Bill Simmons took the Miami Heat to task on his podcast, "The Bill Simmons Podcast," for failing to land Damian Lillard during the 2023 offseason. He didn’t hold back in calling out the franchise and its media ecosystem for botching what seemed like a foregone conclusion: that Lillard would be heading to Miami to team up with Jimmy Butler and Bam Adebayo.
"Herro, Jovic, Duncan Robinson, two Miami firsts, and one Miami swap. And instead, they did Ayton, Jrue Holiday, a Milwaukee 2029 first, and two Milwaukee swaps. So I'm gonna make the case they actually still did the right thing."
"I just don't think they got enough for Jrue. I think, so here's the thing. I was just telling somebody this the other day. Miami, and their whole little annoying media machine that they have, f**ked up that Portland situation to that point that Joe Cronin & the Portland people were like “we’re never trading with those f**king guys."
"And they end up making the damn trade. They get Jrue back and now they're like, Jrue's like, I wanna be in a contender like, we got you, we're gonna trade you a contender. And they still won't trade him to Miami, the team that probably needed him the most, right?"
"And all the s**t Miami did that summer led to them not getting Jrue Holiday who also would have blocked Boston from getting Jrue Holiday. They said they had to settle for Rozier in February."
"They did 90 different ways about how f**king stupid Portland was for not taking their hero deal. And we were calling it out on the podcast. All these different media people that, let's be honest, are a little Miami Heat friendly, and they were super aggressive about it."
"I think Portland got pissed off, because the fact that they didn't trade Jrue to Miami tells me they were pissed off. Plus, I've heard they were pissed off."
Bill Simmons broke down the failed negotiations in his characteristic candid style. He contrasted Miami’s offer with the package that Portland eventually accepted from Milwaukee. While acknowledging that Portland might have gotten less for Jrue Holiday than expected, Simmons suggested that Miami’s media machine played a pivotal role in ruining their chances of landing Lillard.
Simmons pointed out that the Heat's overly aggressive stance in the media likely turned Portland off from dealing with them altogether. The host speculated that the situation was so soured that the Blazers wouldn’t even entertain trading Jrue Holiday, who was also part of the Lillard trade, to Miami.
It’s a scathing critique, but one that offers insight into the often unseen machinations behind high-stakes NBA trades. According to Simmons, the Heat’s inability to handle the negotiations with Portland properly not only cost them Lillard but also an opportunity to acquire Jrue Holiday, who ultimately ended up in Boston.
Simmons also suggested that the Heat's constant media pressure and public comments about how they deserved Lillard may have ultimately backfired. He implied that this frustration resulted in the Blazers intentionally avoiding any trade with the Heat, including for Holiday, as a form of retribution.
Simmons’ take isn’t just speculation; it underscores a broader issue within the NBA, where media narratives and public posturing can sometimes affect negotiations. The Miami Heat were coming off a Finals appearance in 2023, and Damian Lillard had openly stated his desire to join the franchise. All signs pointed to Miami as Lillard’s next destination, especially considering their track record of building championship contenders around star players like Jimmy Butler and Bam Adebayo .
In the end, Lillard ended up in Milwaukee in a shocking twist, teaming up with Giannis Antetokounmpo instead of Butler and Adebayo. The Heat were left empty-handed, and many fans and analysts were left wondering how the situation fell apart. Simmons pointed to Miami's aggressive approach, implying that it rubbed Portland's front office the wrong way, leading them to seek alternative trade partners.
One of the critical moments came when the NBA issued a memo regarding Lillard’s trade request, which mentioned reports that Lillard’s agent had told teams not to bother trading for him because he only wanted to go to Miami. The memo essentially served as a warning that the league would not tolerate a one-team trade demand, and it likely contributed to the Heat’s inability to close the deal.
The failed pursuit of Lillard was compounded when Jrue Holiday, who was part of the Lillard trade to Milwaukee, became available for a trade. The Heat, again, seemed like a natural fit for Holiday’s services, particularly after missing out on Lillard.
Yet, Portland traded Holiday to the Boston Celtics, a team that was already loaded with talent. This move significantly strengthened one of Miami’s biggest rivals in the Eastern Conference while leaving the Heat without the reinforcements they needed. The Heat faltered in the first round and the Celtics won a record 18th NBA title.
From Simmons' perspective, the Heat’s mismanagement of the entire situation had significant consequences. Not only did they miss out on Lillard, but their approach may have alienated Portland to the point where they wouldn’t consider Miami as a trade partner for Holiday either. Instead of building a roster that could contend for a title, Miami now faces a future where they must regroup after missing out on two premier talents.
The Miami Heat’s failed pursuit of Damian Lillard was one of the most surprising and talked-about stories of the 2023 offseason. What seemed like a sure thing fell apart, and Bill Simmons believes the Heat's own aggressive tactics were partially to blame. By pushing too hard, both publicly and privately, Miami may have alienated Portland's front office, costing them not only Lillard but also Jrue Holiday.
Now, the Heat must reckon with the fallout and figure out how to remain competitive in a suddenly much stronger Eastern Conference.
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