Wiseguy | Study Guide

Nicholas Pileggi

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Course Hero. "Wiseguy Study Guide." Course Hero. 23 June 2017. Web. 14 Nov. 2018. <https://www.coursehero.com/lit/Wiseguy/>.

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Course Hero. "Wiseguy Study Guide." June 23, 2017. Accessed November 14, 2018. https://www.coursehero.com/lit/Wiseguy/.


Course Hero, "Wiseguy Study Guide," June 23, 2017, accessed November 14, 2018, https://www.coursehero.com/lit/Wiseguy/.

Wiseguy | Chapter 14 | Summary



For the next two years, Karen visits Hill in prison once a week, but by his third year the visits dwindle to one a month. Money has become a problem: Karen has to go back to work part-time as a dental technician and dog groomer, because the money Hill's friends owe him never gets paid. Their daughters understand Hill is in prison, but they don't know the details behind it. Even when they are older, they don't see their father or his friends as gangsters. They do understand he gambles, and gambling is against the law. They also know there are things in their home that have been stolen, but everybody they know lives the same way. Karen is grateful at least they haven't been raised to cheer for robbers in movies and television.

Karen brings contraband items into the prison for Hill to sell, such as razor blades and cigarettes and soon graduates to smuggling in pot and cocaine. Since most of the visiting-room guards are on the wiseguys' payroll, she never gets caught. Once Hill gets the job on the prison farm, she is able to bring duffel bags of items. Initially, Hill is angry with Karen for complaining about money, and that she doesn't understand when a wiseguy goes to prison he doesn't make any money. He has to learn how to make money again from the inside. Even when he begins making great amounts of money from his contraband business, a large portion of it goes to paying off guards and prison officials. He has few complaints about how he is treated by them but can't escape the fact he is in prison for another two and a half years. But after G. Gordon Liddy, the jailed Watergate conspirator, organizes a food strike at Allenwood, a minimum-security prison down the road, he realizes he may be able to transfer there from Lewisburg. Sixty prisoners have been transferred out of Allenwood, leaving 60 empty bunks. He goes to see the secretary to his counselor and begs her to do something. She takes pity on him, and sneaks him onto the list of transfers.

Allenwood is a different world, more similar to a motel than a jail. Everyone is on the honor system between morning and afternoon check-ins, and Hill is even allowed to go downtown alone for a doctor's appointment. Visitors are allowed every day, and there is a day care center for kids. Hill volunteers to work in the kosher kitchen so he can get religious furloughs—the ability to go home for seven days every three months. Hill has a rabbi write to the Allenwood authorities asking he be permitted to leave for three-day religious instruction weekends once a month. Hill is able to arrange with the rabbi to pick him up and drive him to Atlantic City where he spends the weekends gambling with Karen and the wiseguys. Hill also joins other groups that allow furloughs, meaning he is spending less and less time in jail. People back at home see him so often they think he is out of jail already. He's finally granted early parole for being a model prisoner.


Karen's difficulty navigating the world of motherhood and the world of being married to someone in prison comes into focus in this chapter, as she attempts to give her children a life of normalcy despite the fact they must often make the arduous drive to visit Hill. The prison isn't set up for children to be there for long periods of time, and despite Hill's booming business inside prison, the money doesn't seem to trickle down to Karen, since Hill's expected quality of life is also very expensive to maintain. Pileggi points out how Karen must yet again face the reality versus the illusion of being married to a wiseguy: despite stories of families taking care of each other when a husband is in prison, Karen is forced to go back to work.

In a way this shatters some of the mythology of how close-knit these families are, and instead highlights how they're all just looking out for themselves and their own hustle. The wiseguys often emphasize their loyalty, but in reality they turn their backs on each other quickly when nobody's watching. Here, Karen deals with the consequences no one will pay back their debts while Hill is in prison, because they can get away with it. The revelation their children know their father commits crimes and there are stolen goods in their homes reveals how embedded crime is in their lives, and how far Karen has come to justify their lives; she's just thankful the kids don't cheer for robbers on the television. Pileggi is adept at letting Karen reveal slowly how much her moral compass has moved over the course of her marriage to Hill. The fact she doesn't mind being complicit in smuggling in items and drugs to prison for Hill highlights how much a part of his criminal lifestyle she has become.

Hill's transfer to Allenwood demonstrates just how much wiseguys are still able to game the system from the inside, and also how lucky he is Karen remains devoted enough to him she does everything in her power to help him move. There is of course some dramatic irony here: by all appearances to prison officials, Hill is a model prisoner, busy reforming himself and his life. Pileggi notes "Henry Hill's file read like a testimonial for the modern penological approach to rehabilitation." But in reality he has become more corrupt and criminal than he was before he entered prison and has been able to manipulate the system in such a way as to find new crimes to commit from the inside. The fact he is even able to go home for so many days out of the month because of a rabbi's influence shows Hill's increasing confidence he doesn't have much to risk or lose, and in many ways he is just as invincible as ever. He seems comfortable living on this edge of possible danger, and even delights in the fact he has put one over on prison officials—lining up with his worldview everyone who isn't hustling is fair game to become his prey.

By alternating Karen and Hill's points of view while telling the story of his incarceration, Pileggi allows them to paint a portrait of two very different lives and attitudes. Hill doesn't seem to understand Karen's concern and frustration about money and their children, since he can only focus on keeping himself afloat and comfortable in prison. Pileggi lets Hill paint himself in a flattering light regarding how much he learns while in prison and how hard he works. Yet, he never acknowledges the risks Karen takes by smuggling him in food, contraband, and drugs, despite the common fear among the other wives they will be caught and punished, which would mean being separated from their children. Karen shows herself to be as brave—or foolish—as ever when it comes to Hill. Despite their tumultuous relationship, her loyalty and devotion to him are unwavering. She applies her tenacity in her every spare moment to making Hill's life easier on the inside, while never seems to worry over her own safety and comfort on the outside.

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