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Wiseguy | Study Guide

Nicholas Pileggi

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Wiseguy | Introduction | Summary



In May 1980, a man named Henry Hill joins the Federal Witness Protection Program. He faces a life sentence in jail for a massive narcotics conspiracy, and federal prosecutors, the New York City police, the Justice Department, the Organized Crime Force, Treasury agents, and the Brooklyn district attorney question him. The alleged crimes range from airline robbery heists to murder. Although his arrest does not make major headlines, officials consider it a prize because of Hill's lifelong connections to the Mafia. If officials can get him to talk, Hill can give them information that could lead to other indictments and convictions. Hill also learns while in jail his former partners, friends, and family are turning on him—one even plots his murder.

Hill's decision to become a part of the Federal Witness Protection Program means he—along with his wife and children—cease to exist. He and his family are all given new identities. On paper the switch is easy: he has never paid taxes or voted or made a major purchase in his own name. The author tells of how he is approached a year after Hill's arrest by his attorney to write Hill's story. Pileggi has been writing about organized-crime figures for years as a journalist, and he agrees to meet with Hill. Pileggi's decision to help him tell his story comes from a desire to provide "an insider's look" at a world that is rarely depicted accurately.


Pileggi begins his story of Henry Hill with a provocative sentence: "On Tuesday, May 22, 1980, a man named Henry Hill did what seemed to him the only sensible thing to do: he decided to cease to exist." What follows is a litany of the charges that were brought against Hill, from robbery to murder, by agencies from the Justice Department to the New York City police. Pileggi notes while there are many such "wiseguys" out there in the organized crime sector of the Mafia, "Henry Hill was a prize beyond measure ... He was only a mechanic, but he knew everything. He knew how it worked. He knew who oiled the machinery. He knew, literally, where the bodies were buried." This distinction is why Pileggi agreed to tell Hill's story: Hill is not like the other wiseguys. Pileggi is also surprised by Hill because he "doesn't look or act like most of the street hoods I had come across," which intrigues him. For Pileggi Hill is a literary prize in the same way he is a crime prize for the police—his story is different and will be interesting and unusual to tell. It's a rare insight into the inner workings of the Mafia that have never been told before, and it's the closest any writer has ever gotten to tell its story.

As the author of what amounts to a biography of Henry Hill, as well as an exposé on life in the Mafia, Pileggi is careful to specify he isn't planning to tell Hill's story in order to glorify him or organized crime. Even though Hill's life is sensational and his alleged crimes are the stuff of movies, Pileggi is at heart a journalist and communicates to the reader his priority is to get the facts straight and to offer a rare glimpse into this highly secretive world of the Mafia, which has been glorified as entertainment in films and television. The reader is also introduced to the term wiseguy, which is what Hill and his friends refer to each other as. Pileggi hopes because Hill is "an articulate hoodlum from organized crime," he can offer a kind of anthropological insight to Mafia culture. By laying this out in the introduction, Pileggi is establishing trust with the reader he will tell as fair, accurate, and insightful a story as possible.

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