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In Boston in 1933, young Jerry Florea leads a gang of ruffians, including his pals Andy Norris, Skids Radzievich and Red Flanagan, in the robbery of a marketplace store. During the holdup, rookie policeman Edward Gallagher shouts at them to halt, and when they refuse, shoots at them, injuring Jerry. By the next day, Bostonians are outraged to learn that the youth will never be able to have children, but Eddie stands by his actions, and is backed by his boss, Vincent Concannon. After a jewelry store is robbed that night, Eddie visits Jerry, who welcomes him, and is surprised when Jerry reveals the identity of the thief. Days later, Eddie acts as a character witness during Jerry's trial, and Jerry, whose father has turned his back on him, races outside to thank the policeman. There, Eddie informs Jerry that he believes in him but will still arrest him at any sign of misconduct, and reluctantly listens to Jerry's next tip-off. Years pass during which Eddie rises in the department, thanks in part to Jerry's continuing insider information. The now teenaged Jerry, however, remains a delinquent, and when Eddie notifies him that he has been charged with statutory rape, Jerry takes the rap even though he knows Andy is the actual culprit. He spends the following years in the state reformatory, while Eddie continues to rise in his department, buys a luxurious house and has a baby girl with his wife, Ellen. When Jerry's sentence ends, Eddie and Ellen pick him up and urge him to live lawfully, despite his protests that he needs money. Jerry's first act, one of revenge, is to beat up Andy, after which his friends stand up for him. He then accepts a job as an elevator operator, but runs a side business taking bets on horse races. Within months, he develops a plan to fix a race and, along with Skids and Red, falsifies race results and collects his winnings. On the way home, however, he crashes his car, and after the police discover that the parolee has a gun, he returns to jail. There, Eddie, furious with Jerry's nonchalance, shocks Jerry by slapping and repudiating him. By 1941, Jerry is eager to join the Army, and Ellen convinces Eddie to try to help him gain a pardon. Jerry is at first thrilled to see Eddie, but upon hearing that he was never naturalized after moving from Italy to America and thus cannot fight, grows convinced that Eddie is out for retribution. When Ellen visits him in jail and urges him not to be bitter, the always good-natured Eddie replies that he is only upset that he can never have children or serve his country. In 1946, Jerry is released and immediately returns to running rackets. Soon, both he and Eddie have grown powerful, and they maintain an uneasy working relationship in which Jerry tips off Eddie when it benefits him to do so. When a $300,000 robbery occurs in Eddie's neighborhood, his suspicion that Jerry is involved seems justified by Jerry's handy alibi, involving an hour spent with Father Bonelli. Eddie convinces the priest that Jerry was using him, but when they all gather in an interrogation room, Jerry announces that he wanted only to earn Father Bonelli's blessing to arrange a church wedding for him and socialite Virginia Stewart, who has three small children. Upon hearing Jerry's plea that he be allowed to begin a family, Eddie, who wants to believe him and still feels guilt about shooting him, agrees to act as Jerry's best man. After the wedding, the newly respectable Jerry closes down his rackets, opens gas stations and spends his savings acquiring a pardon for his past crimes, thus enabling him to become a naturalized citizen. He and Virginia become close friends with Eddie and Ellen, until one night when Eddie learns that the armored car company near Jerry's office has been robbed of $2,500,000. The city's six bridges are closed off to seal the thieves inside the city, and a lineup is arranged, containing Jerry, Skids and Red. Furious, Eddie verbally attacks Jerry, but is nonetheless suspected of collusion in the robbery because of his close ties to the criminal. He is court-martialed, but there convinces the jury that detectives must have relationships with felons, and after being released, visits Immigration and Naturalization Service head J. J. Walsh. Walsh confirms that, because Jerry did not reveal two of his crimes to the pardon committee, he can be deported. Soon after, however, Skids induces Andy to finally confess to the rape charge, thus clearing Jerry of one of the two crimes and allowing him to stay in America. Eddie visits Jerry and urges him to give up the stolen money, and although Jerry refuses, he is devastated by Eddie's anger and, later, by Virginia's disgust. After she leaves him, Jerry asks both his gang and Eddie to meet him in the warehouse where the money is stashed. There, he informs his men that he is returning the money, allowing them enough time to flee the police, but they assume he is cheating them and begin a shootout. Outside, Eddie and his policemen hear the gunshots and break in, killing several gang members. Jerry, dying from a gunshot wound, reveals the money's whereabouts and tells Eddie he did not want to let him down. As Jerry dies in his arms, Eddie breaks down in tears.