SMIRK (audio version)
Chapter 16, Part 2: The Age of Man-Boys

Chapter 16, Part 2: The Age of Man-Boys

Masculinity is having a moment. It’s a toxic, deranged, self-sabotaging moment – but it may be the right one for Martin Shkreli.

Eight years after he hiked the price of Daraprim and was christened the “Pharma Bro,” the world finally got ridiculous enough to accept, and maybe also forgive, Martin Shkreli. 

There was no redemption narrative. Still shockingly impervious to hitting “rock bottom,” he snapped back into all his old habits after prison – including spinning elaborate fantasies, falling short of his promises, and endlessly collecting Discord groupies. He didn’t atone for past mistakes or demonstrate any meaningful signs of emotional growth. Martin was still Martin.

What had changed was the context around him. During his time in prison and in the year after his release, a wave of narcissistic, immature, unruly, authority-snubbing man-children catapulted to ever-more spectacular heights and exploded into ever-larger supernovas of infamy.

“Crypto bros,” who arose from a multi-trillion-dollar asset class fueled almost entirely by sophomoric humor and pandemic boredom, eclipsed Martin’s frauds. Day traders who congregated on the subreddit WallStreetBets and looked to Martin as an inspiration accomplished incredible feats of meme-based market coordination that he could only dimly fathom.

And then there was the Final Boss of the man-boy movement, the world’s wealthiest human Elon Musk, who LOL’ed his way into a financially nonsensical $44 billion takeover of Twitter.

Illustration of Elon Musk, Martin Shkreli, and Sam Bankman-Fried.
Illustration of Elon Musk, Martin Shkreli, and Sam Bankman-Fried.

Stacked against their absurdities, Martin looked, well, kind of normal. On some dimensions, he even came out ahead. Slowly but surely, members of the press started to notice the differences and make roughly favorable comparisons. 

Take the situation with disgraced crypto wunderkind Sam Bankman-Fried. Criminally charged with running his massive FTX crypto exchange as a Ponzi scheme, Bankman-Fried lost his bail for witness tampering; he had leaked substantial amounts of private materials from his ex-girlfriend, widely expected to be a key government cooperator against him, to the New York Times. 

Just like in 2017 when Martin lost bail for posting a $5,000 “bounty” on Hillary Clinton’s hair, Bankman-Fried was taken to the dungeon-like Metropolitan Detention Center in Brooklyn. Unlike Martin, who suffered bad food, dismal surroundings, and spotty access to his anxiety meds with relatively little complaint (apart from the time he called me while having a panic attack), Bankman-Fried behaved exactly like a caricature of a spoiled rich kid.

Because the prison was unable to accommodate his vegan diet, he subsisted on nothing but bread, water, and peanut butter, his lawyer lamented to a judge. Bankman-Fried was also unable to obtain his prescribed Adderall, a common medication for ADHD, the lawyer said.

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Needless to say, the lawyer didn’t win many sympathy points for Sam. Far too many prison inmates have suffered far worse deprivations than a lack of vegan meal options or ADHD medication. For instance, inmates at the MDC (including Martin) have had to endure frozen temperatures in winter without a working heating system. The situation got so bad by 2019 that it sparked protests.

I marveled at how Bankman-Fried had grown up as a child of two Stanford University law professors and remained so naive about the harsh realities of the justice system. Martin — whose parents were immigrant janitors, not law professors — also had a strong reaction. He gloated at Bankman-Fried’s tributions and savored a taste of schadenfreude.

He opined gleefully to anyone who would listen about what other miseries he expected SBF to experience. The MDC was a “very testosterone-filled, masculine place” he told a crypto journalist during a podcast. He advised that voluminous-haired Bankman-Fried should shave his head, deepen his voice, and learn about “criminal culture.” 

“He should be listening to as much rap music as possible… pick those things up as quickly as he can,” Martin said. “Learn everything there is to know about gangs, about the tough neighborhoods in every city.”

Mainstream journalists reported on Martin’s observations in wry amusement but did not flame his comments as implausible. Martin, after all, had done the time and deserved at least that much respect. He wasn’t just flapping his gums.

