Nov 26, 2023; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) shoots against Portland Trail Blazers guard Malcolm Brogdon (11) during the first quarter at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images Jeff Hanisch-Imagn Images

Blazers Insider Pours Cold Water on Damian Lillard Reunion Reports

Originally posted on Portland Trail Blazers on SI
By Ryan Stano | Last updated Jul 2, 2025 1:34 PM ET

The Portland Trail Blazers decided to trade Damian Lillard before last season as they were trying to rebuild. In doing so, they assumed that they were ending the Damian Lillard era.

Surprisingly, the Milwaukee Bucks decided to waive Lillard in order to make cap room to sign Myles Turner. Now, Lillard is free to sign with any team.

Some Blazers fans have been wondering if Lillard could be persuaded to return home to Portland. It's where he has spent the bulk of his career. Unfortunately, that doesn't look likely.

Portland would be a better team in a couple of years if they were able to bring Lillard back, but it doesn't look like that is going to happen.

Dame has openly been telling people since the day of the trade that he wants to end his career in Portland and I think he probably will, especially now that he and Cronin appear to be cool again. But it doesn't make sense at all right now, for him or for where the team is at.
— Sean Highkin (@highkin) July 1, 2025

Lillard clearly wants to end his career in Portland, but he also thinks he can still contribute to a title-contending team when he comes back from his Achilles tear.

Portland is clearly not in a position to contend for a title in either of the next two years. They still need to rebuild the rest of the roster in order to have any shot of getting into that kind of contention.

Right now, the Trail Blazers are just looking to make the playoffs, something they failed to do this season. They tried to make a push at the end of the year to make the play-in.

They fell just short, and that is why Lillard is not going to be in Portland. At this point in his career, he wants to have a shot at winning a ring. He has never won a championship.

While Lillard might end up in Portland when his career comes to a close, that might not happen until he figures out just how good he is coming off the Achilles tear.

When Lillard is able to learn what he can do after the injury, he might head back to Portland for a final year before calling it quits. That will not happen in either of the next two seasons.

This season, Lillard averaged 24.9 points, 4.7 rebounds, and 7.1 assists per game.

More Portland Trail Blazers news: Blazers’ Latest Offseason Move Has Major Financial Ramifications

Blazers Could Bring Back Damian Lillard in Shocking Move Following Bucks Release

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This article first appeared on Portland Trail Blazers on SI and was syndicated with permission.

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