PORTLAND, OR - MARCH 19: Damian Lillard #0 of the Portland Trail Blazers looks on during the game on March 19, 2023 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by Sam Forencich/NBAE via Getty Images)
Portland Brings Back Damian Lillard—But For What?
In one of the most surprising twists of the 2025 NBA offseason, Damian Lillard is returning to the team that drafted him—the Portland Trail Blazers. After two seasons with the Milwaukee Bucks, Lillard is back in Rip City, but the move raises a bigger question: What is Portland actually trying to do?
Two Years, One Letdown in Milwaukee
When Lillard was traded to Milwaukee in 2023, the goal was clear: chase a championship. The pairing with Giannis Antetokounmpo was promising on paper, but it never reached full potential. The Bucks failed to make the NBA Finals in either season, and injuries, locker room tension, and coaching instability disrupted the team’s attempts to establish a rhythm.
Now at 35 years old and a 9-time NBA All-Star, Lillard returns to a franchise that once committed to a rebuild without him. The timing feels poetic, but also perplexing.
A Conflicted Franchise Identity
Portland has spent the last two years focusing on developing young talent, such as Scoot Henderson. Now, with Lillard back and veteran guard Jrue Holiday also recently acquired, it’s unclear if this front office is pivoting toward winning or simply struggling to commit to a long-term plan.
GM Joe Cronin’s moves suggest a desire to compete sooner than expected—but without additional roster upgrades, it’s hard to envision Portland being a serious playoff threat in the Western Conference.
Loyalty or Legacy?
There’s no questioning Lillard’s loyalty—he’s always been about Portland. But this second stint must be more than a feel-good story. If the organization can’t give him a real chance to win, it risks not only wasting the twilight of his career but also muddying the legacy he built in his prime.
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