My Friend Leonard

James Frey - Author

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ISBN 9781101217375 | 416 pages | 16 Jun 2005 | Riverhead | 18 - AND UP
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The New York Times bestselling follow-up to the #1 New York Times bestseller A Million Little Pieces-the heartrending story of a friendship between a newly-sober James and the charismatic, high-living mobster he met in rehab, Leonard.

A Million Little Pieces was the first Oprah Book Club pick by a living author in over two years. It instantly became a #1 New York Times bestseller, a #1 USA Today bestseller, and a #1 Publishers Weekly bestseller, with over 1.7 million copies in print.

My Friend Leonard picks up right where Pieces leaves off. A New York Times bestseller in its own right before the Oprah pick, My Friend Leonard is James Frey's story of his friendship with Leonard, the larger-than-life mobster who "adopted" James as he left rehab. Leonard, who offers James lucrative-if illegal, mysterious, and slightly dangerous-employment when he needs it. Leonard, of the secret deals, of the surprising passions that belie his violent career choice, of fantastic generosity and ferocious loyalty. Leonard, who has been holding on to some remarkable secrets, and who has invested in their friendship more than James could ever imagine.

My Friend Leonard is, at its core, about the responsibility that comes with loving someone and going out on any number of limbs to care for them. And it is a book that proves that one of the most provocative literary voices of his generation is also one of the most emphatically human.

On my first day in jail, a three hundred pound man named Porterhouse hit me in the back of the head with a metal tray. I was standing in line for lunch and I didn't see it coming. I went down. When I got up, I turned around and I started throwing punches. I landed two or three before I got hit again, this time in the face. I went down again. I wiped blood away from my nose and my mouth and I got up I started throwing punches again. Porterhouse put me in a headlock and started choking me. He leaned towards my ear and said I'm gonna let you go. If you keep fighting me I will fucking hurt you bad. Stay down and I will leave you alone. He let go of me, and I stayed down.

I have been here for sixty-seven days. I live in Men's Module B, which is for violent and felonious offenders. There are thirty-two cells in my module, thirty-two inmates. At any given time, there are between five and seven deputies watching us. All of us wear blue and yellow striped jumpsuits and black, rubber-soled slippers that do not have laces. When we move between rooms we walk through barred doors and metal detectors. My cell is seven feet wide and ten feet long. The walls are cement and the floor is cement and the bed is cement, the bars iron, the toilet steel. The mattress on the bed is thin, the sheets covered with grit. There is a window in my cell it is a small window that looks out onto a brick wall. The window is made of bulletproof glass and there are bars on both sides of it. It affords me the proper amount of State required sunlight. Sunlight does not help pass time, and the State is not required to provide me anything that helps pass time.

My life is routine. I wake up early in the morning. I brush my teeth. I sit on the floor of the cell I do not go to breakfast. I stare at a gray cement wall. I keep my legs crossed my back straight my eyes forward. I take deep breaths in and out, in and out, and I try not to move. I sit for as long as I can I sit until everything hurts I sit until everything stops hurting I sit until I lose myself in the gray wall I sit until my mind becomes as blank as the gray wall. I sit and I stare and I breathe. I sit and I stare. I breathe.

I stand in the middle of the afternoon. I use the toilet and I drink a glass of water and I smoke a cigarette. I leave my cell and I walk to the outdoor recreation area. If the weather holds, there are prisoners in the area playing basketball, lifting weights, smoking cigarettes, talking. I do not mingle with them. I do not participate in their approved activities. I walk along the perimeter of the wall until I can feel my legs again. I walk until my eyes and my mind regain some sort of focus. Until they bring me back to where I am and to what I am, which is an alcoholic and a drug addict and a criminal. If the weather is bad, the area is empty. I go outside despite the weather. I walk along the perimeter until I can feel and remember. I am what I am. I need to feel and remember.

