I Survived Prison: What Really Happens Behind Bars

As told to Abigail Pesta

I'm rolling up to Rikers Island, a notoriously violent prison in New York City, on a bus with about a dozen other women. My wrist is handcuffed to a lifelong drug addict whose stomach is distended from fibroids, she tells me. One of the ladies clearly hasn't bathed for weeks, and the smell is unbearable.

Simply boarding this bus was a feat in itself. If you think it sounds challenging to round up a group of hyperactive third-graders for a field trip, you should've seen the guards trying to get a bunch of loud-mouthed, drugged-out, furious female convicts to shut up, stand in line, and get on the bus.

A plain, redbrick building looms before me. I'm about to become a prisoner in a massive penitentiary, and I feel an overwhelming sense of dread. I'm surrounded by people who have been here before, who know the system, who know how to work the guards. But I know nothing. I'm thinking, I have to get through this. I have to stay safe. Stay alive. I tell myself that maybe someone in this prison needs me; perhaps that's the reason life has thrown me this curveball. For a moment, I think I hear a distant voice calling for help.

As the bus pulls to a stop, I try for about the millionth time to wrap my head around how I got here.

Just a couple of years ago, I was working as a Certified Financial Planner for American Express Financial Advisors and living with my cat, Figaro, in a leafy Brooklyn neighborhood. The trouble started when a relative recommended an investment opportunity in California — an operation that was buying foreclosed homes, fixing them up, then reselling them at a profit. He'd invested himself, and I followed suit.

At the same time, some of my clients started inquiring about real-estate opportunities, and I asked the compliance officer at American Express if I could mention this one. He said AmEx didn't deal with "hard property" real estate but that I could refer people independently if I filled out the proper securities forms. I did so, then told a few people about the investment, while advising them to do their own homework.

About a year later, in August 2005, I launched my own financial-planning business. Things went swimmingly for the first year, until investors — including members of my family and me — stopped getting any returns on that real-estate deal. So an attorney and I paid a visit to the owners of the California company. After our meeting, the attorney deemed the operation a scam and said I should report it to the authorities.

I did so immediately, in October 2006. A month later, several plainclothes officers confronted me on my street. "You're gonna let us in your apartment, or we're gonna beat the door down," one of them snarled. They confiscated my cell phone, computer, and files, while another set of police cleared out my office nearby. I was stunned, but I thought my stuff might help them nail the crooks.

Eight months later, when I was sitting in my office one morning in a favorite outfit — Ralph Lauren top, white pants, white heels — the police returned. I was arrested and accused of being part of a $1.6 million real-estate fraud, since I'd recommended the investment and had received standard referral fees. (Of course my family and I had lost a substantial amount of money in the con ourselves, but that didn't seem to matter.) After I answered a slew of questions from an assistant district attorney, my criminal-defense lawyer — who, by the way, was from the firm that had unsuccessfully defended Martha Stewart — advised me to agree to a deal with the DA. If I pleaded guilty, I'd get sentenced to six months in jail but could be out in four. "Four months is better than four years, which is what you could get if you go to trial and lose," my lawyer said. I hated the idea of making that deal, but since I was new to the legal field, I took his advice and signed the papers. That was January 2008.

For the next few months, while I awaited my sentencing, I moved my belongings into storage and stayed with friends, as I'd put my apartment on the market prior to the legal nightmare. I worked as a book consultant, since I'd written and published three finance books myself. I tried to do some research on Rikers, but Googling turned out to be a mistake. What popped up were reports of abuse, injustice, and rape, along with news of guards running an alleged prison fight club, in which inmates were forced to beat each other to a pulp. Nonetheless, any New York City dweller sentenced to less than a year on state charges gets sent there.

Terrified, I started preparing for hell. I sought advice from self-defense experts, and enlisted them to shout insults in my face so I could practice my response. I cut my hair and donated it to charity, because I'd been warned that prisoners could yank it, hard. I talked to my mom constantly. She believed I was innocent, as did my friends — at least, my true friends, who even wrote letters to the judge about me. A few people couldn't cope and dropped out of my life. Meanwhile, a tsunami of unflattering stories about me hit the media — the New York Times, New York Daily News, the Associated Press. The headlines were infuriating, and humiliating. I felt increasingly angry about pleading guilty.

In June 2008, I went to a criminal courthouse in downtown Manhattan to be formally sentenced. The courtroom looked like something straight out of Law & Order, with old-fashioned wood-paneled walls, wooden pews, and a sign above the judge's head that said "In God We Trust." I stood before the judge and asked her if I could withdraw my guilty plea. The answer: No.

That same day, I said good-bye to my family, my cell phone, my normal life. Then I was handcuffed and escorted to a dingy basement room called "the bridge," where I waited with a bunch of prostitutes and drug addicts for the bus to Rikers.

When I replay it all in my mind, it seems like a bad movie or a nightmare — not anything real. But the reality sets in as soon as I step off the bus at Rikers, where the indignities begin promptly. For starters, I'm told to strip naked and squat — the idea being that any contraband I might be hiding inside me will tumble out. Then the guards make me sit in a computerized chair called the B.O.S.S.; the chair seems to be doing an X-ray of my insides to detect anything I might have swallowed in order to conceal it. I tell myself not to take any of this personally, but it's hard not to let it mess with my mind. I feel like I'm in a foreign country where I don't know the language or the rules, and no one wants to help. Anything I say can be misinterpreted. I'm afraid to ask even the simplest questions. Guards and inmates are staring at me; they know I'm new here. I have to stay alert.

