More than a few folks out there will argue that the Milwaukee Bucks won the offseason with their blockbuster acquisition of Damian Lillard. This is especially after the Bucks pretty much hijacked this deal at the last minute from the Miami Heat.
Lillard himself stated that Miami was his preferred trade destination but in the end, his wish just never came to fruition.
Damian Lillard’s Agent Played Key Role in Botched Heat Deal

As it turns out, Lillard’s sports agent, Aaron Goodwin, may have played a pivotal role in his client’s failed move to South Beach. While Goodwin may have been trying to do whatever he could to facilitate Lillard’s trade to the Heat, it appears that he may have actually sabotaged the deal unintentionally.
According to NBA insider Ben Maller of Fox Sports, the actions of Lillard’s agents were one of the reasons why the Blazers decided to pull the plug on the Heat deal:
“From what I’ve gathered, Portland was prepared to send Lillard to Miami,” said Maller (h/t Nico Martinez of Fadeaway World. “Then his agent gave some comments to the media that rubbed several people in Portland the wrong way. It was at that point that the Blazers pivoted. Lillard’s agent had embarrassed the franchise.”
"From what I've gathered, Portland was prepared to send Damian Lillard to Miami, and then his agent gave comments to the media that rubbed people the wrong way in Portland, so they pivoted."
🎙️@benmaller on Dame claiming Blazers did him dirty pic.twitter.com/ELkHXh1Tx4
— FOX Sports Radio (@FoxSportsRadio) October 12, 2023

Goodwin may have been acting in his client’s best interest but in the end, his words and his actions backfired on Dame significantly.
It All Worked Out for Milwaukee Bucks

One thing you can say for sure is that Bucks fans aren’t complaining about these developments at all. Miami’s inability to close the deal — which apparently, also had a lot to do with Portland’s unwillingness to find common ground — led to Milwaukee landing the seven-time All-Star.
Obviously, the Heat’s offer did not meet Portland’s valuation for their now-former cornerstone superstar. The Bucks capitalized on this by putting an offer on the table that the Blazers could not and did not refuse.
All is well that ends well. Except for the Miami Heat, that is.
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