I spend my afternoons with Porterhouse. His real is name is Antwan, but he calls himself Porterhouse because he says he's big and juicy like a fine-ass steak. Porterhouse threw his wife out the window of their seventh floor apartment when he found her in bed with another man. He took the man into a field and shot him twelve times. The first eleven shots went into the man's arms and legs. He waited thirty minutes to let the man feel the pain of the shots, pain he said was the equivalent to the pain he felt when saw the man fucking his wife. Shot number twelve went into the man's heart.

From three o'clock to six o'clock, I read to Porterhouse. I sit on my bed and he sits on the floor. He leans against the wall and he closes his eyes so he can, as he says, do some imagining. I read slowly and clearly, taking an occasional break to drink a glass of water or smoke a cigarette. In the past twelve weeks we have worked our way through Don Quixote, Leaves of Grass, and East of Eden. We are currently reading War and Peace, which is Porterhouse's favorite. He smiled at the engagement of Andrei and Natasha. He cried when Anatole betrayed her. He cheered at the battle of Borodino, and though he admired the Russian tactics, he cursed while Moscow burned. When we're not reading, he carries War and Peace around with him. He sleeps with it at night, cradles it as if it were his child. He says that if he could, he would read it again and again.

I started reading to Porterhouse the day after he hit me with the tray, my second day here. I was walking to my cell and I had a copy of Don Quixote in my hand. As I passed his cell, Porterhouse said come here, I wanna talk to you. I stopped and asked him what he wanted. He said he wanted to know why I was here and why a County Sheriff would give him three cartons of cigarettes to beat my ass. I told him that I had hit a County Sheriff with a car going five miles an hour while I was drunk and high on crack and that I had fought several others when they tried to arrest me. He asked if I had hit the man on purpose. I told him I didn't remember doing it. He laughed. I asked him why he was here and he told me. I did not offer further comment. He asked what the book was and I told him and he asked why I had it and I told him that I liked books. I offered to let him have it when I was done with it and he laughed and said I can't read motherfucker. Fucking book ain't gonna do me no good. I offered to read to him. He said he'd think about it. A couple of hours later he showed up and sat on my floor. I started reading. He has been here every day since.

At six o'clock, I walk with Porterhouse to dinner, the only meal of the day that I eat. It is usually foul, disgusting, almost inedible. The meat is mush, the bread stale, potatoes like water, vegetables hard as rock. I eat it anyway. Porterhouse eats seconds and thirds and fourths, which he takes from the trays other prisoners. He offers to get food for me, but I decline. When I am finished eating, I sit and I listen to Porterhouse talk about his upcoming trial. Like every other man in here, regardless of what they might say, Porterhouse is guilty of the crimes that he has been accused of committing. He is going to trial because until he is convicted, he will stay here, at county jail, instead of doing his time in state prison. Jail is a much easier place to live than prison. There is less violence, there are more privileges, most of the prisoners know they are getting out within the next year and want to be left alone. Once they're gone, they don't want to come back. In prison, there are gangs, rapes, drugs, murder. Most of the prisoners are in for long stretches and will most likely never be free. If they are ever free, they will be more dangerous than they were before they were imprisoned. They could give two fucks about rehabilitation, they need to survive. To survive they need to replace their humanity with savagery. Porterhouse knows this, but wants to remain human for as long as he can. A guilty verdict is coming his way, but until it does, he will stay here. He will remain a human being.

After dinner I go to the payphone. I dial a number that was given to me by my Friend Leonard. The number allows me to make free long distance phone calls. I do not know where Leonard got the number, and I have never asked him. That has always been my policy with Leonard. Take what he offers, thank him for it, do not ask questions. Leonard is what I am, an Alcoholic and a Drug Addict and a Criminal. He is fifty-two years old and he lives in Las Vegas, where he oversees his organization's interests in a number of finance, entertainment and security companies. We do not discuss his business. I do not ask questions.

I always call Lilly first. Lilly with long black hair and pale skin and blue eyes like deep, clean water. Lilly whose Father deserted her and whose Mother sold Lilly's body for drugs when she was thirteen. Lilly who became crackhead and a pillpopper and hitchhiked across the country on her back so that she could escape her Mother. Lilly who has been raped and beaten and used and discarded. Lilly who is alone in the world except for me and a Grandmother who has terminal cancer. Lilly who is living in a halfway house in Chicago while she tries to stay clean and waits for me to be released from this place. Lilly who loves me. Lilly who loves me.

