America’s Most Infamous Criminal Gangs

The Dead Rabbits were a feared gang of Irish immigrants who prowled the Five Points neighborhood in Lower Manhattan, so named because it was the intersection of five narrow streets. Members rumbled with the Bowery Boys in the mid-19th century – battles brought to the big screen in the Martin Scorsese film “Gangs of New York.” When they weren’t brawling, the Dead Rabbits robbed and picked pockets. It wasn’t just young men doing violence: One of the most feared Dead Rabbits was “Hell-Cat Maggie,” a woman who reportedly filed her teeth to points and wore brass fingernails.

Another Irish immigrant group of toughs were the Whyos, who were formed from the remnants of disparate Five Points gangs. They were pickpockets and petty thieves and sometimes murderers who branched out into prostitution and counterfeiting and later used their ill-gotten gains to open casinos and bars. They were very violent. They carried eye gougers and accessorized shoes with ax blades. Some kept a pricing catalog of nefarious deeds such as the cost of a punch to the face, the chewing off of an ear, and murder.

The two Irish gangs that controlled much of the criminal activity in Boston were the Charlestown Irish Mob and the Winter Hill Gang. The Charlestown Irish Mob was led by the McLaughlin brothers, while James “Buddy” McLean was in charge of the Winter Hill Gang. A gang war erupted in the 1960s in which one of the McLaughlin brothers was killed. This led to the decline of the Charlestown gang. Besides the usual criminal activities of gangs, the Winter Hill Gang also fixed horse races. The most famous leader of the Winter Hill Gang was Whitey Bulger, portrayed by Johnny Depp in the film “Black Mass.”

Italian gangster Paul Kelly combined the remaining members of the Dead Rabbits, Whyos, and other Five Points gangs to form the Five Points Gang in the 1890s. Kelly was able to pull together an army of 1,500 thugs who fought turf battles with other gangs such as the Jewish gang of Monk Eastman. When they weren’t fighting, the Five Pointers operated robbery, racketeering, and prostitution rings. They also worked as muscle for the corrupt Tammany Hall political machine. Before the gang’s influence declined in the 1910s, Kelly mentored future organized crime big shots Al Capone, “Lucky” Luciano, and Johnny Torrio.

The “Westies” were an Irish-American criminal gang that operated out of the west side of Manhattan. They used their muscle to intimidate the shipping trade before that industry declined after the 1960s. That, and gentrification of the neighborhood, led to the decline of the organization, which came under the influence of the Gambino crime family in the 1970s and 1980s. The Gambinos hired some of the gang as contract killers. The Westies had an especially violent reputation – they killed and dismembered victims. Friction between gang founder James Coonan and another member, Mickey Featherstone, developed in the 1980s. Featherstone was arrested on a murder charge. To clear his name, he taped recordings of Coonan and other Westies that led to the takedown of the gang.