Wiseguy | Study Guide

Nicholas Pileggi

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Course Hero. "Wiseguy Study Guide." June 23, 2017. Accessed November 16, 2018. https://www.coursehero.com/lit/Wiseguy/.


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Wiseguy | Chapter 5 | Summary



Despite Vario's advice to him, Hill has no money saved. He is continually caught between being flush with cash and in debt. His day's activities vary wildly, from sitting in a pizzeria to flying to Las Vegas. He's also happy to be an untethered bachelor, until he meets Karen on a double date with Paul Jr. Karen can't stand Hill at first, and he stands her up on their second double date. Paul Jr. drives her around to find him, and she confronts him, yelling. Hill agrees to make it up to her and takes her out to dinner. Karen is impressed he seems older than other boys she knows and seems to know everyone everywhere they go. Karen's parents don't approve of him, because he isn't Jewish.

Her neighbor across the street begins to notice her, and one night tries to put moves on her, which she resists. He pushes her out of his car, and Karen calls Hill to come get her. Hill walks over to the neighbor's house and assaults him, threatening him with a gun. Someone calls the police, and they escort Hill out of the neighborhood. Karen is flattered and excited Hill would do all of this for her. Hill, fed up their parents are against their relationship, decides he and Karen should elope. They drive down to North Carolina and get married by a justice of the peace. Karen's parents are shocked but encourage Hill and Karen to move in with them to get on their feet. Hill tells Karen's parents he will convert to Judaism, and everyone believes he is a bricklayer. After Hill converts, they have a proper wedding.


Hill's relationship to money illuminates how far apart from the "real" world he lives. Like other formative lessons he's absorbed from growing up around wiseguys, saving money and spending responsibly are not habits he is accustomed to. Everyone around him seems to either owe money or be flush with cash, sometimes within the same day, a roller coaster expected and accepted in wiseguy culture. In many ways it feeds the chase and excitement for the next bigger, better, more exhilarating scheme. Vario's advice to him to save money comes from a place of fatherly concern, as someone who is far older and more established. Vario has seen many wiseguys flame out, ending up broke or dead, and has a fondness for Hill that suggests he deeply cares about Hill's outcome in life. But, Hill thrives on the unpredictability of his life. When he meets Karen, whom the reader already knows he will marry, she seems to be the only person in Hill's life who calls him out for his cavalier behavior, and Hill's response to it suggests he might subconsciously desire someone to take that role in his life.

The initial tension and conflict between Hill, Karen, and her family demonstrates some of the similarities initially between Hill and Karen. Both seem to thrive on passion and conflict, and in each other have found someone who can provide it constantly. The conflict with Karen's parents only gives them another obstacle to bond over and pull them closer together, which cements their bond as the two of them versus everyone else.

Rather than be terrified or upset over Hill's confrontation with her neighbor, Karen is excited and flattered by his actions. This reveals her to be someone who can match Hill's volatility and tendency to take risks, and on this count they seem to be made for each other. Yet, this early volatility also hints it may not be sustainable in the long term, since there is no sense of stability upon which to build a long-term foundation. While it seems exciting to the two of them now, it paves the way for volatility and conflict for the two of them down the road. When Hill marries Karen, he seems again torn between doing what's "right" (moving in with her parents) and doing what his impulses want. This mirrors his similar decision to join the army in an attempt to straighten out, and the reader is beginning to become familiar with this pattern and how brief the periods of tranquility last before Hill gets the itch to do something to sabotage it.

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