When Damian Lillard expressed his desire to be traded from Portland in early July, one destination quickly emerged as his top choice: Miami. As reported by Chris Haynes of Bleacher Report, Lillard had a strong preference for the Heat, and Miami was eager to initiate talks with Portland to make a deal happen. Jimmy Butler even went as far as identifying Lillard as his top target for the offseason.
However, despite the mutual interest between Lillard and the Heat, progress on a potential trade was slow to materialize over the summer. Many believed that eventually, Lillard would find his way to Miami. After all, this is often how superstar trade requests unfold in the NBA.
Yet, in a surprising turn of events, the Milwaukee Bucks swooped in at the end of September and acquired Lillard in a three-team trade, sending multiple players and draft assets to the Trail Blazers. This unexpected move formed a new dynamic duo with Giannis Antetokounmpo, leaving Miami fans puzzled and asking one fundamental question: Why didn’t the Heat trade for Damian Lillard?
According to initial reports from Haynes, the Heat were prepared to offer a package centered around Tyler Herro, potentially including Duncan Robinson and draft picks. They were reluctant to include Caleb Martin in the negotiations. However, the Trail Blazers were reportedly unimpressed with this offer, as they already had promising young guards in their roster.
Beyond the offer itself, negotiations took a contentious turn. Lillard’s agent, Aaron Goodwin, conveyed to teams outside of Miami that acquiring Lillard meant acquiring an unhappy player. He made it clear to Barry Jackson of the Miami Herald that Lillard’s preference was to play in Miami, and this sparked a response from the NBA. The league issued a warning to Lillard and other star players, cautioning against implying that a player may not fully commit to their contractual obligations in the event of a trade.
As tensions rose, Portland’s general manager Joe Cronin ceased communication with Goodwin in mid-September. Additionally, there was resistance to the idea of Lillard participating in the team’s training camp. Lillard grew frustrated with the lack of progress in trade discussions and eventually came to the realization that the Trail Blazers were not keen on engaging with the Heat.
In Lillard’s words, “It was anything to go against what I would have wanted… Just based off how it was happening, I knew [it wouldn’t be Miami].”
With the Heat effectively out of the running, Lillard became open to the possibility of playing for the Bucks and the Nets. Goodwin communicated this interest to those teams, leading to increased pursuit from Milwaukee. The Bucks, operating discreetly, surprised the NBA world by finalizing a three-team trade with the Suns and Trail Blazers just before training camps began.
In the end, the Trail Blazers’ front office chose to accept Milwaukee’s offer, securing Damian Lillard in exchange for a package of players and draft assets. While some Miami fans may have been disappointed with how the situation unfolded, it’s hard to argue with the results, as Lillard found a new home in Milwaukee alongside Giannis Antetokounmpo.