Blazers News: Insider Provides Bold Take on Damian Lillard Signing

The Portland Trail Blazers shocked the world this summer when they decided to re-sign former superstar point guard Damian Lillard to a three-year, $41.6 million free agent deal.

The 35-year-old Weber State product's tenure out of town lasted just two years.

After missing the playoffs for two straight seasons while playing with an ill-fitting Portland roster, Lillard demanded to be dealt away from the only NBA team he had ever known in the summer of 2023.

Although Lillard preferred to join the Miami Heat, then fresh off their second NBA Finals appearance in four years, he was ultimately dealt to the Milwaukee Bucks instead.

That wasn't a terrible proposition, on paper at least. Lillard joined a club that at the time was just two years removed from winning it all, and would be playing alongside two-time MVP power forward Giannis Antetokounmpo and three-time All-Star small forward Khris Middleton.

Key championship contributors Brook Lopez, Bobby Portis and Pat Connaughton were all still on the roster at the time.

Sadly, Lillard had little luck. He was hurt during the playoffs in each of the past two seasons, and the Bucks ultimately were booted out of the first round by the Indiana Pacers in both instances.

This spring proved particularly devastating. After rushing a return from a scary blood clot issue, he wound up tearing his Achilles tendon. The Bucks opted to stretch and waive the $112.6 million that had been remaining on the final two years of his deal. Now, Milwaukee will pay him $22.5 million annually not to play for the team.

Lillard will face little pressure to return before the end of the 2025-26 season on a generally young, non-contending team with maybe play-in tournament upside. He also has a player option on the final year of his contract, meaning if he plays like even his Bucks-era self in 2026-27 (a bit of a step down from his Trail Blazers-era self), he could get a far bigger new contract in unrestricted free agency next year.

David Aldridge of The Athletic considers the move to be a rare "win-win" for Portland, noting that he can help guide former No. 3 pick Scoot Henderson as sort of a supplemental coach while he recovers this year.

"Whether or not Lillard, who tore his Achilles in April, plays a second this season for the Blazers doesn’t matter; this is a win-win, with Lillard again being able to mentor Scoot Henderson while getting a year to rehab in familiar environs," Aldridge writes.

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