Damian Lillard’s career is one that’s been defined by more than just stats and accolades. It’s been a journey—one that’s seen him form genuine bonds with everyone from the arena staff to the fans in the Pacific Northwest. Portland wasn’t just the city where he played; it was where he put down roots, where he felt valued for his relentless work ethic and shared a connection born of an underdog mentality.
Now, it looks like Lillard’s journey is coming full circle. After a challenging two-year stint with the Milwaukee Bucks, Lillard is heading back to the Portland Trail Blazers with a fresh three-year, $45 million contract. The deal, which includes a player option for the 2027-28 season and a no-trade clause, means Portland fans will have much to cheer about once Lillard recovers from a torn Achilles sustained during the Bucks’ playoff series against the Pacers.
Lillard’s bond with Portland and its fans is something he’s cherished. “My relationship to the city, and the fans here, the organization… It’s never-ending,” he said when he first returned to compete against the Trail Blazers in a Bucks jersey in 2023. It’s clear that Portland has always been more than just a team for Lillard; it’s been home.
He announced his return in style on Instagram, walking fans through the Blazers’ locker room before landing on his old locker, a move that was both nostalgic and symbolic. Lillard’s locker now sits adjacent to promising third-year guard Scoot Henderson. This is notable because Henderson was the catalyst for Lillard’s initial trade request; Lillard had hoped Portland would use the draft pick that landed Henderson to bring in a more seasoned player to aid in his quest for a championship. But with Henderson’s addition and veteran Jrue Holiday also in the mix, it seems potential now surrounds Lillard, who will play a dual role as both competitor and mentor.
Lillard’s departure from Portland did come with its share of tension. The relationship with management was strained, particularly with GM Joe Cronin, who had promised to build a robust team around him but then sent key players like CJ McCollum, Norm Powell, and Josh Hart elsewhere. A requested trade to Miami didn’t materialize, and instead, Lillard found himself in Milwaukee, a place that, despite talent and playoff runs, didn’t quite fill the void left by Portland.
Drafted sixth overall in 2012, Lillard didn’t take long to leave his mark in Portland. Rookie of the Year honors, seven-time All-Star—he quickly became a franchise icon. His accolades on the court include becoming the all-time franchise leader in points, 3-pointers, and free throws, while also ranking high in assists and games played. Lillard’s legacy was sealed with iconic moments like that buzzer-beater against Houston in 2014 and the 50-point game against Oklahoma City in the 2019 playoffs.
While his time at Milwaukee had its highs, including All-Star nods and playoff appearances, it also pointed out that more talent doesn’t necessarily mean more success. The absence of his family, the connection to the city, and the bond with the fans left a gap in his life—a gap Portland could uniquely fill.
With Milwaukee reshuffling and releasing Lillard to create financial flexibility, Lillard’s journey found a new chapter. His Instagram announcement from the Trail Blazers locker room resonated deeply with fans, coupled with a fitting message: Together Again. It’s a reminder that, for Lillard, this isn’t just about basketball—it’s about returning to where the journey started and where, hopefully, it leads to another electrifying chapter.
