Lorenzo "Shakes" Carcaterra, Tommy Marcano, Michael Sullivan, and John Reilly are childhood friends in Hell's Kitchen in the mid-1960s. The local priest, Father Robert "Bobby" Carillo, serves as a father figure to the boys and keeps an eye on them. However, they start running small errands for a local gangster, King Benny.
In the summer of 1967, they accidentally injure a man while robbing a hot dog vendor. The boys are sentenced to the Wilkinson Home for Boys in Upstate New York; Tommy, Michael, and John are sentenced to 12–18 months, while Shakes is given 6–12 months. There, the boys are physically and sexually abused by guards Sean Nokes, Henry Addison, Ralph Ferguson, and Adam Styler. The abuse changes the boys and their friendship forever.
During the boys' stay at the facility, they participate in Wilkinson's annual football game between the guards and inmates. Michael convinces Rizzo, a black inmate, that they should play as hard as they can to show the guards they can fight back. Rizzo agrees, and helps to win the game. As a result of this, all four boys are beaten and thrown into solitary confinement for several weeks, whereas Rizzo is beaten to death by the guards, and to cover up his murder, his family is told that he died of pneumonia.
By the spring of 1968, shortly before Shakes' release from Wilkinson, he insists that they should publicly report the abuse. The others refuse, with Michael asserting that anyone they told would either not believe their story or not care. The boys then decide never to speak of the abuse — even after they are all released. The night before the boys were to be released, Nokes announces that the guards have arranged them a "farewell party", which actually ended by especially brutal abuse.
Thirteen years later in 1981, John and Tommy, now career criminals; encounter by chance in a Hell's Kitchen pub Nokes, by then a private security guard. They confront him, but as he dismisses the abuse they went through, they shoot him dead in front of the bar guests. Michael, who has become an assistant district attorney, arranges to be assigned to the case; he secretly intends to botch the prosecution and expose all Wilkinson's abuse routines and its covering up. He and Shakes, now a newspaper reporter, forge a plan to free John and Tommy and revenge on their abusers. With the help of King Benny and their childhood friend Carol, a social worker, they carry out their plan using information compiled by Michael on the backgrounds of the former Wilkinson guards. They also hire Danny Snyder, an alcoholic, washed-up lawyer, to defend John and Tommy.
Michael's plan will only work if, apart of revealing Nokes' shabby reputation, he further arranges for John and Tommy a firm alibi for the time of the shooting. Ferguson, when called in court as a witness for Nokes' character, is forced to admit that he, and the other guards actually abused the boys. To clinch the case, however, they need a reliable key witness. Shakes has a long talk with no less than Father Bobby, who resists at first, but then reluctantly agrees to perjure himself. At trial, Father Bobby testifies that John and Tommy were with him at the time of the shooting, watching a New York Knicks game, which its three ticket stubs he cared to keep. John and Tommy were thus acquitted and released.
The remaining guards are also punished for their crimes: Addison, now a politician who still molests children, is killed by Little Caesar, a local drug kingpin and Rizzo's older brother; Styler, now a corrupt policeman, is arrested for taking bribes and murdering a drug dealer; and Ferguson, a social worker, loses his job and family as a result of his admission in court.
Michael, Shakes, John, Tommy, and Carol meet at a bar to celebrate. Shakes remains a newspaper reporter, living in Hell's Kitchen. Michael quits the DA's office, moves to the English countryside, becomes a carpenter and never marries. John drinks himself to death and Tommy is murdered; both die before age 30. Carol stays in the city as a social worker and has a son, whom she names after the four boys.
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