When Damian Lillard walked away from the Milwaukee Bucks, everyone assumed he’d chase a championship ring. Instead, “Dame Time” chose something more powerful: home. The greatest player in Portland Trail Blazers history is returning to where he built his legend, leaving NBA insiders wondering if loyalty just trumped logic.
Why Is Damian Lillard’s Return to Portland Leaving NBA Insiders Confused?
It seemed obvious Lillard wasn’t entirely comfortable in Milwaukee, and the buyout gave him the freedom to choose his next destination. His decision to return shows how much he loved Portland, just as the city loved him in return.
Back where it started ⌚️ pic.twitter.com/bqtmFjr9Lm
— Portland Trail Blazers (@trailblazers) July 19, 2025
However, Lillard’s loyalty stands out when considering that other franchises much closer to winning were available to him in free agency. On the other hand, Portland is still rebuilding and a long way from being considered a contender in the Western Conference.
NBA insider John Hollinger of The Athletic discussed Lillard’s return to Portland and revealed that while the deal makes sense from Lillard’s perspective regarding location and finances, less can be said to defend it from Portland’s point of view. The move puts the Blazers in a potentially awkward spot.
Hollinger wrote in his column that talking to people around the league following Lillard’s return to Portland had them “scratching their heads.”
The confusion centers on timeline questions. Lillard will be 36 when he returns from a torn Achilles, which is not easy to return from, especially that late in a player’s career. Will he be the same player? That much remains unknown. Plus, the Western Conference is as deep as it’s ever been.
How Does Lillard’s Contract Complicate Portland’s Rebuild?
Portland’s move muddies the waters of their rebuild since they have a very young roster, but most of their cap will be tied up with veterans Jrue Holiday, Jerami Grant, and Lillard through the 2027-28 season if all three opt into their final years.
Lillard also isn’t returning at a discount. Hollinger points out that he’ll make around “$64 million for the next two seasons,” including the stretched-out money from the Bucks over five years.
The situation becomes more complex when considering the Blazers’ roster construction. Hollinger highlights the awkward spot Portland faces, including their thin backcourt, due to the dead money paying Lillard handsomely not to play in 2025-26. Then there’s Scoot Henderson’s status as the young point guard they’ve been developing over two seasons.
If Henderson breaks out during the 2025-26 campaign, how would that work with Lillard looking to have a big year in 2026? According to Hollinger, “There are a million ways this can go wrong.”
“Lillard is a dead-money roster spot for 2025-26 and leaves the Blazers very thin in the backcourt after the Anfernee Simons trade; one presumes Portland will land a veteran point guard with its final roster spot (the Blazers can sign a veteran’s minimum contract and stay a few pennies below the tax line),” Hollinger wrote.
However, Hollinger’s concerns extend beyond just the immediate roster implications. The timing creates a potentially awkward dynamic that could complicate Portland’s development timeline.
“Lillard will come back in the fall of 2026 wanting to prove he’s that Damian Lillard, which could be problematic if Henderson emerges in 2025-26; that combined with Lillard’s status in Portland could lend itself to some Kobe-in-2016 vibes,” continued Hollinger.
Despite the questions surrounding the move, the Blazers have made a decision that instantly reinvigorates their fan base by bringing back their beloved legend. Lillard’s jaw-dropping historic feats in clutch time are etched in Blazers history forever.
No one should doubt that Lillard will want to add to that legacy now that he’s home.
