In 2023, Damian Lillard shocked the league by leaving Portland to join the Milwaukee Bucks. Two years later, things came full circle. After being waived by the Bucks recently, Lillard returned to the Blazers. It was a bittersweet reunion. He’s back where his heart always was, but a torn Achilles suffered during the 2025 playoffs has left him sidelined indefinitely.
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Still, his presence gives Portland a much-needed morale boost. Off the court, he remains a mentor and a leader. On the court, the team has tried to move forward by adding key pieces like Jrue Holiday.
The veteran guard brings defense, playmaking, more importantly, championship experience to a young roster ready to make its mark next season. Despite the moves, ESPN’s Brian Windhorst doesn’t believe the Blazers are playoff-bound. He sees a franchise stuck between two timelines.
On one hand, they’re trying to build a young core. On the other hand, they’re bringing in experienced players like Holiday to stay competitive. That balance hasn’t worked out as hoped. To make it a little worse, Dame isn’t going to be on the floor for a long time.
On NBA Today, Windhorst said, “The organization, quite frankly, hasn’t been the same since he left. They’ve been in a rebuild. They didn’t have high expectations, but they’ve been underwhelming even in the status of their rebuild.” According to Windhorst, the only great thing for the franchise and fans is that Dame is back. But his return has very little to do with their chances in the postseason.
Windhorst said, “The way they’ve structured this deal where they’re paying him the full mid-level…I guess it’s a value next year, but this year they’ve got $40 million in dead money when you include the buyout to Deandre Ayton and what they’re paying Dame to be an assistant coach, by their own admission.”
Windhorst also couldn’t understand what was the point of signing Jrue Holiday at a time when their roster is full of young stars and their franchise cornerstone is going to sit out for a while. Windhorst thinks the uncertainty around the team’s direction for the next couple of seasons will ultimately end up forcing them to just be floating below the play-in spots.
He said, “I expect them to have good nights and bad nights this season, and I do not see them as a playoff team.” Lillard’s return is a feel-good moment. But the reality is, it doesn’t change much in terms of winning. Portland still has a long way to go before contending again.
