Damian Lillard
The most excruciatingly painful trade rumor as a Heat fan came with Damian Lillard just one summer ago. The Heat were coming off yet another Finals run at the time and were at their best (and possibly last) position to acquire that missing piece to finally win it all. Lillard formally requested a trade from the Portland Trail Blazers and specifically had Miami as his only preferred trade destination.
Breaking: Trail Blazers star Damian Lillard has requested a trade out of Portland, sources tell @TheAthletic @Stadium. The Miami Heat and Brooklyn Nets are among leading suitors for one of the NBA’s 75 Greatest Players ever. pic.twitter.com/nw8OIepAHz
— Shams Charania (@ShamsCharania) July 1, 2023
A potential pairing between the two parties would’ve provided Miami with a bonafide star backcourt scorer to a team that lacked point guard depth. There was also a public close relationship both on and off the court Lillard and Adebayo over the years.
The fact that no other teams were even on Lillard’s radar made it almost certain that the Heat were finally going to get a blockbuster deal done. In what was their last realistic chance at capitalizing on Butler’s window, the Heat and Lillard fumbled the opportunity.
Trade talks never happened in good faith as Cronin was reportedly disinclined to grant Lillard his wish. Instead, Cronin traded him to the Milwaukee Bucks in a three-team deal involving the Suns. The Heat were left empty-handed.