This story is over 5 years old.

The Hopelessness Issue

Don’t Get Caught

When I take a serious look around, it dawns on me how much wasted potential there is in prison, how many people are living with regrets who will never have a chance to make good on them. It’s way too late.

Me in the present, enjoying the park in Williamsburg, Brooklyn, where I used to picnic when I was on work release.


’d been involved in selling drugs since I first smoked weed when I was 13. It just made sense to me that in order to have the money to use drugs, I’d have to sell some, too. I never thought I was doing anything wrong—my entrepreneurship put smiles on a lot of faces, and I did it better than most people ’cause I showed up on time and wasn’t a greedy, lying scumbag. I did abuse my stash pretty frequently, but I had enough self-control to avoid going off the deep end.


As a kid, I attended elite prep schools, played hockey year-round, and wound up getting accepted into Skidmore College, where, smooth as silk, I kept selling narcotics, mostly to my fellow students. Soon, I was HOOKED, living lovely off all that drug loot. I drove all around the Northeast like a madman, bartering and hustling coke, weed, X, shrooms, and whatever else seemed like a good flip. (I stayed away from dope and crack, though—you have to draw the line somewhere.)

I was so cocky—I never actually thought the pork-chop patrol would come after me. I ignored the illegality of what I was doing and didn’t care about my well-being enough to investigate or even pay attention to the laws. But as I soon learned, the law was paying lots of attention to me.

On a seemingly normal Friday night in February 2004, I was outside a Barnes & Noble with my older brother and his son when I got tagged by an undercover cop who looked like an upstate trailer-park stick-up kid. In retrospect, I wish he had robbed me for all my money instead of cuffing me in front of my six-year-old nephew. At that moment, my brain was spiraling through a million made-up explanations for my arrest instead of accepting the nightmarish reality of what was about to happen next. The pigs had a search warrant, and they took me back to my crib to rifle through my head stash, which was substantial enough to get me charged with five felonies and, potentially, 12 to 25 years in prison. I was 23 years old.


I spent the night in county jail and then, thankfully, was released on bail to await my trial. At the time, I was in my last semester of college and had been as excited as a nip-sucking piglet to finally graduate with all of my peoples. The future was so bright, and unlike most of my fellow students, I was in the black: I had a ton of money saved. I had already booked my plane tickets and hotel reservations to go to Italy with my girlfriend. But not anymore. Whatever the outcome of the trial, I knew my parents would be devastated (way more than I was), and I’d probably be kicked out of school.

I ended up taking a plea bargain. I was sentenced to three to nine years in state prison. My lengthy sentence was at least partially a case of being in the wrong place at the wrong time—’04 was an election year, and the politicians in Saratoga Springs, where I was living and dealing, thought the town had a drug problem. The district attorney who prosecuted me probably figured nabbing a college student “involved in a drug-trafficking ring from New York City” (as the local paper referred to me) was a good demonstration that the city was tough on crime. They made an example out of me.

I took the plea deal in August, and they told me I was going to jail in October. Because I was at home, living in my own apartment, I spent that summer in an awkward sort of hell—I was technically free, but soon not to be. Every day that passed inched me closer to The End. It was such an awful countdown—never before or since in my life have I wanted time to stand still.


When the morning of that loathsome day arrived I was already running late, stumbling out of my girl’s apartment, hungover and sleep-deprived. I left my bonerabelle sobbing uncontrollably in the bed. She couldn’t handle going to court and watching the police take me away. We’d been together a couple years, and this was the most horrible way imaginable to say good-bye. Only death would’ve been worse.

I found my parents parked on the street, waiting, already lockjawed with tears in their eyes. They were so caring that they had even temporarily moved to Saratoga Springs, renting an apartment for a few months to watch over me while I was out on bail, making sure I didn’t do anything stupid before I was sent away, which I probably would have if they weren’t there. I still cringe over the pain I put my father and mother through. I felt like the Human Turd.

My senior-year yearbook picture. I attended Millbrook School, near Poughkeepsie, New York.


efore my trial, while I had been awaiting sentencing in the county jail, I had met a few small-time thugs who tried to scare me with the classic prison-shower scenario: “So you’re in the shower and Bubba steps to you, blade in hand, and says, ‘I’m either leaving here with blood on my dick or blood on this banger. What’s it gon’ be?’” But this never happened. Instead, I ended up serving a total of eight months in a “boot camp” in upstate New York for first-time nonviolent offenders, which they call “shock incarceration.” I received the same three-to-nine-year punishment as 50 Cent did for similar drug charges and graduated from the same program.


