Download a PDF to print or study offline.

Study Guide
Cite This Study Guide

How to Cite This Study Guide

quotation mark graphic


Course Hero. "Wiseguy Study Guide." Course Hero. 23 June 2017. Web. 10 Dec. 2018. <>.

In text

(Course Hero)



Course Hero. (2017, June 23). Wiseguy Study Guide. In Course Hero. Retrieved December 10, 2018, from

In text

(Course Hero, 2017)



Course Hero. "Wiseguy Study Guide." June 23, 2017. Accessed December 10, 2018.


Course Hero, "Wiseguy Study Guide," June 23, 2017, accessed December 10, 2018,

Wiseguy | Quotes


He knew everything ... He knew, literally, where the bodies were buried.

Narrator, Introduction

Pileggi details in the introduction what intrigued both him and the FBI about Hill's role in the Mafia. Unlike other wiseguys Hill was able to gain access to nearly every level of the mob hierarchy, and his observational skills mean he contains a great deal of unprecedented knowledge and insight. This makes Hill an unusual and rare subject both as a witness and as the subject of a book on the Mafia.


He seemed invulnerable ... He exuded the sort of lethargy that sometimes accompanies absolute power.

Narrator, Chapter 1

Pileggi here describes Paul Vario, the mob boss who takes Hill under his wing in a kind of father-son relationship. This depiction of Vario reveals how he is a man Hill looks up to and whom other men respect, as well as how power is the most respected characteristic among wiseguys. Because Vario is near the top of the hierarchy, in many ways he is impervious and immune to the consequences of the crimes his crew commits. His slow-moving depiction here highlights he carries himself as someone who can't be bothered with the lesser problems and issues of the wiseguys beneath him.


The extraordinary insularity of these old-world mob-controlled sections ... unquestionably helped nurture the mob.

Narrator, Chapter 3

Pileggi goes to great lengths to portray the neighborhood and insular world Hill grows up in, and to demonstrate how the environment creates a space that allows the mob to flourish as a protective entity. Most of the people in the neighborhood are immigrants and are suspicious of outsiders. They would rather get their neighborhood protection from the mob, which understands it better than the police. In exchange people look the other way and help the mob cover up their crimes.


One of these hostess parties could have kept a soap opera going for years.

Karen Hill, Chapter 6

Karen's narration describes her initial shock upon her immersion into the mob's world as a wife of a wiseguy. Karen comes from a different background, and she is shocked to discover how many husbands of her friends are in jail, and how complicated and tragically they view their own lives. But soon, Karen herself is immersed in her own troubles created by Hill, such as his imprisonment and being left to raise their children alone.


He seemed to possess a bizarre combination of generosity and an enthusiasm for homicide.

Narrator, Chapter 7

Pileggi and Hill's depiction of Jimmy Burke paints a portrait of a man who is larger-than-life, revered, and feared. Burke isn't Italian American, but his criminal skills are so respected different mob families negotiate to share his services. He becomes a close friend to Hill, and is known as "Jimmy the Gent" for his generous tipping, but his ruthlessness when it comes to violence and murder is not only his downfall, but is nearly Hill's as well.


Whack 'em first and worry about them later.

Henry Hill, Chapter 9

Hill utters this as an excuse as to why he attacked a man he mistakenly assumed was harassing Karen. His excuse reveals his belief this was just the way he was raised in the Mafia to do things, a violent code of conduct that is expected and understood. His actions show his embedded distrust of outsiders and also how naturally violence comes to him as a way to handle his anger.


A girlfriend was the ultimate luxury purchase.

Narrator, Chapter 11

Pileggi, Hill, Karen, and Linda highlight the common role of the extra girlfriend in mob culture. Karen discovers later Friday nights are when the wiseguys take out their girlfriends, while wives are taken out on Saturday night to avoid the risk of running into other girlfriends. This is a shock to Karen, and she fights Hill on it, but for Hill acquiring Linda as a girlfriend is one more status symbol that signifies his power and role within the mob. He treats Linda like an object, disregarding her feelings for him. He likes her, but he mostly just wants to be seen with her.


