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Now that Damian Lillard is a member of the Milwaukee Bucks, there will be plenty of retroactive analysis of the months that preceded it. Did the Blazers play their cards right? Could Lillard have done anything differently? For some, the big question is why Lillard, after making it known that he wanted to play for the Miami Heat, got traded somewhere else.

There are many ways to answer this question. One is to argue that Lillard, by signing an extension that will allow him to make upwards of $63 million in 2026-27 and then singling out Miami as his preferred destination, got in his own way. Another is to point the finger at the Heat for not being aggressive enough in their pursuit. The reality, though, is that it might not have mattered how Lillard or Miami handled the situation. If the Blazers didn't want what the Heat had to offer, there was no trade to be made.

"They just didn't want that stuff" is not nearly as interesting as a personal vendetta on Portland's part or some massive mistake by Miami. But just about everybody is saying it.

  • According to The Athletic's Sam Amick and Shams Charania: The two sides talked more than once in July; talks never went anywhere. The Blazers' initial ask was Jimmy Butler or Bam Adebayo, and, in July and August, the Heat were prepared to offer a deal that would have returned "up to three" first-round picks to Portland, along with Nikola Jovic, cap relief, pick swaps and second-round picks, with Tyler Herro ending up on a third team. The Blazers were "disinterested" in this, and, by the time Goodwin reached out to the Bucks and the Brooklyn Nets in mid-September, Lillard was "convinced" that it would be "virtually impossible" for Miami to acquire him.
  • From ESPN's Zach Lowe: "The two sides appear to have had no meaningful dialogue -- and maybe none at all -- since late July, per league sources. The Blazers had no major interest in any individual Miami player or draft asset, and limited interest in whatever combination Miami might cobble. The sides were far apart in initial talks, sources said."
  • The Miami Herald's Anthony Chiang reported that Portland "never expressed much interest in what the Heat was willing to offer" and that, after a conversation in July, "communication between the two sides was very limited" -- when the Bucks deal was coming together, the Blazers did not attempt to restart talks.
  • Yahoo Sports' Jake Fischer reported that, for most of the offseason, Portland and Miami "did not have significant conversations," and he described their negotiations in the past week as "nonexistent." 
  • On the "Lowe Post" podcast, Lowe said, "I think Portland maybe just didn't want what they had. One GM put it to me like this: Usually in a trade there's one asset a team really wants from you to make it work. The Heat did not appear to have that asset."

Milwaukee did not have, say, a 21-year-old Shai Gilgeous-Alexander to offer the Blazers. But it was able to give them a bunch of stuff they wanted. Portland now controls the Bucks' first-round picks in 2028, 2029 and 2030, and it would be reasonable to prefer this to having an assortment of picks and swaps from Miami, given that Milwaukee has an older roster and does not have the same history of luring stars in free agency. The Blazers also (for now) have Jrue Holiday on their roster, and they likely concluded that Tyler Herro wouldn't be valued as highly as Holiday as a trade piece. Agree!

And then there's the Deandre Ayton piece -- according to The Athletic, that part of the deal had been in the works since mid-July, and it was "an essential component to any Lillard trade" from Portland's point of view. It's possible that the Blazers could have worked this into a similar deal with the Heat (i.e. Caleb Martin, rather than the Bucks' Grayson Allen, could have gone to Phoenix), but's not a certainty -- Allen and the Suns have been linked for months, dating back to the ultimately anticlimactic Jae Crowder saga. Ayton has become an extremely divisive player for a former No. 1 overall pick signed to a max contract, but he's just 25 years old and fits this rebuilding Portland team a million times better than Nurkic did.

It is not clear that the Heat really did "everything they could to acquire Dame," as Goodwin said they did. ESPN reported that they "were reluctant to toss in every player and pick and swap the Blazers might have wanted in the end," i.e. all the picks, all the swaps, Herro, Jovic, Martin, Jaime Jaquez Jr., their choice of salary filler. This information, however, doesn't have to be seen as damning or even particularly consequential. Portland's front office knew all along what an all-in offer from Miami would look like, and it spent months trying to put together a more appealing option. When it found one, there was nothing for these two sides to talk about.