I wasn’t raped there, but I did nearly have my ass beat. A shock inmate is on his feet and forced to do some sort of nonsense for 18 hours a day, overseen by a bunch of obnoxious hillbilly drill instructors screaming taunts like, “Shut your cock polisher, you sperm-burping bitch!” Lots of these wannabe hardasses aren’t educated, nor do they have any sort of military background; they’re just good ole boys who enjoy fuckin’ with city slickers. A few were legit, good people, but others were awful pieces of sadistic shit who abused their power beyond belief. I saw inmates get choked, punched in the face, and bullied until they cried. Still, I managed to keep a low profile. I also made a couple close friends from within my platoon, which helped the time pass. But in truth, there really isn’t a lot of free time to kick the willy bobo when you’re being harassed and made to do busywork all day and night.

Shock inmates are not allowed books, games, music, or packages from home—the idea is that, much like a military recruit, a new inmate is stripped of everything and then rebuilt. The goal is to change an individual with criminal tendencies before it’s too late. I don’t think it did much for me, maybe because I dealt with the monotony by acting like a robot and didn’t pay much attention. I exerted the bare amount of energy needed to slide by without anyone bothering me. I remember largely being concerned with the sad fact that my girlfriend, too ashamed to give me a proper dismissal, stopped visiting and writing me after only three or four months. Later, I received a letter from a friend describing how he walked in on her slutting it up with a dude I thought was a low-life who probably had a case of explosive herpes. It doesn’t seem as devastating today, but for three or four months I spent at least ten hours a day in a fury over this broad. I couldn’t get it out of my head. All my plans down the drain—a for-the-most-part-excellent two-year romance, my first true love, was now unraveling while I was powerless in prison. Shock ruined a lot of relationships. We were only allowed ten minutes of phone time twice a month, whereas in a normal jail you can pretty much talk whenever the phones are free. All I had was a pen and paper. The three or four letters a week my baby got from me definitely would’ve made her cry—but I still don’t know whether she ever bothered to read them.


I remember being a goofy spaz as a kid. Later, drugs would calm me down.


 got out of jail just in time for my 25th birthday in 2005, and within two or three weeks I was making trips back down to the Bronx to pick up coke and E. I don’t blame it on anyone but myself, but I was helped back into the drug-dealing world by a girl I had known before I went to prison, who approached me at a bar one night, explaining she’d always had a crush on me. It was a good enough reason to wind up naked in bed with her. This bona-fide-sexy stripper broad, whom I started dating shortly afterward, encouraged me to deal, and soon I was making a couple grand every week. Plus, I was always invited to parties—more often than not ones with a bunch of mostly naked cokehead strippers sniffin’ and cryin’ about how their stepfathers raped them or their moms sold their naked prepubescent bodies to a crack dealer. Ever since those nights, I haven’t looked at strippers the same or been enticed to hit up a titty bar even once. There was not much time to think—even when I wanted to—and I thrived off the chaos. It was a very poor decision to go back to that life so quickly. I should’ve given honesty and hard work a chance… or at least waited until I finished up parole to start dealing again.

And of course, I ended up getting caught, in February 2006, with my crazy sexy baby as my codefendant. It is a shameful experience to get busted a second time; any good will you’ve earned is immediately squandered because you’re letting people down and affirming all the naysayers.


This time around, though, we decided to fight the charge in court, ’cause the cops searched us illegally. Then, as we were ready to go to trial, my girlfriend was arrested again while on bail for a slew of things and decided to turn on me—she signed a written statement that contained some truth and a lot of complete fabrications that made me out to be a drug-pushing woman beater. After that, I was screwed, so I had to cop out and take a parole violation, which put me in a bad spot. I had to serve two more years of my original sentence inside, and I bounced around from Saratoga County Jail to “correctional facilities” in Lyon Mountain and Hale Creek. I did a whole tour of upstate New York.

In Saratoga, time sometimes moved very slow, ’cause we were trapped in one big cellblock all the time. During the winter, we didn’t even get outside for an hour a day, so I didn’t see the sky for months. Lyon Mountain, which recently closed, was a pretty cool minimum-security prison where I did some work-crew stints mowing lawns, shoveling snow, and other grounds-maintenance shit. Hale Creek focused on drug programs, so I spent a lot of hours in excruciating group-therapy sessions. The only entertainment was that one of our counselors was making out with inmates, which caused quite a ruckus (the counselor was eventually fired).

