In the annals of Heat Culture, Wednesday's reported trade of Damian Lillard to Milwaukee for Jrue Holiday and draft picks in a three-way deal with Phoenix will go down as both a dark and a deeply informative day.
The NBA's best organization from top to bottom took a massive L as the trade it had clearly been working toward for three months was never really even seriously negotiated, and its Eastern Conference rival will get to enjoy Dame Time instead.
The Heat had been linked to Lillard since before he had even demanded a trade. There were rumors going back to midseason that if Lillard's previously undying loyalty were to meet its demise, Miami would pounce.
As soon as Lillard's representation gave word he was requesting a trade, it came with the edict: Miami, only Miami, and nowhere else.
Typically when a player of Lillard's stature leaves a team, his wishes are respected and a deal is worked out. There was just one problem: the Heat were uniquely positioned to not have assets to trade in such a deal.
Usually, such deals involve high-value draft assets acquired from other teams, young prospects, or ideally, both, combined with expiring contracts.
Miami had none of that as the Heat consistently short change the future in order to win now — a perpetual demand from Pat Riley. The joke around league circles being that Riley is surprised every June to even discover the draft exists.
Tyler Herro is just 23 and played a key role in the 2020 NBA Finals, but he begins a four-year, $120 million extension this season, and there's at least been a debate that the Heat's 2023 Finals run was in part due to Herro's injury absence. That's not fair to Herro, but it did bring down the value in the one blue chip Miami had.
Other than that, the cupboard was bare.
Miami tried to engage other teams in talks for another first to add for Herro. The problem, however, was Miami never really got to negotiate.
Lillard's representation knew the Heat's offer was never going to be great and an open market would almost certainly bring in superior offers for one of the league's best offensive players.
So, they poisoned the well.
Reports poured in that Lillard only wanted Miami and would refuse to play for another team. However, no one believed that.
Lillard's reputation in the league is stellar.
"He's a leader," one executive not involved in talks said this summer. "It would be against everything in his character history if he were to refuse to play. It's not how he's wired. He shows up and does the work."
But the risk was still there and it deterred a full market from developing.
So, Portland shut down talks until closer to media day and ultimately elected not to include the Heat. Miami's best offer wasn't something the Blazers wanted, so they simply didn't engage.
Sources suggested that Miami never received a call to discuss terms this week and didn't get a chance to counter the Bucks' offer.
Ultimately, there is only so far a franchise can be pushed before it reacts and protects itself. Over the past week, Portland sought to create a market for Lillard and negotiated with teams like Toronto, Philadelphia, Chicago … and Milwaukee.
Andscape reported the following on Wednesday evening:
Sources to @andscape: With Miami talks going nowhere, agent Aaron Goodwin privately told the Bucks and Nets 10 days ago that Dame would be interested in a deal there. The Raptors were a real contender to land the ex-Blazers star, but ultimately Bucks got it done per Woj report.
— Marc J. Spears (@MarcJSpears) September 27, 2023
Miami's best chance at landing Lillard fell with its uncompromising approach of "win now, figure everything else out later."
The media blitz also put Portland on the defensive. Limiting lifelines is one thing, pushing them to desperation is another. Heat media outlets reported various things Miami wouldn't include in the deal. Some reports said the Heat hoped to keep Herro, others that Caleb Martin wouldn't be included. There were also reports that said only one of the young players — either Nikola Jovic or Jaime Jaquez — would be in the deal.
A team with a bad package to start was projecting it wasn't going to give everything for a player it had essentially built its offseason around.
The Heat didn't collaborate on Lillard's camp's efforts to close off suitors. They just suffered the consequences as Portland elected to not give them the chance to make the offer they likely should have made initially.
Miami has now struck out on potential superstar trades for Kevin Durant, Giannis Antetokounmpo and Lillard.
The Heat will be fine. They still have one of the best players in the league in Jimmy Butler, one of the best versatile big men and a top-five defender in Bam Adebayo, and the best coach in the NBA. They have found diamonds in the undrafted-free-agent rough, and their front office — headed by Andy Elisburg and Adam Simon — is one of the best in the league.
But after losing two rotation players this summer in Gabe Vincent and Max Strus, the hill is steeper than it was to end the season, and far steeper than they thought it would be.
Lillard was supposed to be the third star, the final piece to get Miami over the championship hump and heading downhill in the title race for the first time since 2013.
Instead, Miami finds itself, once again, running up that hill.
