Damian Lillard Reuinion With Blazers Took Shape After GM Joe Cronin Visited

The Damian Lillard reunion with the Trail Blazers didn’t come out of nowhere. It began to take shape all the way back in his first season with the Bucks.

According to ESPN’s Jamal Collier, Lillard’s agent, Aaron Goodwin, and Portland GM Joe Cronin had a conversation in January 2024 that helped clear the air. They discussed where communication broke down during the 2023 trade saga and agreed that there was no lingering bad blood.

Lillard had pushed for a trade to the Heat that summer. But when nothing materialized by September, Goodwin told the Blazers that Lillard would stay put. Portland had other plans. With training camp approaching, Cronin sent Lillard to Milwaukee instead.

“More than anything, it was miscommunications and misunderstandings,” Lillard said, via ESPN. “Joe and I never talked about [a potential return]. It just sat out there and we let it be what it was. I think that was the mistake.”

Even when he was traded, Lillard still pictured himself finishing his career with the Blazers. And that vision came full circle, though not in the way anyone expected. After tearing his Achilles during the playoffs this past season, Lillard was waived by Milwaukee, which used the stretch provision to open up space and land free agent big man Myles Turner.

Per Collier, the Bucks had already been weighing their options with Lillard before the injury. A trade was on the table if things didn’t click, with the goal of finding another top-tier piece to pair with Giannis Antetokounmpo. But once the injury happened, the decision shifted.

Lillard returned to Portland on a three-year, $42 million deal. Cronin visited him at home to check in on his recovery and mindset. They talked about the team’s progress, the direction of the rebuild, and Lillard let it be known that he liked what he was seeing. Not long after, they made it official.

Lillard is expected to spend the entire 2025-26 season rehabbing, but there’s no doubt in his camp that he’ll be back.

“It’s Dame. I know Dame,” Goodwin said. “I know the desire. I know the fight. I know how hard he works. And I didn’t see this as anything that was going to shut down his career. It’s going to be something that maybe even prolongs his career — because he goes so hard that he’s got to give his body a break.”

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