When I was four, my grandmother’s mailman was named Todd Postman. I thought that was fucking hilarious. Less hilarious, but equally “funny,” was a vicious serial rapist I encountered whose last name was Conquest. One night Conquest shaped little pieces of soap to look like pills. He called over a nurse and told her he was killing himself and swallowed a big handful of fake pills. He then made believe he was convulsing and was rushed to the infirmary. Once he was there, he leapt from the stretcher and went apeshit, attacking nurses and doctors. He got some good shots in before they restrained him. Only a man named Conquest could pull that shit off. RELATIVIST WHITEY KILLER
Jamal had paranoid schizophrenia, and he hated white people. He countered every single thing I ever said to him by replying, “Yeah, but to what extent?” We didn’t get very far in counseling. EL GHOSTBUSTER
Alfredo was a Cuban refugee who started screaming in terror during an assessment, claiming in Spanish that the ghost of his murder victim was walking across the room even as we spoke. Alfredo was truly bonkers, but he was also a skillful and manipulative liar. To delay certain hearings, he had staff convinced that he spoke only his mother tongue. Then one day, seemingly out of nowhere and in perfectly coherent English, he asked me where I bought my sweater. MOMMA’S BOY
Tommy was only nineteen and sentenced to life for killing his mother. He ended up in the mental-health unit by faking a bunch of symptoms, which is a common way to avoid the much more dangerous general population. But unlike most criminals who fake delusions and hallucinations, Tommy went old-school and tried faking shit that hadn’t been diagnosed since the turn of the century, like hysterical blindness and glove paralysis. His acting was atrocious, and he soon confessed to his con. We let him stay for a while, though, because we knew he would be destroyed among the general population. Tommy was bright and sweet, and definitely my favorite patient ever. One day he wrote me a poem that included the line: “I don’t want the world to see me. Because I don’t think that they’d understand.” At first I thought it was poignant—until a coworker pointed out that Tommy had plagiarized Goo Goo Dolls lyrics. BOBBY RICHARDS
You get to meet a lot of fucking psychopaths when working in the mental-health unit of an East Coast maximum-security prison. All of the inmates I worked with were post-trial (already sentenced). Some were permanently in the mental health unit because they were found Guilty but Mentally Ill (which is different from Not Guilty by Reason of Insanity—that lands you in a forensic hospital). Other prisoners were sent to the mental-health unit because their “quirks” made it dangerous for them to be living in the general population. In fact, lots of the guys I saw were faking mental illness for that very reason, to be out of the snake pit. My duties included counseling, assessment and testing, conducting intake interviews with new arrivals, and saying “How-lee shit” to myself about 50 times a day. Here are just a few of the guys I miss the most: GAY JOHN
John was a twenty-year-old man, sentenced to 50 years for killing an acquaintance who had the audacity to assume John was gay. The victim made a pass at John, which he allegedly declined. Upon reflection, John became so enraged and obsessed that while the man was sleeping that night, John strangled him to death. John then strangled the victim’s cat to death because he believed the cat was gay too. When asked why he felt the need to murder the kitty, John replied, “I don’t do anything half-assed.” FARRAKHAN WHITEY KILLER
There are a few select men in prison who absolutely nobody fucks with—like a militant, Afrocentric, bipolar ex-boxer who legally changes his FIRST name to Farrakhan. This guy always seemed to be mopping, and that alone scared the shit out of me. CHESTER THE MOLESTER
Close your eyes and imagine what a cliché mentally ill, middle-aged pedophile looks like. See him? Bingo! Carl had thick glasses, crooked teeth, greasy hair, and remarkably poor hygiene. Jailed on several counts of child molestation, Carl was genuinely talented at making arts and crafts out of cigarette boxes and packing tape. He would cut a box into tiny triangles, laminate them, and weave them together with thin strands of tape. We all marveled as Carl showed us the picture frames and cup holders he created. We all cringed when he showed us the baby shoes he made with his scarily nimble fingers. You haven’t experienced creepy until you see a pedophile showing off a pair of handmade baby shoes. THE JERK-OFF
Some inmates pass their time trying to piss other people off. These are the kind of guys who try studying law while they’re locked up and then write letters to Norman Mailer about how fucked up the prison system is. Our most notorious letter-writer was a guy who penned a note to Bill Clinton about poor prison conditions, jerked off on said letter, and mailed it. It never made it out of the prison mailroom and the guy lost his television privileges for a month. Score one for the system. TICKLES THE CLOWN
Perhaps the purest psychopath I came across while working in the prison, Paul was a notorious child rapist who existed solely to get under people’s skin. His most shining moment was when he joyfully told a room of people evaluating him that he looked forward to getting out of jail one day and “working with children.” PIGPEN
Collins was the quintessential raving lunatic. The prototype. Like Charles Manson dipped in diarrhea. He was dirty, hairy, gaunt, wild-eyed, and covered in self-inflicted scars. He was also a chronicmasturbator with a history of throwing feces. Collins had the ability to hurt himself with any article of clothing he was given. One time he swallowed a bunch of buttons; another time he used the leg of his jumpsuit to strangle himself. As a result, he was forced to dress in a paper outfit—basically a big paper towel with a hole cut out for the head. Krazy with a capital K.