The prison was a marketplace. The gates would open and it was a businessman's dream.

Henry Hill, Chapter 13

Although most people would see prison as something to fear, for Hill and the other wiseguys it is a mildly inconvenient business opportunity: they must pay a lot of money to guards and lawyers to stay afloat. But it's inside prison where Hill expands his criminal-activity skills by getting into the drug trade to earn more money.


After four years behind bars Hill had no intention of going straight.

Narrator, Chapter 15

Although Hill is released early from prison for "model behavior," and despite his many courses in rehabilitation, he appears to double down on his criminal activities. Even though he earned a lot of money in prison, much of it went to the overhead costs of paying off guards and lawyers, and the only way Hill knows how to make money fast is by committing crimes. Pileggi reveals Hill to be someone who doesn't seem to learn from his mistakes.


Knowing what's not necessary is only trouble.

Henry Hill, Chapter 16

In discussing the Lufthansa Airline heist in retrospect, Hill recalls how little he knew of some of the details despite his overall involvement. Hill has learned from his lifetime of observation knowing too much can get you in trouble, either with someone like Jimmy Burke, who might decide to murder you for what you know, or with the police who can arrest and question you. The heist is full of many moving parts and crew members, and the less each one knows about the overall details that don't concern them the better off and safer they will be.


It was between the Italians, and on that level Burke didn't belong.

Henry Hill, Chapter 17

Hill discusses how little control he and Burke have over the sanctioned murder of their friend Tommy DeSimone after DeSimone kills someone from the Gambino crime family. Even though Hill and Burke have a great deal of power and influence, this quote highlights how in certain ways that will never change: they are both still outsiders because they aren't Italian. There are certain cultural codes within the Mafia that don't allow for any exceptions to the rule.


If it'd been the wiseguys, I wouldn't have heard a thing. I would've been dead.

Henry Hill, Chapter 19

Hill's sense of relief it's the police who are surrounding him and not Burke and his crew highlights how precarious the nature of loyalty and betrayal are among the wiseguys. Despite Burke and Hill's friendship, Hill is acutely aware Burke wants him dead because of how much he knows and the fact he is being questioned by the police. It's telling Hill would rather be arrested by the police than confront one of his oldest friends and risk being murdered.


It is a multibillion-dollar business in which it is understood that everyone is ratting out everyone else.

Narrator, Chapter 20

The information relayed from the detectives assigned to Hill's drug case reveals just how many wiseguys have also become informants once they are involved in the drug business. In order to avoid hard time in prison, they exchange information about those higher up the chain. By playing this cat-and-mouse game, law enforcement hopes to nab the bigger players in the game. Hill seems naive to this fact and still seems to subscribe to the Mafia's tenets of loyalty. Little does he realize he, too, will exchange information for his freedom.


Your murderers come with smiles. They come as ... people who have cared deeply about you.

Henry Hill, Chapter 21

Hill knows the walls are closing in on him, and coming to terms with the fact one of his closest friends is planning to murder him still registers as a shock to his system. Hill has always prided himself on his loyalty, and the only time he seems to demonstrate empathy is when someone who has been loyal to him is at risk of being killed. It's a bittersweet revelation to him the person who has cared deeply about him all these years has no problem killing him, and it is for this reason Hill knows he has to turn on Burke first.


The hardest thing for me was leaving the life I was running away from.

Henry Hill, Chapter 22

It's telling even though Hill knows he would be killed if he didn't leave his old life behind, he still misses the life of risk and power he gave up. Pileggi allows Hill to demonstrate that, in a way, this love of the criminal life is intrinsic to his sense of identity. Hill doesn't seem to know who he is without the role he has played for his entire life, and he doesn't seem constitutionally prepared for a "normal" life that would require stability and quiet. Pileggi raises the question of whether Hill can, in fact, change.

Cite This Study Guide

information icon Have study documents to share about Wiseguy? Upload them to earn free Course Hero access!