Damian Lillard’s 2024-25 season with the Milwaukee Bucks was supposed to be his moment. Fans believed he’d be the missing piece. Hopes were high for him to be the closer who would finally push the Bucks back to the top. But instead of glory, the season brought heartbreak. A left Achilles tendon injury during Game 4 of the first round silenced his momentum, ending his playoff run. For a player who thrives on rhythm and explosiveness, it was a major setback. Without Dame, Milwaukee’s title hopes quietly collapsed.
What’s more, Lillard is set to make a staggering $141 million over the next two seasons. That includes $70 million next year as he rehabs his Achilles. The figure blends the final Bucks payouts with his new Blazers contract, ensuring financial security regardless of on‑court results. While some might call it a consolation prize, money aside, the payoff also comes with a return to familiarity. It’s a rare win-win: stability and support when he needs it most.
On The Hoop Collective, Brian Windhorst put it clearly: “He could not say no to this. Um, and I’m sure he’s happy to say yes, but he also could not say no.” Tim Bontemps added more context to that moment, saying that the past few years were tough for Lillard, not just professionally but personally. “His family was back in the Pacific Northwest. He was in Milwaukee. He’s talked at times about how tough a situation that was for him.” Being injured and away from loved ones didn’t help. Returning to Portland gives him something deeper than a fresh start; it brings back the part of him that Milwaukee never really reached.
Mar 13, 2025; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) dribbles the ball against the Los Angeles Lakers in the first quarter at Fiserv Forum. The Bucks wore a small patch to honor former player Junior Bridgeman who passed away this week. Mandatory Credit: Benny Sieu-Imagn Images
But there’s more than just sentiment behind this move. Bontemps highlighted how this could help Portland’s young core grow. “You got Jrew Holiday and Dame Lillard mentoring them,” he said, referring to Scoot Henderson’s development. Windhorst agreed, adding, “Their locker room will be spectacular. I don’t know how they’ll be on the floor, but their locker room is going to be spectacular.” And when it came to how the Bucks played a role, he said: “Dame owes a valentine to the Milwaukee Bucks organization…them cutting him when they did opened this up.”
Maybe the injury wasn’t the end; instead, it just redirected his path. It may just be that Dame will be seen back to his best back home, exactly where he initially made a name for himself.
Damian Lillard’s return brings nostalgia but leaves Portland’s true plan up in the air
Damian Lillard’s return to Portland may sound like a feel-good headline, but beneath the surface, the story gets complicated. On The Hoop Collective, Brian Windhorst gave a clear summary of the deal: “Dame Lillard is going back to the Portland Trailblazers on a two-plus-one deal. Two years plus a player option, basically at the mid-level exception, $42 million.” Though this was not entirely accurate, as the contract is actually three years total (2 guaranteed + 1 player option), not “two plus one” presented as separate.
The numbers are real, and so is the nostalgia. But what does it really mean for Portland’s future?
Tim Bontemps, speaking from Lisbon, shared the unexpected moment it all hit him. “I walked out of the room, and a few minutes later, I got a tweet from Shams announcing that this Dame thing was happening. And the first thing I thought was, ‘This is an awesome story.’” For a franchise legend to return where it all started, it does feel like a movie moment. But Portland’s broader vision remains unclear, especially after all the offseason moves they’ve made.
Bontemps also pointed out a critical part of the deal that might shape how things unfold. “Gets a no trade clause, which I think is extremely smart by Aaron Goodwin and Dame’s management team to make sure that he has some control over his future.” In a league where players are often traded overnight, this small clause gives Lillard the power to choose what happens next. Well, Bradley Beal got a payday because of it. That kind of control matters when you’ve spent years bouncing through unexpected turns.
Still, the confusion around the Bucks’ direction remains. “Now has $40 million essentially in dead money on their books for the 25-26 season. That is a very hard thing to square,” Bontemps said. Even for Portland, bringing Dame back on a team that’s supposedly rebuilding feels like a split decision. What are they aiming for? A farewell tour, a playoff push, or just buying time?
Even Bontemps admits the logic gets murky. “The Dame thing in a vacuum, honestly, totally makes sense… I just don’t really get what Portland’s trying to do in general.” Maybe fans will enjoy the nostalgia. Maybe Scoot Henderson learns from a vet. But until things click, the Trail Blazers’ playbook still reads like a puzzle without clear edges.
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