In 1920, two Irish-American youths, Rocky Sullivan and Jerry Connolly, attempt to rob a railroad car carrying fountain pens. Jerry escapes from the police, while Rocky is caught and sentenced to reform school.
Fifteen years later, an older Rocky is arrested for armed robbery. His lawyer and co-conspirator, Jim Frazier, asks him to take the blame for the robbery and in exchange, he will keep Rocky’s share of the robbery, $100,000, equal to $2,164,539 today, safe until the day he is released. Rocky agrees, and is sentenced to three years in prison.
After serving his sentence, Rocky returns to his old neighborhood and visits Jerry, who is now a Catholic priest. Jerry advises Rocky to get a place “in the old parish”, so Rocky rents a room in a boarding house run by Laury Martin, a girl he bullied as a youth. He then pays a visit to Frazier’s casino. Frazier claims to have been unaware of Rocky’s release, but he promises to have the $100,000 ready by the end of the week, and he gives Rocky $500 spending money, equal to $10,823 today.
After leaving Frazier’s casino, Rocky has his pocket picked by a gang of young toughs: Soapy, Swing, Bim, Pasty, Crab, and Hunky. After Rocky tracks them down to his old childhood hideout and proves to them he is no sucker, the tough kids admit to an admiration of Rocky’s reputation and criminal lifestyle. After retrieving his wallet and all the money therein, Rocky invites them to dinner. While they are eating, Jerry arrives and asks the gang why they have not been playing basketball.
With Rocky’s help, he convinces them to play against another team. At the match, the kids are very disorganized and fighting with the other team. Rocky asks Jerry if he can take over as referee. He takes the boys to task and they start to follow the rules. As Jerry and Laury watch on from the sidelines, Laury expresses her concern over the potential negative influence Rocky may be having on the gang, which is echoed by Jerry.
Later, while walking home, Frazier’s hit squad makes an attempt on Rocky’s life. Rocky easily spots his tail and outwits the mobsters’s attempted hit. In retaliation, he kidnaps Frazier, raiding his house at gunpoint and stealing $2,000 and a ledger. Rocky then brazenly approaches Frazier’s business partner, Mac Keefer and requests $100,000 in trade for Frazier’s release. With no other option Mac agrees and pays Rocky but as Rocky leaves, he informs on him to the police. Rocky is arrested and sets about mocking the police for their lack of evidence, even goading them to ring his lawyer (Frazier).
Frazier approaches Mac and learns of Rocky’s arrest. He informs Mac that Rocky is in possession of the ledger. This forces Frazier to tell the police it was all a “misunderstanding”, and Rocky is released. Jerry learns of the kidnapping, and decides to go to the press to expose corruption in New York. Rocky tries unsuccessfully to stop Jerry as he knows the other mobsters won’t take kindly to what the priest is trying to do.
On the radio, Jerry denounces the corruption, as well as Rocky, Frazier and Keefer. Frazier and Keefer assure Rocky that no harm will come to Jerry, but he later overhears them renege on their earlier promise and also discovers that they plan to kill both Rocky and Jerry. To protect his friend, Rocky kills Frazier and Keefer instead and after escaping the casino, makes his way to an abandoned warehouse where he is forced to kill a police officer. A standoff ensues with other police.
Jerry arrives and informs the police that he can reason with Rocky and get him to surrender peacefully. The police reluctantly agree to let the priest go into the warehouse. Jerry sees a trapped Rocky and implores him to surrender peacefully, telling him the entire building is surrounded, but Rocky takes Jerry hostage. While trying to escape, Rocky is shot in the leg and caught. After standing trial, he is sentenced to death.
In Rocky’s last few hours before this execution, Jerry visits with his old friend. He sees the negative impact Rocky could have on the Dead End Kids. Rocky informs Jerry that he intends to die proud and ‘spitting in their eyes’. Jerry pleads with Rocky to look at the negative influence he has had on Soapy and the gang. He asks him to act like a coward and beg for mercy on his way to the death house, citing the impact it would have on the gang, potentially ruining the romantic image they have of the gangster lifestyle.
Jerry walks with Rocky as he is being led to his execution. He implores his friend one last time but is gruffly rebuffed. As they enter the execution room, Rocky stoically shakes Jerry’s hand and wishes him well before walking to the electric chair. Then out of nowhere Rocky seems to break down begging and screaming for mercy. Rocky begins whimpering like a coward and this requires the guards to subdue him and forcefully drag him to the chair. Rocky seemingly dies a coward’s death. Later, Soapy and the gang read in the newspapers of how Rocky “turned yellow” in the face of his execution and they refuse to believe it. Jerry comes in and Soapy asks if it is true that Rocky had died a coward, and Jerry affirms that it is true. The gang no longer knows what to think about Rocky, or the criminal lifestyle and Jerry then asks them to accompany him to go say a prayer for “a boy who couldn’t run as fast as I could”.
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