I dial the number. My heart starts beating faster. I know she's sitting in a phone booth waiting for my call, but my heart beats faster anyway. She picks up on the third ring. She says hello, dear boy, I say hello, dear girl. She says I miss you and I say we'll see each other soon. She asks me how I am and I tell her that I'm good. She's upset that I'm here and I don't want her to worry, I always tell her things are good. I ask her how she is and her answers vary from day to day, hour to hour, minute to minute. Sometimes she says she feels free, which is a feeling she has rarely felt but has always sought. She feels like she's getting better and healthier and can put her past behind her. Sometimes she says that she feels fine. That she is getting by and that is enough. That she's off drugs and has a roof over her head, that she's fine. Sometimes she's depressed. She feels like her Grandmother is going to die and I am going to leave her and she is going to be alone in the world, which is something she says she cannot handle. She says there are always options, she'll weigh them when the time comes to weigh them. Sometimes she feels nothing. Absolutely nothing. She doesn't talk she just breathes into the phone. I tell her to hold on, that she'll feel again, feel better again, feel free again, I tell her to hold on. She doesn't talk. She just breathes into the phone.

I met Lilly and Leonard five months ago. I was a patient at a drug and alcohol treatment center. I checked in after a ten year bout with alcoholism and a three year bout with crack addiction, which ended when I woke up on a plane after two weeks of blackness and discovered that I had knocked out my front four teeth, broken my nose my eye socket, and torn a hole in my cheek that took forty stitches to close. At the time, I was wanted in three States on drug, drunk-driving and assault charges. I didn't have a job or any money and I was nearly dead. I didn't want to go the treatment center, but I didn't have any other options. At least not options I was ready to accept.

I met Lilly on my second day. I was standing in line waiting for detoxification drugs and she was standing in front of me. She turned around and she said hello to me and I said hello to her and she asked what happened to my face and I shrugged and told her I didn't know. She laughed. I saw her and spoke to her later that day and the next and the next. The treatment center had a policy against male/female relationships. We ignored the policy. We talked to each other, slipped each other notes, met each other in the Woods that were part of the center's grounds. We helped each other and understand each other. We fell in love with each other. We are young, she is twenty four and I am twenty three, we fell in love. Neither of us had felt anything like what we felt for one another and we agreed that we would stay together and live together when we left the treatment center. We got caught with each other and we paid for the violation of the Center's rules. Lilly left the center and I went after her. I found her selling her body for crack and I brought her back. I left a week later and I came here. Lilly stayed for nine more weeks and has been at the halfway house in Chicago for a month. When I leave here, I am going to meet her. We love each other. We are going to stay with each other.

I met Leonard three days after I met Lilly. I was sitting by myself in the cafeteria eating a bowl of oatmeal. He came to my table and accused me of calling him Gene Hackman. I didn't remember calling him Gene Hackman, which made him angry. He told me that if I called him Gene Hackman again, there was going to be a problem. I laughed at him. He did not take kindly to my laughing and he threatened me. I laughed again, called him an old man, and told him if he didn't get out of my face, I was going to beat his ass. He stared at me for a minute. I stared back. I stood up and told him to get the fuck out of my face or prepare to get his ass beat. He asked me my name and I told him. He told me his name and asked me if I was fucked-up. I said yes, Leonard, I'm fucked-up bad. He offered me his hand and said good, I'm fucked up too and I like fucked-up people. Let's sit and see if we can be friends. I took his hand and I shook it and we sat down and we ate together and we became friends.

Over the course of the following two months, which is how long I was at the treatment center, Leonard became my closest friend. When I walked out of the center shortly after finishing the process of physical detoxification, Leonard walked out after me. I told him to leave me alone, but he wouldn't do it. He followed me. I knocked him down, and he got up. I knocked him down again and he got back up again. He told me that he wasn't going to let me leave, and that if I tried, he would have me found and brought back. He told me it didn't matter how many times I left, he would have me brought the fuck back every single time. I looked into his eyes and I listened to his words. He is thirty years older than me but he is what I am, an alcoholic and a drug addict and a criminal. His eyes and words held truth. I went back to the center and I stayed at the center. I was leaving because I wanted some liquor and I wanted some crack. I stayed because of Leonard.