After graduating from Hale Creek, they shipped me down to Manhattan for work release. Work release is for nonviolent convicts and allows for work furloughs during which, after displaying good behavior for a few months, you’re allowed to spend some nights at home in your own bed. I spent nearly two years at a work-release facility in Harlem, employed at a nonprofit in downtown Manhattan as an in-house writer. My duties were beyond dull, but I was BLESSED to have a decent job. And my situation was more surreal than ever—I was out in the real world working like a seemingly normal citizen, like the Burykill I might’ve been if I’d never started dealing. But after work, instead of going out with coworkers, having drinks at the bar, and gettin’ my dizzle stizzled by the secretary, I was taking the train so I could be back at jail by 7 PM, where I had to then endure more group therapy with a bunch of convicts. Alongside 80 obnoxious dudes, I’d spend my nights sleeping in a room on an uncomfortable metal rack with an inch-thick “mattress” that looked like something a bird would peck together out of recycled cardboard boxes and other trash.


I earned some privileges as time went on, basic stuff like keeping my paychecks (when I started, they’d give me 15 percent of what I earned as a stipend and put the rest in an account I couldn’t touch until I was granted release) and renting my own apartment. I was trying hard to live the normal life, but I had this awful and embarrassing secret: I was spending a couple nights in prison each week. During that time I had bagged a couple pussycats, only to freak ’em out with the fact that I was required to hang out in prison every so often. Then I met my current girlfriend, who, against all sound judgment, proved to be addicted to what my dick did to her just enough to fall in love with me. Yet despite the lustrous cloud of affection filling our hungry nostrils, she couldn’t tell her parents why I had such a weird and unpredictable schedule. The stress was killing me. After a year of this, I managed to get 7-0 status, which meant I was allowed to sleep at my place every night, although I still had to spend a few hours in the facility twice a week. Then came my parole hearing.

A photo of me in prison from ’07. These pictures with the hand-painted backdrops are called “click-clicks,” and inmates love ’em. I sent this one out to females I was trying to impress.

I went before the parole board on the morning of July 2, 2009, a Thursday. I was pretty confident in my chances of going free—I acted humble, admitted my crime, and expressed remorse and disgust at the way that I used to live. I even lauded the rehabilitation I received while incarcerated. I had been working at the same job for the whole 18 months, and I had received promotions and raises that I had documented for the board to review. But when I brought them up during the interview, it seemed as though no one had read my bosses’ letters that vouched for my good character, at least judging from the questions the board members asked. Sometimes the Division of Parole makes decisions arbitrarily, or at least it seems that way for the poor shitheads on the receiving end of their life-wrecking judgements. Despite my best efforts, the board told me that I’d be on work release for the next two years. Worse yet, they revoked my 7-0 status and started taking my paychecks again, to the point where I couldn’t pay rent. The board claimed they weren’t happy with the interview given during the hearing. Basically, they thought I was lying about something. They also said that if I was released into the free world I would likely commit the same crime again. Although that had happened once, for 18 months I had been in the free world with absolutely no police contact, no getting into trouble. I was pissed.


So of course, being who I am, I started selling weed, coke, and ecstasy again and wound up moving into the living room of a friend, a friend who happened to do quite a bit of the drugs I was selling. It was fun, but not the ideal situation for someone being closely supervised by three different branches of the New York State Department of Corrections. Either way, I was beyond bitter and started getting fucked up on the regular. I never claimed to be the tastiest cracker on the counter, but I was stale as hell that summer. I got dumber than dumb, retarded-level-IQ idiotic.

A couple months after getting hit at the parole board, I pissed dirty at the work-release facility. They were on some no-tolerance bullshit: “You’re lucky to be here, there’re thousands of inmates upstate ready to take your spot… SORRY.” They didn’t take into account that I’d been doing the right thing for 20 months, or at least avoided getting caught for anything illegal.

After pissing positive, I was allowed one last visit from my girlfriend in the work-release jail while I was waiting to get shipped north. We cried bona fide tears of pain, anguish, and sorrow.

It was just so fuckin’ stupid, sad, and pathetic that I was about to give up months of hard-earned life just ’cause I wanted to party. We sat there holding hands like a couple of dummies; I’ll never forget the misery of her crying as I fought back guilty tears of shame, figuring I wouldn’t be butt-nekkid with my bonerabelle for about a year—I was HURTING, thinking she wouldn’t make it, about the plethora of hogs desperate to fuck her away from me. Turns out a year was wishful thinking on my part—somehow it became 24 months before I was allowed to frolic nekkid inside her delectable pusshole. I don’t care who you are or where you are, that’s one stiff punishment for just having a dirty dick.


