After 11 seasons with the team, arguably the greatest player in the history of the Portland Trail Blazers, Damian Lillard, has requested a trade and he has made it known it is his intention to play for the Miami Heat. None of this is surprising, it was not a surprise Lillard asked out and it is not a surprise he is angling to get to the Heat. The question becomes will Lillard get his wish and will the best offer Portland gets be from the Heat?
First, we need to break down what a deal to Miami may look like. If the Heat make the 2025 lottery protected pick they owe to the Thunder unprotected in 2026, Miami can offer 3 first round pick (2024, 2028, and 2030), 3 pick swaps (2025, 2027, and 2029), Tyler Herro, Caleb Martin, Jamie Jaquez Jr., Nikola Jovic, Haywood Highsmith, whatever 2nd round picks they have left, and salary filler. Since Jaquez just signed his rookie contract, he can’t be traded for 30 days after signing (not sure how many it’s been) so if Portland wants him, the deal cannot be official until for about a month but that does not really mean much. The Blazers also have too many guards on their roster, so they reportedly want to flip Herro and according to ESPN’s Adrian Wojnarowski, teams are willing to “surrender a good first round pick to the Blazers” to get Herro. Tyler Herro is good, after coming off of the bench for most of his career entering last season, winning sixth man of the year in 2022, he started all 67 games he played last season averaging 20.1 points, 5.4 rebounds, and 4.2 assists on shooting splits of .44/.38/.93. He did miss all but one game of Miami’s run to the finals so many are down on him but he can still play. The Nets are reportedly interested in trading for Herro. Would the Nets be willing to trade Dorian Finney-Smith, Royce O’Neale, and 2 first round picks? The picks would be the worst of the Suns, Rockets, and Nets picks in 2025 and 2027. If so, I have come up with a crazy 4 team trade. Damian Lillard, Jusuf Nurkic, and Royce O’Neale to the Heat, Tyler Herro and Haywood Higsmith to the Nets, Dorian Finney-Smith to the Hawks, and Kyle Lowry, Clint Capela, Caleb Martin, Jamie Jaquez, Nikola Jovic, 5 first round picks (Miami’s unprotected in 2024, 2028, and 2030 and the worst of the Nets, Suns, and Rockets in 2025 and 2027), 2 pick swaps from the Heat in 2027 and 2029, and 2 second round picks from the Heat in 2029 and 2030 (if the Heat still own those, I am not sure if they do) to the Trail Blazers.
It is a monster trade and one that lands Portland a lot of stuff. If they move Nurkic’s money, they’ll need a starting center, enter Clint Capela. Caleb Martin proved that he is good during Miami’s run to the Finals and can be either flipped or could be a key piece of Portland’s future. Jaquez and Jovic are interesting young players that could be a part of the Blazers future as well. They get 5 future picks and even though you would assume that 3 of them will be bad (the 2024 Miami pick and the 2 coming from Brooklyn), they are still guaranteed 5 first round picks, which should be seen as a huge win, not to mention the potential of those swaps with Miami. While there is not a player like Mikal Bridges or Shai Gilgous-Alexander in this trade, this is still a really good coup for Portland.
There are likely to be other offers for Lillard, with the Nets and Jazz probably having the best of the bunch. For the Nets they can put an offer of Finney-Smith, O’Neale, Spencer Dinwiddie, one (or both) of Dariq Whitehead and Noah Clowny (their first round picks this season), and first round picks in 2025, 2027, and 2029 from the Suns and a 2029 first from Dallas, all unprotected. Maybe they do a deal that includes Ben Simmons (I don’t see that as likely though). That is a good offer but probably a little too rich for Brooklyn’s blood because I don’t think that catapults them to the top of the Eastern Conference. Utah can offer Collin Sexton, Talen Horten-Tucker, Kelly Olynyk, Taylor Hendricks (the 9th pick in this past year's draft), and 3 or 4 picks from their treasure chest. I don’t think the Jazz will make an offer, it feels too soon to do this, no matter how good I think that team would be… but I think they’d be really, really good. A potential starting 5 of Lillard, Jordan Clarkson or Ochai Agbaji, Lauri Markkanen, John Collins, and Walker Kessler would be as good as any starting 5 in the Western Conference and they would probably be the best team, roster wise, Damian Lillard has played on. Their front court depth would be a concern but if Lillard was healthy and as dominant as he was last season, I really believe Utah could compete in what is a stacked Western Conference.
The Lillard for Jaylen Brown swap is one people love but I don’t see either side doing that because Brown can walk after the season and Boston would probably rather keep Brown than trade for Lillard. There is a Malcolm Brogdon, Robert Williams, Payton Pritchard, and all the picks and swaps trade Boston can offer, but that feels unlikely to me. The Harden and Lillard blockbuster exists, where the Sixers get Lillard, the Clippers get Harden (and Danuel House because every time I make this fake trade House ends up a Clipper), and the Blazers get Tyrese Maxey, the Clippers salary fillers, probably BJ Boston, and picks and swaps. However, with Brian Windhorst mentioning that the Sixers view Maxey as untouchable and the Blazers having too many guards already, this trade also feels unlikely.
With all this being said, I expect Lillard to end up in Miami. He has made it very clear that is what he wants to happen and though Trail Blazers General Manager Joe Cronin said they are going to take the best offer, I think what they can get in a Miami deal will be close enough for Cronin to accept it and grant Lillard his wish to play for the Heat. I would even go as far to say I would be shocked if Lillard was not playing for the Heat on opening night next season.
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