The seeds for Damian Lillard‘s reunion with the Trail Blazers were planted during his first season with the Bucks, as ESPN’s Jamal Collier details.
His agent, Aaron Goodwin, and Portland GM Joe Cronin spoke in January 2024. During that conversation, they identified the gaps in their communication and agreed there were no hard feelings between the parties.
Lillard requested a trade to the Heat in the summer of 2023. When that trade failed to materialize by September, Goodwin told the Blazers that Lillard would stay in Portland. However, the front office wanted to resolve the situation by training camp and traded him to Milwaukee.
“More than anything, it was miscommunications and misunderstandings,” Lillard said. “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.”
Lillard always saw himself ending his career with the Blazers, even before he was dealt. The reunion came in unexpected fashion after Lillard suffered a torn Achilles during this past season’s playoffs. Milwaukee decided to waive him and use the stretch provision, allowing the Bucks to make a bold free agent signing, securing Myles Turner‘s services.
Collier reports that trading Lillard had been a consideration for Milwaukee if he did not suffer a long-term injury. The Bucks front office considered a number of different strategies with a Lillard trade being a last-ditch attempt to find another star to pair with Giannis Antetokounmpo.
Lillard chose to return to Portland on a three-year, $42MM contract after being waived. Cronin met Lillard at his Portland home to check on how he was doing, both mentally and physically with the rehab of his torn Achilles and spoke of the team’s progress during its rebuild. At that time, Lillard expressed that he felt the Blazers were on the upswing. An agreement was reached a short time later.
Lillard is expected to spend the entire 2025/26 season rehabbing the injury. Goodwin believes he’ll come back strong.
“It’s Dame. I know Dame,” he 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 was going to maybe even prolong his career because he goes so hard that he’s got to give his body a break.”
You would have thought he won multiple championships in Portland and was gone for a decade.
January 2024 was barley half a year after the trade. So basically he gave into the get out of Portland noise and instant regretted it
Ida preferred the money slot for mystery box X over this in all honesty for this org