America's Most Hated CEO Just Got Sentenced to Prison. Here's What It Will Be Like For Him

His cockiness was gone. Minutes before he was sentenced to prison, the man known as the “Pharma Bro” and the “most-hated CEO in America” broke down in tears, to the point that the judge asked a clerk to hand him a box of tissues.

Barring an appellate miracle, Martin Shkreli, just a few days shy of his 35th birthday, will be in his 40s before he walks the street a free man again. Judge Kiyo Matsumoto  sentenced him Friday to seven years for his stock fraud conspiracy convictions.

It wasn’t quite as harsh a sentence as prosecutors wanted; they’d asked for 15 years, but it was much more severe than the 18 months Shkreli’s lawyers asked for. It’s certainly much more than the “time served” at “Club Fed” Shkreli had predicted he’d get, and where he thought he’d be playing tennis and XBox.

There’s little sympathy for Shkreli on the outside–except for a small but passionate group of supporters, many of whom followed him on social media, and think he got royally screwed over.

Even during his trial, Shkreli seemed to try to show he wasn’t taking seriously: dropping in on reporters (he called the prosecutors “junior varsity”), using social media during the evenings, refusing to wear a tie, and simply reading a book during closing arguments.

Still, it’s not the stock fraud and conspiracy that he’s known for; it’s the notoriety he received as a drug company CEO, when he hiked the cost of an antiviral drug by 5,455 percent (from $13.50 to $750 a tablet)–and seemed to revel in the bad publicity.

What will life be like now for Shkreli, in prison? It’s impossible to predict, but the Internet is awash with accounts of what life is like behind bars for white collar federal prisoners like Shkreli.

In a word, it would seem, Shkreli’s time will likely be “difficult,” for three main reasons:

  1. Because the cushy Club Fed-style prisons he seemed to anticipate doesn’t really exist anymore (if they ever really did).
  2. Because Shkreli is already well-known, and likely still fairly wealthy, even after he’ll have to forfeit more than $7 million and pay a $75,000 fine.
  3. Because if there’s one thing Shkreli has proven, it’s that he has a really difficult time controlling his ego and his mouth. That causes people to feel passionately about him on the outside, and it’s hard to imagine him changing quickly behind bars.

There’s one consolation for Shkreli: The judge sentenced him to less than 10 years, so he’s far more likely to do his time in a minimum security federal prison camp, than a tougher, higher security facility.

Depending on where he winds up, the prison camp he’s at might not have razor wire or even many locked doors. The threat of more time in a tougher facility is enough to keep most people from walking away.

But it’s not fun, and as several well-known people who spent time in federal custody have explained, the deck is stacked against people with a public profile.

“The more ‘high profile’ you are–unlike in the non-prison world–the fewer perks you may receive,” according to a Business Insider article a few years ago profiling former NYC police commissioner Bernie Kerik, who spent four years in federal prison for tax fraud, among other charges.  

“Once you arrive at prison–I was shocked by the psychological punishment,” said Kerick who was in the kind of federal prison camp where Shkreli is likely to wind up. You are constantly berated, degraded, demoralized,” he says. “You’re herded like cattle.”

Another former federal white collar prisoner, Mike Kimelman, who was convicted of insider trading and spent 15 months in prison, had a harsh description for it as well.

“I learned what an abject disgrace our prison system is (really the entire criminal-justice system),” he told Turney Duff at CNBC. “While I get that it’s supposed to be punitive, I find it hard to believe that the American public would allow it to exist in its present state if they knew what it was like.”

And, Matthew Kluger, an attorney who got 12 years for insider trading, and gave an interview while still in prison.

“The couple things that are the worst about being here, have nothing to do with the facilities or things that you can show visually on TV. … Here, you look around, and it looks pretty nice,” he said. “[I]f this were filled with 1100 people that you want to hang out with, this would be a fine place to be. Unfortunately it’s not.”

The biggest challenge, he added, “is other people. It’s being with this diverse crowd of people who are generally angry, somewhat antisocial, not the kinds of people that you want to spend your time with in the outside world. So that makes it hard.”

(Kluger’s interview by the way, is really long and wide-ranging on life in a federal prison; if you’re really interested in this it’s worth checking out. He’s still inside, too, until 2022.)

There is certainly life after 40, and Shkreli’s last act has yet to be written. But leave no doubt: this is a harsh sentence and he faces years of difficult challenges as a result.