Months earlier, he also got a cheeky nod from John Oliver on HBO’s “Last Week Tonight.” During a segment on the crypto market’s collapse, Oliver showed a clip of Martin crashing an online group video chat with Do Kwon, the founder of a supposed “stablecoin” called Terra that suddenly lost nearly all of its value, wiping out investors. Kwon, a South Korean, was on the run from various legal authorities. 

As soon as his presence was noticed, Martin cheerfully and semi-randomly announced to Kwon: “Jail’s not that bad.” Kwon and the other participants giggled uncontrollably. 

“I don’t think there’s ever been a more cursed Zoom call,” Oliver quipped. It was the kind of good-natured ribbing Martin easily could have laughed along with.

The media tiptoed further toward Martin’s corner after he launched a campaign of pestering Elon Musk for not restoring Martin’s original Twitter account. Martin lost it in January 2017 for harassing writer Lauren Duca by ostentatiously pretending to be madly in love with her. 

Musk claimed he would be a champion of freedom of speech on Twitter, which he confoundingly renamed “X.” He welcomed back numerous accounts that were banned for hate speech and other bad behavior, including former president Donald Trump’s. But he did not, as many people (including me) anticipated, allow Martin to return. Instead, a pre-Musk policy continued of looking the other way as Martin used alt accounts, only to pull the plug as soon as he was able to attract significant media attention.

I found it strange that literal white supremacists and Nazis had been allowed back on Twitter, but Martin remained banished. You could even call the decision hypocritical. Musk had gotten into plenty of weird, off-putting tiffs himself on the site. For instance, there was that time he called a hero diver who saved children trapped in a cave a “pedophile.” Martin’s over-the-top facetious flirting couldn’t possibly be worse.

Maybe Musk was busy concentrating on curbing a mutiny from high-profile journalists, celebrities and other influential users who regularly complained about the reappearance of the formerly ostracized hate-speakers and threatened to leave “X.” Maybe Musk saw Martin as the proverbial straw that would break the camel’s back, sending users into full-blown exodus. Or maybe he just didn’t care about the “Pharma Bro.” 

Whatever Musk’s reasons were, the moment was primed for Martin to throw down the gauntlet in the best way he knew how. He publicly offered $10,000 (later upping the offer to $15,000)  to anyone who could help him get his account back. It was the right ridiculous thing to do at the right ridiculous time.

Whether he realized it or not, Martin stepped directly into a prewarmed media frame. Just weeks earlier, Musk had jokingly challenged Facebook CEO Mark Zuckerberg to a “cage match,” and “Zuck” – a trained jiu-jitsu competitor – happily accepted. Speculation abounded about whether the two geeky social media billionaires would fight hand-to-hand in a sort of dystopian late-stage capitalist duel (so far, they have not).

“Forget Zuckerberg. It’s Elon Musk vs. Martin Shkreli in a battle over his X account,” Fox Business host Charlie Gasparino reported. Although the fight was not physical, the implication was embedded in the story. The circumstances provided Martin with an opportunity to explain, in an interview with Gasparino, that “Elon preaches free speech, but his actions are showing the opposite.” 

The story got more play because it also involved Musk’s occasional baby momma, Canadian musician Grimes. Martin had interacted on Twitter with her, in an attempt to lobby for his original account to be restored. She tweeted that she would “fight” for his handle if he agreed to “more ethical behaviors.” Unsurprisingly, Martin didn’t take the bait.

I sensed that Martin could probably reenter mainstream society fairly quickly, along with “X,” by just doing some sort of big “mea culpa.” I took Grimes’ comments as a suggestion that people might be ready to hear and accept an apology from Martin. He wouldn’t make that move, though. Martin’s pride, just like the rest of him, was too buoyant. The realization saddened me.

Still, I was impressed he had gotten the right conversation started. I sent him a DM telling him so. “You might actually get your account back!”I wrote.

“Why do you say that, I probably won’t,” he replied.

After everything, he still didn’t think I could possibly be right.

SMIRK (audio version)
My experiences uncovering the story of, and falling in love with, Martin Shkreli.