Damian Lillard Wasted Everyone's Time The Last Two Years

Damian Lillard is a Portland Trail Blazer yet again.

After two somewhat disappointing seasons in Milwaukee, which ended with him tearing his Achilles in round one of these past playoffs, Lillard last week signed with the Blazers on a three-year, $42 million deal after being stretched and waived by the Bucks earlier in the month. The deal will likely allow Lillard to retire as a Blazer as his career begins to wind down.

On the surface, it’s a nice story as a franchise legend returns to the team and city that he shares a mutual love with.

But when all these events have me thinking, what was the point of the last two years? Because, at least in my opinion, it just feels like the last two seasons wasted a lot of people's time.

After the 2022-23 season, Lillard finally demanded a trade out of Portland to try and go compete for a championship. When he made the trade demand, Lillard specifically told the Blazers he wanted a deal with the Miami Heat. However, the Trailblazers were not happy with the Heat's offers, and Lillard got sent to Milwaukee—a destination he didn’t want but one that a lot of people thought gave him an unreal chance to go win a title. On paper, Lillard and Giannis should have been a great pairing, but unfortunately, they could never really get on the same page. An aging supporting cast, injuries, and multiple disappointing coaches led to Lillard's time in Wisconsin being a disaster.

And had Dame asked to leave Portland (which I believe he never really wanted to do and just felt the pressure from the media to do so), maybe none of that happens. Maybe the Bucks aren't stuck in the less than ideal situation they are in now. Maybe Miami doesn’t spend months waiting on Portland, believing they’d land Lillard, missing out on other potential trades that summer. His decision didn’t just reroute his own path—it altered the trajectories of multiple franchises and players. Now, two years later, we’re right back where we started… And I just feel like it was all pointless.

To me it is now clear that Lillard has or never was driven by winning championships. That’s not a knock—every player is allowed to define success on their own terms. But this return confirms what many of us suspected: he was always most comfortable being the guy in Portland. The person the franchisee ran everything by.

If that’s what makes him happy, great. But from a fan perspective, it’s sad. I wanted to see Dame in deep playoff battles next to other stars. I wanted to see him on the biggest stage, not riding out his career with a young team still years away from contention.

Lillard is one of the 75 greatest players in NBA history. But this final chapter just reinforces a long-standing truth about his career: he should have left Portland years ago. He had more than enough chances to move on and chase a ring in his prime. Instead, he stayed—loyal to a fault, some might say.

There were rumours that he had interest in joining the Celtics or Warriors. Imagine Dame next to Tatum and Brown or sharing a backcourt with Steph Curry. That would have been awesome to see and would have put him in contention when he returns for the 2026-27 season.

Instead, we are getting the nostalgic ending. I don’t blame the Blazers one bit for bringing back Lillard—but I do wish Lillard had chosen differently because it just makes the last two years feel meaningless, and more people were hurt than helped over the past two NBA seasons.

And frankly? They didn’t need to happen at all.

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