Plot
Terry Noonan (Penn) returns to New York's Hell's Kitchen after a ten year absence. He soon hooks up with childhood pal, Jackie Flannery (Oldman) who is involved in the Irish mob run by his brother, Frankie (Harris). Terry also rekindles an old flame with Jackie's sister, Kathleen (Wright). Soon, however, Terry is torn between his loyalty to his friends and his loyalties to others. He is actually working as an undercover cop in order to help the police break up the gang. However, he is under great pressure and finally reveals his true identity to Kathleen but she wants to have nothing more to do with him after being told by her brother, Frank, that he is an up and coming member in his gang and has already killed two people.
Jackie is drinking in a bar one night when three members of a rival Italian gang enter and he ends up killing all three, feeling insulted that they are on his gang's territory. Frank is summoned to a meeting by the Italian mafia boss and is instructed to kill his brother "who has become a thorn in both their sides." Frank has told Jackie to lie in wait in case the meeting goes wrong and only manages to avert a war by hugging the Italian leader outside the restaurant, in full view of his gang members.
Frank arranges for Jackie to collect $25,000 that evening, telling him that the Italians are actually supporting them and this is a reward. Jackie takes Terry along as his secret back up, and they wait at Pier 84. Frank arrives with his lieutenant and, while Terry is trying to phone his police sergeant and undercover supervisor, Nick (Turturro), whom he mistakenly told to wait at another location. Frank fatally shoots Jackie although Terry did not witness him doing this. The police finally arrive and Terry tells Nick that he is quitting as an undercover operative.
At Jackie's funeral, Terry tells Frank he was at Pier 84 and also hands Frank his badge. Frank has instructed his gang to find and kill Terry. While Kathleen is watching the St. Patrick's Day parade alone, Terry goes to the bar where Frank and his gang are drinking. In a deadly shoot out, Frank and all of his men are killed. Terry is also shot and his fate is not revealed.
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