The Metropolitan Detention Center stood like a grim fortress near the waterfront in Brooklyn’s Sunset Park. The 10-story cube of brick and stone loomed over neighboring warehouses, administrative buildings and a waste-processing center. Built like a safe, it kept its occupants cut off from society and, for the most part, from sunlight. Its windows were six-inch-wide slits. 

On a late afternoon in November 2017, I made my way to this unwelcoming structure. I reached my hand compulsively up to knead the muscles tightening over my sternum, a sign of my panic disorder flaring. This would be my first visit to a prison. I wasn’t sure what to expect.

By now, if you’ve been reading SMIRK, you know who I was there to see: Martin Shkreli, the infamous “Pharma Bro,” who jacked up the price of a toxoplasmosis drug enormously, became the internet’s most hated villain, got convicted of securities fraud and was thrown in federal prison, all within 24 months.

He was also a slim, delicate-looking nerd, and much more emotionally vulnerable in person than any of his online jackassery would suggest. I had come to know that side of him gradually over years of interacting with him first as a journalist and then as a friend. I struggled to imagine him, or any other human being, eating, sleeping and surviving day after day in that sh*thole.

In my work as a legal journalist, I had spoken with enough people convicted of white collar crimes to be familiar with jailhouse stories. But those experiences usually involved stays at minimum-security prison camps, by far the least miserable accommodations the federal Bureau of Prisons can offer.

Those were the places journalists scoffingly labeled “club feds,” mainly because they were relatively safe and somewhat less dehumanizing than higher security facilities. They lacked razor wire fences, for instance, and strip searches were less routine. Sometimes they also had more recreation options…