Every big city in America has dealt with its fair share of organized crime. Chicago had Al Capone, and John Dillinger; Las Vegas had Busy Siegel and Frank Rosenthal, and Boston gave us Whitey Bulger. But New York is a fabled land with some of the most notorious criminals and mobsters. Here are the top 5 most notorious gangsters from New York City.

1. Charles ‘Lucky’ Luciano is considered to be one of the most powerful Mafia bosses of all time and the father of organized crime in America. He was the boss of the modern Genovese crime family and developed the National Crime Syndicate. He created alliances between five Crime families in order to decrease the amount of bloodshed so common between the powers. He was ultimately tried and convicted for running a prostitution racket in 1936 and sentenced to thirty years in prison. But during WWII, it was agreed that he would be released to help protect the harbors of New York from German U-boats. He was finally deported and lived freely outside the U.S. He died at the age of 65 after suffering a massive heart attack.
2. Paul Kelly was one of the earliest modern mobsters in New York. He founded the Five Points Gang in New York City, recruiting younger men who became famous, including Lucky Luciano and Al Capone. He used his gang and influence to help elect politicians in Tammany Hall by committing voter fraud and voter intimidation. He was known for being cultured, appreciating fine art and dining and being fluent in multiple languages. The City’s elite often frequented his club, where his political connections (and protection) only increased.
3. Monk Eastman was Paul Kelly’s counterpart (and enemy) as they rivaled for control of the city at the turn of the century. Their rivalry culminated in an extended gun battle involving both gangs. Multiple people were injured, including innocent bystanders. Tammany Hall became tired of the two gangs feuding, and Eastman was arrested for trying to shoot at police. Tammany Hall refused to exert any influence to help him, and he served 10 years in Sing Sing. He briefly served in the military during WWI at the age of 42, but ultimately returned to his life of crime. He was murdered by his crime partner after they got into a fight over money.
4. James Coonan was born the son of an accountant for famous mobsters. His life of crime started when his father was kidnapped by Michael ‘Mickey’ Spillane who ran the Hell’s Kitchen gang. To restore his honor, Coonan bought an automatic machine gun and fired at Spillane and his gang from the roof of a tenement building. He began a war between the Irish gangs and Spillane’s army. He became friends with ‘Mickey’ Featherstone and he joined his war against Spillane. Together, they joined ranks with the Gambino organization and became an incredibly powerful mob in New York racketeering circles. Eventually, Featherstone and Coonan’s relationship soured, with Featherstone turning state’s witness against Coonan who was arrested for RICO crimes going back decades. Featherstone testified against him, leading to Coonan’s conviction and sentence for sixty years.
5. Jon Gotti became the head of the Gambino crime family. Known for his extroverted behavior and expensive taste, he was called ‘The Dapper Don.’ He was later called ‘The Teflon Don’ after he was acquitted three times for three different high-profile trials. It was later discovered that he had been involved with jury tampering and witness intimidation. However, his underboss (Sammy the Bull) turned State’s witness after he learned of recordings where Gotti implicated him in multiple murders. Gotti was ultimately convicted of five murders, racketeering, tax evasion, and extortion, among other things, in 1992. He was sentenced to life in prison and died of throat cancer in prison in 2002.