Wiseguy | Study Guide

Nicholas Pileggi

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Wiseguy | Chapter 19 | Summary



On the day Hill is finally arrested, his friends and family are driving him crazy and he is doing cocaine to stay awake during his long hours at work. He's having a hard time earning money since the Lufthansa heist, since Burke is lying low. The FBI pays him a visit looking for guns, and Karen helps Hill by hiding the only one in her underwear. Hill picks up some more guns to sell, and as he's putting them in his trunk he sees a helicopter hovering over his house. As he drives to Burke's, he notices the helicopter seems to be following him, but then it disappears. When Burke sees the guns, he's irate: they're not the ones he wanted. Hill is aware at least eight of the guys who worked the Lufthansa heist are now dead, and so he is careful not to anger Burke. The helicopter continues to trail him.

Meanwhile, Hill has to deal with his girlfriend, Robin, as well as his drug courier, Judy. He warns Judy not to make any calls about the drugs and travel logistics from his house, but she ignores him. The cops are listening in, and now know when and where the drugs are going. When Hill leaves to drop Judy off at the airport, his car is surrounded by unmarked cars, and he believes he is going to be killed by Burke for his role in the Lufthansa heist. He relaxes when he realizes it is the police, who aren't going to kill him.


Karen demonstrates yet again she is devoted to keeping Hill safe and out of trouble, as evidenced by her hiding of the gun. As much as she is at times torn and conflicted about their lifestyle, she also doesn't seem to see a way out of it, which reveals her to be just as enthralled by it as Hill is. Hill, for his part, doesn't seem aware of the danger he is putting Karen in as his accomplice, and how their actions might affect their family and ability to take care of their children if both of them are arrested. On one hand, Hill's actions show he considers Karen a trusted partner, but on the other they show he has little regard for anyone beyond himself.

Pileggi shows Hill's paranoia of the looming helicopter in a way that reveals how his relationship with drugs has changed his perception. The reader knows it's possible the helicopter is following Hill, but it's equally possible his paranoia is due to his drug use, and this doubt puts the reader in the same role of attempting to separate facts from paranoia. The drugs seem to be impairing Hill's once-great judgment and observational skills, such as his neglect in ensuring Judy follows his instructions not to use his phone. In a way Vario has been proved right in his assessment that getting involved with the drug trade is a bad move for his associates—it's impairing Hill's judgment and causing him to take increasingly desperate measures to stay afloat financially. It's also telling once the police surround Hill, he is relieved it is not Burke who has come to kill him. The fact that being arrested by the police is a safer bet than meeting his old friend demonstrates just how toxic his relationship with the Mafia has become. Hill realizes at that moment "If it had been wiseguys, I wouldn't have heard a thing. I would have been dead." Getting arrested is now a safer bet for him than being confronted by his friends. This chapter marks a significant shift in the sense of trust between Hill and the men he considers to be his family and friends—he can no longer trust they have his best interests at heart. The fact he is safer in the custody of the police than in the presence of his friends and colleagues signifies something is fundamentally broken in his mob family that likely cannot be regained, and thus marks the shift into Hill's swift downfall. Up until now Hill hasn't been able to believe the worst his friends are capable of, and it's not until his unexpected relief at seeing the cops that he realizes how much of his life is at stake if he is turned back over to his former friends.

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