Damian Lillard Gets Candid About How Relationship With Blazers GM Fell Apart

Damian Lillard rejoining the Portland Trail Blazers in free agency was certainly not on anyone's bingo card when the calendar flipped over to 2025.

And yet, here we are.

More Portland Trail Blazers News: Blazers' Yang Hansen Reacts to Damian Lillard Return

On Monday, Lillard sat with recently-extended team president Joe Cronin and recently-extended head coach Chauncey Billups at a "reintroductory" presser, and unpacked his surprising decision to re-sign with Portland.

pic.twitter.com/q46P8ucV4b
— Sean Highkin (@highkin) July 22, 2025

Per Sean Highkin of The Rose Garden Report, Lillard acknowledged that his relationship with Cronin collapsed during his last season with the Trail Blazers, 2022-23, after which he demanded to be traded to a contender.

Cronin granted Lillard his request after 11 loyal years of service, shipping him off to the Milwaukee Bucks. With two years and $112.6 million left on his maximum-salaried contract, the 35-year-old vet was stretched-and-waived by Milwaukee this summer.

More Portland Trail Blazers News: Blazers' Yang Hansen Already Drawing Attention of Rival Coaches and Executives

Thanks to an Achilles tendon tear suffered during the playoffs, it is unlikely the 6-foot-2 Weber State product will even be available to the Trail Blazers in 2025-26.

Damian Lillard on his relationship with Joe Cronin: "Toward the end, it was a lot of misunderstandings and miscommunications. When that happens, feelings are hurt. Joe and I never sat down and talked about that. We let it be and it sat out there. That was the mistake."
— Sean Highkin (@highkin) July 22, 2025

"Toward the end, it was a lot of misunderstandings and miscommunications," Lillard said of his crumbling relationship with Cronin. "When that happens, feelings are hurt. Joe and I never sat down and talked about that. We let it be and it sat out there. That was the mistake."

Clearly, they buried the hatchet. They were all smiles on Monday night, anyway.

Lillard inked a three-season, $42 million free agent contract to return to Portland following the Bucks' decision on his deal.

Portland hasn't made the playoffs at all since hiring Billups ahead of the 2021-22 season. Part of the problem to this point has been roster construction, but the Trail Blazers appear to be trending in a positive direction.

The biggest young assets have arrived in the frontcourt, with constant triple-double threat Deni Avdija seemingly unlocking something during the second half of last season and his fellow forward Toumani Camara evolving into an All-Defensive Teamer just two years into his career. Young center Donovan Clingan and rookie Yang Hansen will battle for minutes at the position, along with Robert Williams III — if Williams is ever healthy enough to play.

Portland also traded starting point guard Anfernee Simons for some 3-and-D depth, adding six-tim All-Defensive Team guard Jrue Holiday in a blockbuster deal with the Boston Celtics. Young backcourt pieces Shaedon Sharpe and Scoot Henderson will jockey for minutes alongside Holiday as they continue to develop.

Last year's Trail Blazers finished with a semi-respectable 36-46 record and barely missed the play-in tournament cutoff. Even with Lillard watching from the bench, the 2025-26 model could conceivably crash the postseason party.

More Portland Trail Blazers News:

Damian Lillard Signing With Blazers in Blockbuster $42 Million Signing

NBA Commissioner Adam Silver Discusses Blazers Relocating From Portland

For more news and notes on the Portland Trail Blazers, visit Portland Trail Blazers on SI.