is a big part of that story.”

Joe Cronin’s admission that he didn’t enjoy watching Lillard in another jersey speaks to more than just personal preference. It reflects a franchise identity intertwined with a player who has consistently represented loyalty, toughness, and community.

Bringing Damian Lillard back isn’t just a feel-good story — it’s a strategic pivot that aligns with both fan expectations and basketball development. And for Cronin, it’s a full-circle moment.

“There are very few players who define an organization the way Dame has,” Cronin said. “Seeing him back in a Blazers jersey feels right. It feels like home.”