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 21 | Summary



Hill's arrest turns out to be a bonanza for the assistant U.S. attorney Edward McDonald, since Hill is the kind of guy who knows something about everything: "he could have written the handbook on street-level mob operations." Edward soon arranges for the Nassau prosecutors to turn the case over to the Feds, in order to catch players higher up in the game. The night Hill is arrested, detectives serve Karen with a search warrant for their home, and she doesn't yet understand the gravity of their situation. She's optimistic they can beat the case, and Hill signals to her in court where to find the drugs he's hidden in the house, which she flushes down the toilet. Yet, she grows suspicious something is wrong when Hill begins acting strangely during their visits, and when his lawyer tells her he hasn't been able to get in to see him. One day Burke asks Karen to visit his shop to pick up some materials, but when she gets there he is acting strangely and she begins to feel something is wrong. She tells him she'll come back later and leaves. She also goes to see Vario, who tells Karen he is turning his back on Hill. He gives her $3,000, and she can see he is crying.

Hill's arrest is also the first real break in the Lufthansa robbery case in over a year, since many of the witnesses and participants have been murdered or disappeared. Hill is now one of the only survivors and is finally caught in a position where he might be persuaded to talk, since he is facing 25 years to life for his narcotics conspiracy conviction. Karen might also be brought in on the conviction, another reason for him to talk. Hill also knows he now stands to be murdered by his best friends for what is at stake. The district attorney gets information Hill is next on Burke's hit list, and Vario no longer protects him. Hill's parole officer warns him about going back on the street, but after three weeks, Hill is out on bail and disappears.

Back on the street Hill knows his chances of winding up dead are great. He hopes to get back in Vario's good graces, knowing Vario's stance on drug dealing isn't moral but because his best friend is getting locked up for a connection. Hill knows his old friends, especially Burke, consider him a liability, but he doesn't want to believe it, because he and Burke were so close. The district attorney told Hill he is safer in jail, which Hill laughs at—Burke can have him killed any time. Hill and Burke finally meet once Hill is out, and on the surface, everything seems fine, but both of them know Hill can put Burke behind bars for the rest of his life. Burke tells Hill to meet him in a few days at a bar he's never heard of, and when Hill drives by it looks like all the other bars Burke uses to murder people. Instead, Hill shows up at Burke's shop two days early, where Burke asks him to fly to Florida and kill Robert Germaine's son, who was the informant. Hill is taken aback, but agrees. He also realizes Burke has assigned to accompany him the two crew members who were caught on tape discussing Hill's murder, and Hill knows if he goes he won't make it back. When Hill returns home, he is arrested again as a witness for the Lufthansa heist.


Even upon his arrest, Hill has little indication or knowledge his capture is such a boon to law enforcement because of his unusual ties to every level of the Mafia. Pileggi observes, "Hill was about to become a prize catch, a player in a larger game, though at first he didn't know it." Here he highlights it's Hill's unusual talents and strong observational skills that will be his Achilles' heel in his downfall. He and Karen both seem naively optimistic this arrest will be like any other, that perhaps Hill will serve some time in a prison where he can make himself comfortable through bribes and dealings. Pileggi's use of Hill and Karen's recollections of this time highlight the dramatic irony of their situation—they had no idea what was coming, but the reader does, and watching them continue to navigate as though their lives will remain relatively the same is startling in light of that knowledge.

Yet through Karen's interactions with the people they once considered close friends—Burke and Vario—the reader can see it dawn on both of them their days of being protected and taken care of are gone. Karen's interaction with Burke leaves both her and the reader rattled, knowing his history and tendency to take out anyone who might cause him trouble. Burke knows Hill has now become a liability to him because of everything he knows, and Karen would be an easy target to take out. Her sense of intuition and observation mirrors Hill's here, and she knows to leave the situation as quickly as possible because something isn't right. Her interaction with Vario delivers an equally devastating blow. Not only is Vario a father figure to Hill, but Vario's place within the hierarchy of the Mafia ensured Hill's safety and protection. Pileggi highlights what a delicate house of cards these relationships form, and what extreme danger he finds himself and his family in now. Pileggi's use of the interactions with Burke and Vario sets the stage for the choice Hill and Karen will have to make in order to stay safe—joining the witness protection program. His facing of a long sentence, along with Karen's possible charges, doesn't ensure their protection inside jail, since Vario would no longer be pulling any strings with lawyers and guards. For the first time Hill is facing the real consequences of his actions without an easy way out. Yet even if he were able to avoid jail, he wouldn't be able to avoid Burke's apparent plan to kill him, and therefore there seems to be no safe place for him and his family.

Hill's loyalty and history with Burke and Vario begins to affect his clarity and decision-making, evidenced by him returning to his home after he is out on bail. He seems to naively believe he can make things right again, not able to sense the gravity of his situation and the danger he is in from all sides. Pileggi observes "Hill continued to scramble, hustle, and con for days after his arrest, but these were the last spastic jerks of a hood whose time had expired, the final reflex actions of a wiseguy who did not yet know that he was already dead." This observation shows, almost sadly, Hill doesn't know any other way to exist than the life he's lived. He seems to be in denial yet again about the consequences both legally and from inside the mob's code of conduct—they know he has been questioned and he has a lot of information he can trade to reduce his sentence. Yet, Hill's keen observational skills serve him one last time, when he realizes Burke does in fact plan to kill him to keep him quiet. Hill seems to sense the walls are closing in on him from this angle, and his subsequent arrest before he can go to Florida at Burke's behest—where he knows he'll be killed—comes as a saving grace. Now Hill realizes "if I was going to survive, I was going to have to turn on everything I knew." It's a realization that comes almost too late, and which literally costs him having to sacrifice his old life and identity in order to stay alive.

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