Report: Dame reunion in Portland had people in the NBA ‘scratching their heads’

Star point guard Damian Lillard made a shocking decision as a free agent on the open market after the Milwaukee Bucks bought out his contract.

Lillard isn’t getting any younger at 35 years old and has yet to capture the NBA’s ultimate prize, yet he agreed to return to the Portland Trail Blazers — a team that seems to be far away from championship contention — on a three-year deal.

Allegedly, the Boston Celtics offered Lillard a contract before he decided to return to Portland, and signing with Boston theoretically would have given Lillard a better chance to win a title before he retires.

In light of Lillard’s decision to return to the place where he’s spent most of his NBA career, people around the league are reportedly “scratching their heads” over the reunion.

“Technically, I left Las Vegas before the Trail Blazers reached a deal to bring back franchise icon Damian Lillard on a three-year, $45 million deal, but talking to people in the league in the wake of it, this one had people scratching their heads,” The Athletic’s John Hollinger wrote.

Hollinger also floated the possibility that Portland’s move to re-sign Lillard wasn’t entirely a basketball decision.

“If you’re one of those people who likes to plot out multi-layered conspiracies with charts and arrows, there’s also plenty of room for that type of thinking,” he wrote. “Between the impending sale of the team, the Lillard move and the surprise selection of Chinese center Yang Hansen in the first round of June’s draft, a lot of the conversation in Vegas was about whether the Blazers are making purely basketball decisions right now. How much is the optics for a potential buyer influencing the basketball choices?”

While Lillard is now back with the Trail Blazers, it could be a while before he takes the floor for the first time in his second stint with the team.

After all, Lillard suffered a ruptured Achilles back in the first round of the 2025 NBA Playoffs, and the expectation is that he will miss at least part — if not all — of the coming season.

Lillard is joining a Trail Blazers team that has a lot of young talent, but it also is facing long odds to qualify for the 2026 NBA Playoffs. Portland finished as the No. 12 seed in the Western Conference last season and hasn’t qualified for the playoffs since the year 2021, when Lillard was still in his opening stint as a Trail Blazer.

Lillard is set to spend the twilight of his pro career in Portland after he had a failed stint playing alongside big man Giannis Antetokounmpo on the Bucks for two seasons.

Antetokounmpo and Lillard are two of the better players at their respective positions that the league has ever seen, yet they didn’t help the Bucks to a single playoff series victory during their time together. Milwaukee’s stints in the 2024 NBA Playoffs and 2025 NBA Playoffs both came to an end at the hands of the Indiana Pacers in the first round.