The upstate prison I was sent to, Riverview, had a view of the distant lights of the Ogdensburg-Prescott International Bridge, which crossed over the river and into Canada. It was early on during this time that I had a feeling, some sort of premonition, that I would become a writer. I was in the box for that first month after the dirty urine test, sending letters to my girl and my parents telling them that I was just going to write the bid away, and that I wouldn’t need much from them (yeah, right).

I knew that at this point I was such a selfish piece of shit and lower than low—the best I could do was to try to put those feelings onto paper in an attempt to figure out how someone so seemingly intelligent and (relatively) normal like me could do this to himself. The answer is still elusive. Clinically speaking, I suffer from the disease of addiction, but I say fuck that! I’ll stay in denial. The only affliction I will accept is the one that causes me to break out in cuffs, one where the only place I can recuperate—according to the law—is behind bars.

Prison has taken so much away from me, and so I have vowed to use my experience to get something back.

It ain’t easy bein’ sleazy.


ince my first arrest, I’ve gone back to jail four times. Sometimes, obviously, it was because I was acting the uncouth fool. But other times I got caught doing things that the paroled are not allowed to partake in but ordinary nonoffenders take for granted. And they all sent me to prison, no questions asked: drinking a beer, driving a car, being out past curfew.


In total, I’ve spent six years behind bars, and today I’m free but still have two more years of parole. Do my actions really merit this much time and money spent watching me? In the minds of many sensible Americans, I am not even a criminal—I never physically harmed anyone, I just sold some stuff the Man didn’t want me to sell—but to this day I can be locked up at any time for doing things that an average citizen wouldn’t even get ticketed for.

For instance, earlier this year I went back in because a few city cops thought I was breaking into a car when, in reality, a friend was fixing the window of my car. Once the ball-lickin’ porkchop ascertained I was on parole for drug charges, he decided to illegally search me and my vehicle. He came up empty-handed and let me go but notified my parole officer that he “interviewed” me, and I subsequently got arrested because all of this happened just after my 9 PM curfew. What fucked me is that whenever a parolee has contact with the police he is supposed to notify his PO, but it was my honest misunderstanding that this only applied if I got a ticket or was arrested. The cops actually apologized for searching me, but according to parole, fixing my car window minutes past my curfew was a serious enough offense to send me to county jail for two months.

And so I entered my third decade on the planet trapped in a room with 59 other men who had been stripped of their ability to achieve anything. Quite a few of them will never be coming home. Yet every two years at their parole hearings they will still drive themselves crazy clinging to the hope that they will see the world again and use every trick in the book to try to get out. Then there are those of us—like me—whom the “lifers” want to kill, ’cause we get our shot back in the free world and within a matter of months we’re back in jail. It’s a pretty common phenomenon: Out of the 2 million Americans on parole today, according to the good ole Department of Justice, about 100,000 per year land back in jail for small violations. When I was locked up, I remember one dude in particular—a guy who’d gotten blackout drunk and accidentally killed a friend by crushing his throat—who really didn’t like us failed parolees. He freaked me out right after I arrived at Riverview by showing me all his paperwork, basically bragging that he was a true killer. When he learned that I had just fucked up my work release he grew red with rage, and I was sure I was next on his hit list.

That look, the burning contempt in an eternally condemned man’s eyes, drove it home for me: I need to live desperately and carefully, doing whatever it takes to avoid the stinkin’ clink-clink. It’s essential to find ways to have fun in prison, to somehow maintain your sanity. But when I take a serious look around, it dawns on me how much wasted potential there is inside, how many people are living with regrets who will never have a chance to make good on them. It’s way too late.

All of this isn’t just a lesson on how to deal with prison. It’s a lesson on how to deal with life—one that I’m guilty of forgetting all the time. It’s been almost a decade since I’ve been able to find happiness within myself, and before that I was usually happy for the wrong reasons. Now I just need to convince my girl to be patient a little longer, to just chill and be quiet while I try to make good things happen. As long as I’m not locked up, there’s always hope that I might win the lotto, or that my girl might introduce an exotic bird into the bedroom. That shit is never going to happen if you’re in jail.

Portrait by Christian Storm

Want more from Bert Burykill? Check these out:

Pissin’ Out the Pain

'Ruff Buttlove' and Other Prison Raps

Why Can't I Vote?