This summer, just minutes after the surprising trade of Damien Lillard by the Milwaukee Bucks, speculation about his next team quickly erupted. Initial mentions included Portland and Miami—places Lillard had shown interest in before—but soon Golden State, Boston, and the Los Angeles Lakers became prominent contenders. Many expected the decision to drag on, especially as Lillard was recovering from a torn Achilles and considering his options.
However, the wait was short-lived—Lillard signed a three-year, $42 million deal to return to Portland. This season, he will earn $14 million from Portland alongside the $54.1 million from Milwaukee, totaling $68 million, though he’ll miss much of the recovery period.
Here’s a breakdown of the biggest winners and losers in this scenario—and it’s largely positive.
Winner: Trail Blazers and Basketball Fans
This outcome feels emotionally rewarding. Lillard could have chosen to wait for a bidding war or chase the highest offer, but instead, he followed his heart, choosing the city he loves and where his family resides. He joined a franchise eager to honor its legendary players like Bill Walton and Clyde Drexler, making this a fitting and heartfelt moment in sports. Blazers fans had a great summer, with the franchise now for sale and a pause on relocation talks led by Adam Silver. The team also secured promising talent through the draft, and most importantly, they have Lillard back.
Winner: Damien Lillard
While initially excited about joining Milwaukee and teaming up with Giannis Antetokounmpo to chase a championship, Lillard struggled to adapt to life away from Portland, his family, and familiar surroundings. Being released by Milwaukee gave him full control over his next move. Ultimately, Portland was his top priority, and he secured a fair mid-level contract despite being in recovery. This allows him to refocus on what matters most to him.
Winner: Portland’s Young Players
Developing young talent is crucial, and having a seasoned leader like Lillard is invaluable. Players like Scoot Henderson, Toumani Kamala, Donovan Klinge, Shedon Sharp, and Jan Hansen will benefit greatly from Lillard and Jusuf Nurkic’s presence in the locker room. This bodes well for the Blazers’ future.
Loser: Other Teams Pursuing Lillard
Although no other team won the "sweepstakes," Miami, Boston, Golden State, and the Lakers all showed serious interest. Miami viewed Lillard as a perfect fit, Boston’s Jayson Tatum personally tried to recruit him, Golden State imagined a lethal backcourt pairing with Steph Curry, and the Lakers saw him as an ideal playmaker alongside Luka Doncic. Despite strong cases from these franchises, it’s clear Lillard’s heart and home pulled him back to Portland.
Fan Take:
Damien Lillard’s return to Portland is a win for loyalty and the emotional connection between a player and his city. For basketball fans, it emphasizes that beyond championships and money, passion and belonging drive the sport’s most meaningful stories, potentially inspiring a new chapter of excitement and leadership for the Trail Blazers.
