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Lorenzo "Shakes" Carcaterra, Tommy Marcano, Michael Sullivan, and John Reilly are childhood friends living in Hell's Kitchen in the 1960s. Father "Bobby" Carillo, their parish priest and a youth offender himself in the past, tries to teach them right from wrong. They still play pranks and start running small errands for local gangster King Benny.

In the summer of 1967, the four boys steal a hotdog car. They accidentally roll the cart down a set of subway stairs, severely injuring an elderly man. They are all sentenced to serve time at a juvenile detention center called Wilkinson Home for Boys in Upstate New York; Shakes is given six to 12 months, while the others are given 12 to 18 months. During their stay, they are repeatedly subjected to sexual abuse and torture by head guards Sean Nokes, Henry Addison, Ralph Ferguson and Adam Styler.

While at the facility, they participate in Wilkinson's annual football game between the guards and inmates. Michael convinces inmate Rizzo Robinson to help win the game. Humiliated, the guards move the boys to solitary confinement for weeks, where they are systematically beaten. Rizzo does not survive and his family is told that he had died of pneumonia.