Fyre Fraud Offers a Depth of Insight into Billy McFarland, the Patron Saint of Millennial Con Men

The strangest part of the Fyre Festival media shitstorm, for me, was the fact that on the morning of the day it began to go viral, I had never heard the words “Fyre Festival” before.

I am a millennial, there’s no doubt about that. My birth date, in the late 1980s, puts me in the middle of that particular pie chart. But even as a millennial who writes about pop culture and entertainment, it could perhaps be said that I don’t conform to my generation’s “typical” relationship with the Internet and social media. Which is to say, I’ve never bothered to make a post on Instagram. I don’t know the names of any celebrity influencers. I wouldn’t be able to identify members of the Kardashian family, given photo evidence. None of those things are of any particular interest to me.

And that’s why the idea of Fyre Festival and its failure were initially so completely head-scratching. To hear that a bunch of people my age willingly forked over thousands of dollars to a con man, on the flimsiest of pitches, to travel to an island in the Bahamas and rub elbows with Instagram models? The rationale was alien to me. Who were these people? How were they so easily convinced to do something so stupid? And who was the guy behind it all?

Many of these questions receive (at least partial) answers in Hulu’s Fyre Fraud, a feature-length documentary that the streaming service surprise released on Monday, seemingly in an effort to preempt Netflix’s own Fyre: The Greatest Party That Never Happened, which arrives Friday. While casting some serious shade on its rival, Hulu’s documentary also achieves a coup: It boasts an exclusive interview with the festival’s creator and the story’s central figure, Billy McFarland. Netflix’s documentary can’t claim the same.

What can we learn from Fyre Fraud about McFarland, and how Fyre Festival went so desperately wrong?

Billy McFarland: Patron Saint of Millennial Con Men

A lot of movies have been made, over the years, about people who seem pathologically unable to live on the right side of the law. Sometimes, as in last year’s The Old Man & the Gun, it’s because they genuinely love their “work” in crime, such as it is. Even after being given multiple chances, they continue to commit the same crimes, fully accepting that it will almost certainly lead to another period of incarceration. The threat of jail time holds no particular menace for them, because they’ve already made their peace with that reality. They’ve weighed the pros and cons of their lifestyle, and found that they still prefer a world of robbing banks to one that involves working behind a desk, no matter the consequences.

Billy McFarland is not one of those guys. The difference between him and, say, Robert Redford’s character in The Old Man & the Gun is that McFarland was naively optimistic enough to somehow believe, in his heart of hearts, that he would never be caught and never be punished. He possesses a very special and very unusual suite of characteristics that are often negatively ascribed to millennials—entitlement, overconfidence, ambition, shamelessness, delusions of grandeur—but in McFarland’s case, they’re all cranked up to 11. Even when he was a child, McFarland displayed these same characteristics when he ran small-time cons in school. He looks back on those early stories and smiles, oblivious to the fact that he’s fondly remembering the same behaviors that would eventually earn him a six-year prison sentence. He doesn’t put two and two together.

Watching McFarland speak to the documentary team in Fyre Fraud reminded me of nothing so much as watching one of the serial killer interviews on Mindhunter. Somehow, he “takes responsibility” for the collapse of the festival, while simultaneously describing it as if “Billy McFarland” is someone other than himself. He lies compulsively, to the extent that he often appears to be conjuring entirely new lies on the spot. At one point, he tells the documentarians that there were actually “$2 million in houses” on the island, reserved for the festival—but that he lost a box containing all of the keys to those houses, which led to celebrity influencers spending the night in FEMA tents instead. When the documentarians say they have no evidence of the existence of those houses, McFarland sits there, staring off into space.

This is the same guy who began the conversation in a mood that was bubbly and positively cheerful, excitedly describing his plans for the festival and his childhood self, as if he somehow isn’t aware that the latter part of this interview will include questions about the multiple counts of fraud that have sent him to prison. Only when the interviewer actually gets to those questions do they become real for McFarland. The color leaves his face so quickly, you’d think he’d been cornered by Mike Wallace in a 60 Minutes ambush.

This “ignore all signs of trouble” mentality is ultimately the key to McFarland’s character. He was able to survive for years in the New York City market by never admitting defeat, by never falling on his sword. Every time he got in trouble, whether it was in the Fyre Festival planning or his previous credit card company Magnises, he got out of it in the same way—by robbing Peter to pay Paul. Every time an inescapable bill came due, McFarland simply managed to find another investor to foot it, while extending the deadline of his eventual unmasking. Every time the future of Fyre Festival seemed in doubt, McFarland found a way to wave away the problems and survive another day. His sheer disregard for the eventual consequences of his actions was ironically the thing that kept his duplicity from being discovered for so long, because anyone who looked at him couldn’t help but think “Nobody would be so brazen as to throw around money like this if they weren’t legitimate.”

And everyone was wrong. Billy McFarland was just that absurdly shameless.