I undergo a series of medical tests (for tuberculosis, HIV) for the next six hours. Then I put on a dark-green jumpsuit and head to my new home: a minuscule, private cinder-block cell (about eight feet by three feet) that contains a metal cot with a block of foam on top and a sheet but no pillow. There's a white porcelain toilet and sink right out in the open; I'm handed a towel, a bar of scratchy white soap that's more like bleach, and half a roll of toilet paper. No hot water. A tiny window looks out onto a parking lot.

I sit on the cot, take a deep breath, and thank God I'm alive; I've made it this far. I think, Whatever I'm supposed to do here, let me do it well. I remind myself that I can survive by becoming invisible: I will not act superior, or fearful. I'll follow directions, and I won't ask any questions of anyone. By this time, it's 4 in the morning, and I've been up for more than 24 hours. Breakfast will be served in one hour. I lie awake, not sure if I'm allowed to sleep; I'm afraid of getting in trouble if I miss breakfast.

After a week marked by entire days of keeping mostly to myself, I move to a dorm with 50 other women. The beds are crowded onto an open floor surrounded by tan Sheetrock walls. Most of the women here have aligned themselves with people from the housing projects they come from, so there are Latin factions, African-American ones, and so forth. I keep my head down, and pray.

There are regular confrontations. One woman randomly decides she doesn't want me to use the phone and tries to pick fights with me in front of the guards when I call my mother. One day she says, unprovoked, "Did you call me an idiot?" I reply that I don't say that type of thing, and luckily, the situation doesn't escalate. I know I have to stand up for myself and not show fear.

One evening, I witness a fight just before dinner. We're all assembling in the dormitory, with the guards barking at us to "shut up and line up," as usual. Suddenly, one woman flies at another, punching her everywhere — in the face, the gut. I've never seen a fistfight in real life, with two people trying to kill each other. Another woman jumps in, and the trio turns into a tornado, careening around the room. The guards gradually isolate them, ordering everyone else out. I imagine that the women were sent to solitary confinement in a dreaded place known as "the bin."

The most threatening person is a brute of a woman who leers at me menacingly one night in the communal showers. I know she wants to rape me; I've been warned of the signs. Rumor has it that another woman was recently raped by three female inmates in the high-security wing, which is a heavily patrolled area, so presumably the guards knew what was happening. In my case, a fellow inmate comes and stands defiantly by my side in the shower, and the bully backs off.

I lose 14 pounds in the first six weeks, due to stress and also to the fact that I've been an organic vegetarian for years. I have Crohn's disease, a serious digestive disorder, and my diet has helped me keep it under control. But there is hardly anything green or even remotely fresh served in jail. Meals mostly consist of slices of bread and turkey patties or fried chicken quarters, which the prisoners like to refer to as "seagull meat." I don't eat much, to the delight of my fellow inmates, who constantly ask for my leftovers. There's also a commissary, which is stocked with cookies, candy, and Kool-Aid packets that inmates can purchase once a week. Only a prison dietitian knows of my condition. Her advice? "You have to find a way to survive here."

Our days are extremely regimented; we're counted several times by guards changing shifts so they can make sure we're present, and alive. There's a law library and an outdoor area for exercise, such as jump rope. A TV blasts shows like Jerry Springer and Maury Povich in a common room. We're allowed to make the occasional cup of tea, but only if the entire dorm is clean, which is a regular source of friction. Religious services are popular, with prisoners frequently spouting, "Only God can judge." All of us have jobs; I make 39 cents an hour working in the prison garden, as part of a training program provided by the Horticultural Society of New York. Nighttime is a cacophony of raucous arguments among all the wound-up women who have been consuming sugar and starch all day, with the guards threatening to flip on the fluorescent lights if people don't pipe down.

As time creeps by, what keeps me sane is the continuing belief that I'm here for a reason, that I might be able to help someone. Gradually, I do. I manage to teach a woman from Trinidad to read, and I show others how to do yoga. I hold poetry readings with the woman who bunks next to me, an African-American Muslim who has been homeless at times. When I describe how I'd once heard someone calling for help, she says it was her.

On the final day of my ordeal, in October 2008, my mother and a dear friend escort me out into a bright, brisk fall afternoon. At this point, I've contracted a full-body yeast infection called candida, but I've never felt better — or freer — in my life. With my 40th birthday just around the corner, I feel oddly proud of myself. I'm tougher than I realized, and now I know I can win the respect of people from worlds very different from my own. I can keep a positive outlook in the worst of circumstances. Ironically, I have my experience at Rikers to thank for that knowledge. As one of the guards once said to me, "If you can survive this place, you can survive anything."

For more on Jennifer Wilkov, go to jenniferswilkov.com.

CNBC's Scott Cohn reports on what awaits white collar criminals when they enter prison, with Jennifer Wilkov, former Rikers Island inmate and Abigail Pesta, Marie Claire.