For whatever the reasons, and I do not know all of them, whenever I needed something or someone, Leonard was there. He watched over me and protected me. He helped me reconcile with my family. He gave me the best advice that I was given while I was at the center, which was to hold on. No matter how bad or difficult life becomes, if you hold on, hold on to whatever it is you need to hold on to, be it religion, friends, a support group, a set of steps, your own heart, if you hold on, just hold on, life will get better. He encouraged me to be with Lilly. He told me to forget about the fucking rules, that love doesn't come around that often, and when it does you gotta take it and try to keep it. After Lilly left, she needed money to come back and stay at the center. Her Grandmother didn't have any more money. She had spent what she had to put Lilly there the first time. She didn't qualify for any of the financial aid programs. I didn't tell Leonard about Lilly's problems and I didn't ask him for help. He had done enough for me.

The morning he was leaving he asked to speak to me. I went to his room and he handed me a card. It had five names and five phone numbers on it. All of them were his, he said he used different names in different places. He said call if you need anything, doesn't matter what it is or where you are, just call. I asked him why there were five numbers and five names on the card and he told me not to worry, just call if I need anything. After he gave me the card, he said he had something he wanted to talk to me about. I said fine, talk. He looked nervous, which I had never seen before. He took a deep breath. He said Kid, I have always wanted to be married and I have always wanted to have children. More specifically, I have always wanted to have a son. I have been thinking about this for a while now and I have decided that from now on, I would like you to be my son. I will watch out for you as I would if you were my real son, and I will offer you advice and help guide you through your life. When you are with me, and I plan on seeing you after we both leave here, you will be introduced as my son and you will be treated as such. In return, I ask that you keep me involved in what you are doing and allow me to take part in it. If there are ever issues with your real Father, I will insist you defer to and respect him before me and over me. I laughed and asked him if he was joking. He said that he wasn't joking, not even close. I warned him that I tended to cause a lot of problems for the people in my life, and that if he could deal with that, I'd be happy to be his son. He laughed and he hugged me. When he released me he said he wanted me to go to jail and do my time and protect myself. He said not to worry about Lilly that she was going to be taken care of, that her financial issues had been resolved, that he hoped someday she would be better. I tried to object, but he interrupted me. He said what is done is done, now say thank you. I said thank you and I started to cry. I hoped that someday she would be better.

When I'm done with the phone, I go back to my cell. I do two hundred push-ups and four hundred sit-ups. When I am done with the push-ups and sit-ups, I walk to the shower. Most of the Prisoners shower in the morning, so I am usually alone. I turn on the heat from multiple faucets. I sit down on the floor. The water hits me from multiple directions it hits my chest, my back, the top of my head. It hits my arms, my legs. It burns and it hurts and I sit and I take the burn and I take the hurt. Not because I like it, because I don't. I sit and I take the pain and I ignore the pain and I forget the pain because I know that pain and suffering are different things. Pain is the feeling. Suffering is the effect that pain inflicts. If one can endure pain, one can live without suffering. If one can learn to withstand pain, one can withstand anything. If one can learn to control pain, one can learn to control oneself. I have lived a life full with suffering. I have lived a life without control. I have spent twenty-three years destroying myself and everything and everyone around me. I don't want to live that way anymore. I take the pain so that I will never suffer. I take the pain to experience control. I take the pain.

