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Chapter 8, Part 1: How Martin Got Schooled in Prison

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Chapter 8, Part 1: How Martin Got Schooled in Prison

This is Chapter 8, Part 1 of SMIRK. Was prison a “fun” walk in the park for Martin or a rude awakening? As usual, the truth lies somewhere in the middle.
Prison bars. (Illustration by Shannon Loys.)
Prison bars. (Illustration by Shannon Loys.)

So what was prison really like for Martin Shkreli? It’s a question a lot of people have asked. As a skinny, nerdy hedge fund manager-turned drug company founder, he seemed like he was in for a brutal culture shock, at the very least, when he lost his bail in September 2017. Speculation on the internet tended to run in the worst possible directions…like to prison rape jokes. Presumptively erudite media pundits also suggested all sorts of grim scenarios that were largely figments of their imagination.

“I dont think Martin Shkreli is going to make many friends in prison with his ‘I'm a smug jerk' routine,” one notable writer tweeted on the day Martin was remanded. (The same writer, whom I did formerly hold in high esteem, also seemed to suggest after the ELLE article about me was published in 2020 that all sorts of unspeakable harms and regrets would be visited on me just for telling the world I was Martin’s girlfriend.)

What did Martin say about prison when he came out? Being the type to minimize or deflect trauma, he was chatty and upbeat about the experience during his live streams on YouTube (which he resumed as soon as he was released) and in interviews with reporters he didn’t hate. (There were one or two of those besides me.)

He told one of those journalists, a reporter for the Daily Mail, that he had “too much fun” while in prison, including by finding ways to amuse himself and his fellow inmates, and teaching some of them about finance, economics and cryptocurrency. And he bragged about working with me, his then-girlfriend, to help two of the friends he made in prison win early releases. Both were serving lengthy sentences for drug crimes which seemed crushingly unfair.

But Martin had always had a habit of distorting things to the upside, including reflections of his own experiences. That was one of the ways he ended up committing securities fraud — by giving his investors a misleading impression that everything was fine when he had in fact lost their money and was devising an elaborate series of Hail Marys to make them whole. It was also important to him that his family, friends and internet fans see him as tough and unflappable. Thus that was the image he projected.

The only way to really know what was happening to Martin Shkreli in prison, and how he was handling it, was to have a front-row seat and watch the drama yourself — as well as gather perspectives from the inmates who got to know him. I had a front-row seat, or about as close to it as a person could have, during Martin’s prison years. And I developed relationships with many of the incarcerated men he became friends with. In all probability, I’m objectively the best source you’re going to find on what prison was like for Martin Shkreli.

From my viewpoint, prison was hardly a walk in the park for Martin. But most of the misery that happened to him wasn’t the result of interactions with other inmates. Being the sort of person who grew up in a working class home, and had no baseline pretensions, he got along well enough with plenty of men from disadvantaged backgrounds. Their struggles affected him deeply enough that he often went out of his way to help them, and risked disciplinary infractions for doing so. 

His suffering, which was ample, came mostly from the impossibly constricting and dehumanizing aspects of the bureaucracy; from public officials who undoubtedly made their careers partly based on punishing him as much as possible; and from corrections officers who either lacked basic compassion or just wanted to hassle him because he was the “Pharma Bro.” 

Barely a month after he was sent to the Metropolitan Detention Center, a high-security federal lockup in Brooklyn used as a jail, he called me in desperation because he wasn’t able to get his anxiety medication. I was still working for Bloomberg, sitting alone in a press room in a Wilmington, Delaware courthouse, where I’d been sent for the day to cover some sort of complex financial dispute.

It was the first time that I’d heard Martin’s voice since he was taken to prison. But when I answered the phone, which flashed “No Caller ID,” and went through the prison phone system prompts, he wasn’t in a mood for a casual chat. He was speaking rapidly in clipped and partially fleshed-out sentences. He said he didn’t get his Effexor, and he definitely needed his Effexor.

“It’s like ‘Oz’ in here!” he blurted out, referring to the HBO prison drama from the late 90s and early 2000s. 

The reason he didn’t have it was because…

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