Course Hero. "Wiseguy Study Guide." Course Hero. 23 June 2017. Web. 17 July 2018. <https://www.coursehero.com/lit/Wiseguy/>.
Course Hero. (2017, June 23). Wiseguy Study Guide. In Course Hero. Retrieved July 17, 2018, from https://www.coursehero.com/lit/Wiseguy/
(Course Hero, 2017)
Course Hero. "Wiseguy Study Guide." June 23, 2017. Accessed July 17, 2018. https://www.coursehero.com/lit/Wiseguy/.
Course Hero, "Wiseguy Study Guide," June 23, 2017, accessed July 17, 2018, https://www.coursehero.com/lit/Wiseguy/.
Karen cycles through reactions upon hearing the news of Hill's 10-year sentence: move in with her parents, commit suicide, murder Hill, or divorce him. She worries about how she will support herself and the children. But two years pass before Hill goes to prison because of various appeals his lawyers file. During that time, Hill hustles as much as he can, borrowing money from loan sharks he never intends to pay back and selling everything in his restaurant. Before he leaves, Hill tells Karen not to waste any more time on him and to go her own way. Since Hill has two years to prepare for prison, he discovers Lewisburg Federal Penitentiary is the best prison he can be sent to—its guards are corrupt enough to make his stay bearable. It also has a large population of organized-crime members, including Paul Vario. Hill pays an assignment officer $200 to get into Lewisburg. He also figures out how he can get his sentence reduced by taking advantage of special rehabilitation programs. It's possible for him to be freed on parole after serving one-third of his sentence, which would amount to a little more than three years. However, his file has been marked with "OC"—Organized Crime—and so it is unlikely the parole board will free him early.
The night before he leaves, he holds a going-away party at his new restaurant, and he parties so hard he misses his required check-in time at the prison. His friends advise him to run away. Karen finally tracks him down after Hill's bondsman threatens to revoke his bond, putting him at risk of being declared a fugitive. Hill finally agrees to head to prison and is intimidated upon arrival—he's never been inside a real prison, only smaller jails. The first person he sees is Vario with a few other wiseguys, and they all start laughing at Hill, who notices the guards grow quiet for the first time. It turns out life in prison is different for wiseguys, who are isolated from everyone else in the prison and protected. Hill enrolls in a prison-education program to get a two-year associate degree in restaurant and hotel management. When he arrives in prison, he is barely literate, but he finally learns how to read. He also takes up playing tennis and starts a booking business for gamblers.
After an intense letter-writing campaign by Karen, Hill's next job at the prison is on the farm, which lies outside the prison's walls. Life inside the prison has gotten tense because of a riot; many men refuse to leave their cells. But on the farm, the prisoners have a lot of freedom, and Hill realizes he can smuggle anything into it. He's also able to use the dairy phone to call Karen, and they arrange a secret rendezvous in the fields behind the pasture. Hill starts importing pills and marijuana to the farm, where he buries them in containers. But Hill soon gets in trouble with the remaining wiseguy boss, Johnny Dio, after Hill's stash is discovered in the priest's office. Vario has to convince Dio not to have Hill killed, and Hill convinces Vario he wasn't selling dope.
Karen's reaction to the news of Hill's sentencing shows how heavily she depends on him and their lives together yet also how conflicted she is about that life. Karen seems to know on a deeper level their lives are unsustainable, particularly now that they have children, yet she also seems unable to let go of the risk and romance of it all. Despite Hill telling her he understands if she leaves him, Karen demonstrates over and over again her loyalty and devotion to Hill by doing everything in her power to help him while he is in prison.
To the wiseguys, prison is only one more place where they have almost complete control of the rules and can dominate others. Pileggi goes to great lengths to describe how easy and corrupt life on the inside is for Hill and his friends, and also how the relationship between the guards and prisoners is similar to the relationship between the police and the wiseguys—nearly anyone can be bought with enough money or business. Like life on the outside, the wiseguys have learned how to hustle the system by taking advantage of prison college courses and programs to get their sentences reduced for good behavior. However, the fact Hill is less likely to be released early for parole because the "Organized Crime" stamp on his file shows the Feds are starting to take it more seriously.
Hill's initial reaction to arriving at the prison and the subsequent laughter and celebration by his fellow incarcerated wiseguys mirror the first time he is arrested as a youth, an event that is also celebrated. This shows how the wiseguys accept and cope with arrests and prison as a normal, expected part of life in order to make it bearable, and the fact they "run" most of the prison means they face few actual consequence for their crimes—they're able to recreate their lives on the outside to a certain degree and still make money. Even though Hill signs up for programs under the guise of shaving off some of his time, they have a positive effect on him. For example, he learns to read and run a hotel and restaurant business and becomes more physically active. It doesn't take him long, however, before he is back to committing crimes. By the time Hill is able to get a job on the prison farm, he has so many privileges he may as well be on the outside. Even from that vantage, he is able to get in trouble, and this trouble marks the first time Hill deals in drugs—an activity prohibited by Vario. Pileggi suggests even while Hill is "improving himself," he is actually sliding further into levels of crime that carry even darker consequences—this time he is nearly killed before Vario intervenes. Among some of the older generation of wiseguys drugs seem to carry a different weight than other crimes. For Hill, however, "the prison was a marketplace [for drugs]. The gates would open and it was a businessman's dream." As far as he is concerned, drugs are just another commodity that can make him even more money. In this light Henry becomes an antihero in his own story, continually working against his best interests to stay protected by those who can help him. It's clear in hindsight he's proud of what he accomplishes in prison and of the privileges that are afforded to him as a wiseguy on the inside.