I finish my shower and I go back to my cell. I sit down on the floor and I pick up a book. It is a small book a Chinese book. It is a short book and a simple book. It is a book called Tao Te Ching, written by a man named Lao Tsu. It is not known when it was written or under what conditions, nothing is known about the writer except his name. Roughly translated, the title means The Book of the Way. I open the book at random. I read whatever is in front of me. I read slowly and deliberately. There are eighty-one poems in the book. Eighty-one simple poems. They are about life and The Way of life. They say things like in thinking keep to simple, in conflict be fair, don't compare or compete, simply be yourself. They say act without doing, work without effort, think of the large as small and the many as few. They say confront the difficult while it is easy, accomplish the great one step at a time. They say let things come and let things go and live without possession and live without expectation. These poems do not need, depend, create or define. They do not see beauty or ugliness or good or bad. They do not preach or implore, they do not tell me that I'm wrong or that I'm right. They say live and let live, do not judge, take life as it comes and deal with it, everything will be okay.

The lights go out at Ten o'clock. I stand and I brush my teeth and I drink a glass of water. I lie down on the concrete bed and I stare at the ceiling. There is noise for about thirty minutes. Prisoners talk to each other, yell at each other, pray, curse themselves, curse their families, curse god. Prisoners cry. I stare at the ceiling. I wait for silence and the deep night. I wait for long hours of darkness and solitude and the simple sound of my own breath. I wait until it is quiet enough so that I can hear myself breathe. It is a beautiful sound.

I do not sleep easily. Years of drug and alcohol abuse have sabotaged my body's ability to shut itself it down. If I do sleep, I have dreams. I dream about drinking and smoking. I dream about strong, cheap wine and crack. The dreams are real, or as real as dreams can be. They are perverted visions of my former life. Alleys filled with bums drinking and fighting and vomiting I am among them. Crackheads in broken houses on their knees pulling on pipes with sunken cheeks screaming for more I among them. Tubes of glue and cans of gas and bags filled with paint I am surrounded stumbling and huffing and inhaling as much as I can as much as I can. In some of the dreams I have guns and I'm playing with the guns and I am debating whether I am going to shoot myself. I always decide that I am. In some of the dreams I am being chased by people who want to kill me. I never know who they are all I know is that they want to kill me. They always do. In some of the dreams I keep drinking and smoking until I am so drunk and so high so goddamn fucked-up that my body just stops. I know that it is stopping and I know that I am dying I don't care. I reach for the pipe and I reach for the bottle. My body is shutting down rather than suffer the continued consequences of my actions. I don't care.

When I don't sleep, I lie on my bed and I close my eyes. I think about Lilly. I think about where she is and what she's doing. One of the requirements for her residency at the halfway house is that she have a job. She works the nightshift doing laundry at the hospital where her Grandmother is dying. She washes dirty sheets and dirty towels, used gowns and stained scrubs. On her breaks, she goes to her Grandmother's room. Her Grandmother has bone cancer, and it has spread throughout her entire body. She can't move without pain and she hasn't left her bed in two months. Her doctor has said that she will be lucky to live for another month. She's on a morphine drip and she's incoherent and she doesn't know Lilly's name anymore and she doesn't remember anything about her life. Her mind has been consumed by her cancer as much as her body has been consumed by her cancer. It has overwhelmed her and there is nothing left. Just a shell of pain and morphine. Just a shell of what was once a life.

Lilly sits by her side and holds her hand and talks to her. It doesn't matter that she doesn't understand anything, Lilly sits and holds her hand and talks with her anyway. She tells her about the halfway house she hopes that it's working she can't wait to get out. She tells her about the job it isn't so bad she's certainly done worse. She tells her about me she misses me and she wishes I were there she hopes I still love her. She tells her about the hope for a future with me and without drugs and with a sense of freedom and a sense of security. She tells her Grandmother about her fears. About loneliness she's been alone forever she doesn't want to be alone anymore. About a return to her old life she would rather die than sleep with men for money. About me she's scared that we won't survive in the World away from Institutions she's scared I'm going to leave her like everyone else in her life has always left her. About what life will be like when her Grandmother dies. She's scared because her Grandmother is the only person Lilly trusts and the only person that she is secure with and she can't imagine living without her. Sometimes Lilly can't talk anymore and she sits with her Grandmother and she holds her hand and she cries. She's scared and she can't imagine living without her. She cries.

