When Damian Lillard requested a trade out of Portland in early July, one destination immediately shot up to the top of the seven-time All-Star's list: Miami.
As Bleacher Report's Chris Haynes revealed at the time, the Heat were Lillard's preferred team, and Miami was motivated to "quickly engage with Portland" and try to complete a deal. Jimmy Butler even reportedly told the organization that Lillard was his "No. 1 target" during the offseason.
And then, well, nothing. Despite Lillard and the Heat both pushing for the Trail Blazers to finalize a trade, there was hardly any progress made throughout the summer. Still, Lillard would eventually land in Miami, right? That's just how superstar requests work in the NBA.
Nope. The Bucks crashed the party in late September, acquiring Lillard in a three-team deal that sent multiple players and draft assets to the Trail Blazers. Milwaukee formed a new dynamic duo of Lillard and Giannis Antetokounmpo, and Miami fans were left asking one simple question...
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Why didn't the Heat trade for Damian Lillard?
Haynes initially reported that the Heat were "prepared to offer a package centered around Tyler Herro, with possibly Duncan Robinson and picks." They wanted to avoid including Caleb Martin in trade discussions, per Haynes.
The Trail Blazers were "not impressed" with the Heat's offer, according to ESPN's Adrian Wojnarowski. They already had young guards in Scoot Henderson, Shaedon Sharpe and Anfernee Simons, so they didn't consider Herro a great centerpiece in a blockbuster deal.
In addition to the issues with the offer itself, trade negotiations also turned ugly. Lillard's agent, Aaron Goodwin, told franchises outside of Miami that "trading for Lillard is trading for an unhappy player," per Wojnarowski. He told the Miami Herald's Barry Jackson that Lillard "wants to play in Miami. Period."
Goodwin's tactics prompted the NBA to send a warning to Lillard and other star players considering future trade requests. The league declared that it could hand out harsh penalties if a player or agent suggested that the player will "not fully perform the services called for under his player contract in the event of a trade."
Portland general manager Joe Cronin stopped communicating with Goodwin in mid-September, according to The Athletic's Sam Amick, and he pushed back on the possibility of Lillard participating in the team's training camp. Lillard grew frustrated with the lack of movement on a deal, eventually realizing that the Trail Blazers weren't interested in engaging with the Heat.
"It was anything to go against what I would have wanted," Lillard told Amick. "That part was irritating. Just based off how it was happening, I knew [it wouldn't be Miami].
"[The Trail Blazers] hadn't talked to Miami. So once it started happening like that, then I started hearing about all these other random teams, I was like, 'I'm probably not going to Miami.' So I wasn't holding on to that too [much]."
How Bucks beat Heat's offer for Damian Lillard
When the Heat were essentially eliminated from the Lillard sweepstakes, the 33-year-old guard "became open to the prospect of playing for the Bucks and the Nets," per The Athletic's Shams Charania and Amick. Goodwin reportedly shared Lillard's interest to those teams, and Milwaukee's pursuit intensified.
The Bucks moved in silence, stunning the NBA world when they completed a three-team trade with the Suns and Trail Blazers before the start of training camps. Portland never re-engaged with Miami before accepting Milwaukee's offer, according to the Miami Herald's Anthony Chiang.
Here is the full breakdown...
Bucks receive:
- Damian Lillard
Suns receive:
- Grayson Allen
- Keon Johnson
- Nassir Little
- Jusuf Nurkic
Trail Blazers receive:
- Deandre Ayton
- Toumani Camara
- Jrue Holiday
- 2029 unprotected first-round pick
- 2028 unprotected swap rights
- 2030 unprotected swap rights
The Trail Blazers were then able to flip Holiday to the Celtics in exchange for Malcolm Brogdon, Robert Williams III and two future first-round picks. Portland could also move Brogdon in the future for more assets depending on how the season plays out.
While the Heat faithful didn't appreciate how the Trail Blazers' front office operated, it's difficult to argue with the final results.
