Damian Lillard’s recent move to the Portland Trail Blazers was one of the biggest shocks of the 2025 NBA free agency period. After the former Bucks star was waived by Milwaukee, many predicted he would land at a contender; however, he ultimately ended up flipping the switch and returning home.
However, on a recent episode of his podcast, Aaron Fentress of The Oregonian offered further details about how Lillard ended up in Milwaukee, including a potential link to the Miami Heat that never came to fruition.
NBA Insider Reveals Heat Were Damian Lillard’s Preferred Destination
On a recent episode of his podcast, Fentress shared a shocking detail about Lillard’s decision to sign with the Bucks in 2023, revealing that the star point guard never wanted to play there in the first place.
“He didn’t want to go there in the first place; he wanted to go to Miami. He relented and went to Milwaukee because his agent talked him into it, right? It gave him a chance to win.” During the episode, the insider explained Lillard’s potential link to the Heat.
When Lillard requested a trade from the Trail Blazers in 2023, the Heat were his No. 1 preferred landing spot. However, Portland and Miami couldn’t agree to a deal, and Lillard was traded to the Bucks, where he spent two seasons.
According to reports, Aaron Goodwin, who was Lillard’s agent when he decided to leave Portland in 2023, relayed to teams that Lillard would not be content if Portland traded him to a team other than Miami; however, the move never came to fruition.
“Some teams I did call. Other teams have called me. It’s a respectful relationship with most teams. Truthfully, he wants to play in Miami. Period.” Lillard’s agent explained back in 2023. Nevertheless, Portland was adamant on getting the best possible deal it could.
Shams reports Aaron Goodwin denied telling teams not to trade for Dame.
Aaron Goodwin on the record to the Miami Herald on July 6: “Some teams I did call. Other teams have called me. It’s a respectful relationship with most teams. Truthfully, he wants to play in Miami. Period.”
— Sean Highkin (@highkin) July 28, 2023
Ultimately, the one-time Rookie of the Year was moved to Milwaukee in a three-team blockbuster that sent Jrue Holiday and Toumani Camara to Portland.
Despite earning All-Star nods in each of his two years with the team while averaging 24.6 points and 7.0 assists per game, Milwaukee was knocked out of the playoffs both years, with Lillard suffering a torn Achilles in Game 4 of the Bucks’ first-round series against the Pacers in April.
On July 7, the Bucks officially waived Lillard. They stretched the remaining $103 million left on his contract to help facilitate the signing of free agent center Myles Turner to a four-year, $107 million deal, ending the 2x Bucks All-Star’s time in Milwaukee.
“He wasn’t necessarily happy; there wasn’t anything against Milwaukee or the Bucks or anything like that where he didn’t necessarily want to be there, but he did want to win,” he added. “But the fit never really worked out,” Fentress explained further.
While Lillard ultimately had great individual success with the Bucks, the franchise never made it click in terms of contending for a championship, leaving fans to question what might have happened if Dame joined Miami back in 2023.