I am leaving here in three days. I will have served my time paid my debt to society. As l lie here in bed listening to the sound of my own breathing as I lie here fighting off dreams and drifting through the deepest night, I think about what I am going to do when the steel-door slams shut behind me. I am going to Chicago. I am going to Lilly. I love her and I want to be with her. I want to be with her now and tomorrow and every day for the rest of my life. I want to sit with her, talk to her, look at her, listen to her voice, laugh with her, cry with her. I want to walk with her and hold her hand and put my arms around her and have her put her arms around me. I want to support her and have her support me. I want to stay away from drugs I can't go back and I want to help her stay away from drugs she can't go back. I want to forget about drinking and crime. I want to be a good, strong, sober man so that I can build a life. I want to build a life for me and build a life for her, a life for us together. I want to give her a Home, a place where she feels secure and free. That is what she seeks, she seeks freedom. From her past from her addictions from herself. From her loneliness. I will do anything to give it to her.

I love Lilly. I love her blue eyes and her black hair and her pale skin. I love her damaged heart. I love what lives inside of her a spirit a soul a consciousness whatever it is I love it. I want to live with it for the rest of my life. I will do anything.

I get out of here in three days.

Three more fucking days.

I lie in bed and I wait.

In the deep night.


"As smart as it is heartfelt, this tribute to friendship is a far sunnier book than Frey's debut.... Frey's cool, shrewd eye for detail ties it all together, whether he's describing the inside of a jail, a Super Bowl party, or the plaintive rootlessness of life in Los Angeles." —Malcolm Jones, Newsweek

"he engrossing story of a bizarre friendship between the author and a dangerous mobster." —People

"Frey's appeal lies in his ability to tell his down and dirty, hair-raising story in sparse, hypnotic prose--in this sense he's already a master stylist, of kind. No subject , no height or depth of human experience is too extreme for him to come around on with deadeye grace and force of his beautiful, sad, potent, irresistible prose." —Elle

"Has a ferocity and a narrative drive that won't surprise Frey's fans, but is full of unexpected heart that might." —Details

“Suffused with anger and regret, written by a man who has straddled the line between life and death and has taken his time figuring out which side he wants to jump to. He spares no gory details.” —Poets & Writers Magazine (cover story)

"Brave and bold... This is not a document but a rendering, just as Van Gogh's self-portrait distorts his face to capture the riot of emotions behind the eyes... Frey describes how he put feelings back into his life, and the effect is vivid, splashy, mesmerizing. Indeed, he has put the Technicolor back into the memoir." —Atlanta Journal-Constitution

“Examines [Frey’s] relationship with the title figure, a Las Vegas mobster who helps him through rehab, jail and the terrifying terrain of sobriety…a tender story of male friendship.” —Chicago Tribune

“My Friend Leonard is just as compelling as the first book, with the same electrifying narrative energy, stylistic daring and atmosphere of emotional risk…Frey is exceptionally good at conveying the emotional truths behind the events he relates. His portrait of his friendship with Leonard is deeply resonant and offers a fuller human portrait of a gangster than you’re likely to find anywhere else.” —Bookpage

“[A] great story by a talented writer.” —Wisconsin State Journal

“[A] must-read.” —Sacramento Bee


What makes the book as difficult and challenging as its predecessor is Frey’s ability to meet his new losses head-on. What makes it more inspiring is his determination to see things through, without the drugs as a crutch, to their unfortunate, heartbreaking end...Frey succeeds in making Leonard cut fast and close to the core." —Time Out New York

"Frey achieves another stylistic coup... Frey's style throughout is loose, untraditional, but perfectly crafted... This book packs a full emotional wallop... Frey's extraordinary relationship with Leonard is alive, a flesh-and-blood bond." —Publishers Weekly (starred review)

“A fine, grim tale full of smarting immediacy… A small fortune could be made by bottling this story and selling it as an antidote to self-pity. Frey will have to settle for the small fortune it will make in big sales.” —Kirkus (starred review)

“A raw, often visceral, reading experience. With Frey’s emotions so close to the surface, it’s impossible not to care about Frey’s struggles to reintegrate into society and prosper. Another powerful read from a talented, dynamic author.” —Booklist (starred, boxed review)

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