Who Deserves Blame, and Who Deserves Pity?

Near the end of Fyre Fraud, the documentary goes out of its way to acknowledge the existence of Netflix’s Fyre: The Greatest Party That Never Happened, while dropping some relevant knowledge: One of the producers of Netflix’s documentary is Jerry Media, the advertising/social media agency that was hired to promote the Fyre Festival online, right up until the morning of the fest itself. Former Jerry Media employee Oren Aks, who also worked on promoting the Fyre Festival, speaks ill of his former company, criticizing their “we were only following orders ” defensive statement, which claims that “like the ticketholders, we were also misled.” When asked who is guilty, Aks replies “everyone,” including himself.

That makes for a compelling ending to a documentary, but I’m actually inclined to have a bit more sympathy for at least some of the people involved in McFarland’s orbit. The sheer number of employees working for him right up to the bitter end makes one wonder just how persuasive McFarland could be at the height of his powers. Numerous talking heads in Fyre Fraud tell similar stories of walking out of McFarland presentations, turning to each other and saying something like, “This festival is never going to happen.” But does it not damage the believability of those talking heads that every one one of them still agreed to be hired by McFarland to promote or organize some aspect of the festival? How obvious could the festival’s failure really have been in advance, if you agreed to attach your company’s name to it? Would you really choose to be the PR or social media organizer to something that would be an inevitable dumpster fire, even if it was going to pay well? It’s a little hard to believe.

EDIT: Producers of both documentaries have now obliquely accused each other of ethical gaps in their coverage. Fyre Fraud points out the conflict of interest inherent in having Jerry Media as producers, while the Fyre team disparages the fact that Hulu was willing to pay McFarland an unknown sum of money for its exclusive interview. Which documentary is taking the higher road in this scenario is still up for debate.

The originally advertised Fyre Festival “villa” tents.

One contingent that certainly deserves pity, and some redress of the damage that was done to them, are the Bahamian residents and workers of the festival, many of whom were ultimately never paid for their tireless efforts to build something that couldn’t reasonably be built. The night before the festival was supposed to begin, those poor contractors were still out there, building stages for acts that would never play, or even step on a plane, out of some misplaced sense of honor. You can’t exactly blame the Bahamian worker in Fyre Fraud who refers to McFarland simply as “a fuckshot,” whatever that means.

On the opposite end of the spectrum you have hip-hop superstar Ja Rule, whose depiction in Fyre Fraud is likely to be incredibly damaging. Originally brought in by McFarland as a co-conceiver and co-promoter of Fyre Festival, Ja Rule was named as a defendant in the $100 million class-action lawsuit stemming from the festival’s failure. As of October, Rule’s lawyers had filed a motion to dismiss the rapper from the case, claiming that he was simply a celebrity spokesman with no real knowledge of the festival’s operational problems. The footage in Fyre Fraud, however, shows Rule’s repeated visits to the festival site, and includes interviews with locals who claim to have literally told Rule that the festival was impossible. Set against video of a toast in which Rule salutes “living like movie stars, partying like rock stars, and fucking like porn stars,” it’s a scathing indictment of the rapper’s degree of personal responsibility. And, lest we forget, as Fyre Fraud points out, Rule’s own Iconn app lifted the idea of McFarland’s “Fyre” app and simply rebranded it with the same functionality—an app that lets you rent out celebrities for private functions, such as getting Cardi B to play your birthday party. Asked to clarify the fact that he’s still promoting a copy of McFarland’s app while trying to distance himself from the man legally, Rule says the following on video in Fyre Fraud: “It’s very different, but it’s similar.”

And then, of course, there’s McFarland himself. It’s almost tempting to pity him a few times during Fyre Fraud, in those brief moments when it becomes clear that his megalomania often bordered on some kind of mental illness outside his own control. Even while the festival was so clearly collapsing around him, and he was surrounded by unsolvable problems, McFarland’s mind often fixated on irrational side pursuits, such as the sudden compulsion that his team should find “a pirate ship” and bring it to the festival as a centerpiece. It’s those moments when you realize that although McFarland may have been a con man, he was hardly a standard con man. A competent con man would have collected the investments that poured into Fyre Fest and then disappeared to some kind of foreign haven with his ill-gotten gains, never to be seen again. It took a special kind of delusion to allow Fyre Festival to actually happen—to let the disaster unfold in real time, and only consider the ramifications afterward.

Ultimately, that’s what makes the story of Billy McFarland and Fyre Festival into such a compelling one. He’s a figure who represented all the worst aspects attributed to my generation, exaggerated to comic excess, and then was (finally) served a karmic comeuppance. It’s no wonder that the story trended as hard as it did, given that it so snugly fit the preconceptions that so many Internet users already have about the millennial generation.

Just know that we’re not all Billy McFarlands, when this is all said and done. Some of us don’t even use Instagram. Honest.

Jim Vorel is a Paste staff writer. You can follow him on Twitter.