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Five Points Gang

The Five Pointers were New York's most powerful gang in the opening years of the 20th century, and some members rank among the more influential mobsters in American history. Alumni include infamous criminals Al Capone, Lucky Luciano, Johnny Torrio, Frankie Yale and of course, Paul Kelly.

As their name suggests, the Five Points gang operated in the Five Points District in Manhattan’s Lower East Side. Their territory included Chatham Square, the Bowery and part of Chinatown. It was an Italian-dominated group lead by bantamweight boxer Paul Kelly (real name Paulo Antonini Vaccarelli). Kelly was not the typical Manhattan thug; he was a well-spoken educated man who never swore, spoke English and Italian fluently, and also had a good knowledge of Spanish and French.

In 1901, the gang became involved in a vicious territorial dispute with a gang called the Eastmans. Lead by Edward Osterman aka "Monk Eastman", the Jewish gang reportedly had about 1200 members. Eastman survived an assassination attempt in 1901 when an unknown Five Pointer shot him twice in the stomach in Chatham Square, but the undoubted climax of the conflict was the shoot-out on Rivington Street in 1903. One of Kelly’s men was shot dead during an armed robbery at one of the Eastmans’ gambling halls. The other robbers called their boss and Kelly arrived with a small army of gunmen. The fight lasted an hour and covered about two miles of streets, ending only when the gangsters ran out of ammo. Attracted by the gunfire members of an Irish gang known as the Gophers arrived on the scene and began shooting indiscriminately at gangsters from both sides. In all, there were about 100 gangsters, and the 500 police officers who arrived on the scene only added to the mayhem. The fact that only 3 people died and 7 were injured proves the inefficiency of the untrained gunmen that terrorised New York City at the time.

After Rivington Street, politician "Big Tim" O’Sullivan ordered the gangs to end their conflict or he would cease to turn a blind eye to the vice rackets being run by the two gangs. Shortly afterwards, he forced Kelly and Eastman to publicly shake hands in the middle of the dance floor at a Democrat Party banquet. However, the border between the two gangs' territories was still unclear and after several months, a new outbreak of violence seemed imminent. But Manhattan’s Sheriff Tom Farley stepped in with an unusual suggestion. Rather than needlessly killing rival gangsters, Farley came up with the idea that the two leaders could settle their differences by fighting one-on-one. The plan was agreed upon, but Kelly and Eastman ended their brawl without a clear victor.

Only the arrest of Monk Eastman prevented a second war. On February 2 1904, Edward Osterman was convicted of assault and robbery. The imprisonment of their leader struck a severe blow to the Eastmans who were no longer strong enough to threaten the Five Points Gang. For now, the war was over, and a fresh outbreak of fighting between the two gangs would not occur for another 4 years.

In 1905, the Five Points Gang were involved in another conflict, this time with the Gophers. There was a lot of bad feeling between Paul Kelly and his former underling James "Biff" Ellison, who was now head of the Gophers. The fighting began when a group of Gophers shot up the New Brighton, Kelly’s saloon of Jones Street. As Kelly lay wounded on the floor beside the corpse of another Five Pointer named Harrington, Ellison and his men sat down and enjoyed a round of drinks before leaving the crime scene. This dispute was resolved quickly with the murder of Biff Ellison.

The war with the Eastmans briefly flared up and was finally laid to rest in 1908. Max "Kid Twist" Zwerbach and Vach "Cyclone Louie" Lewis were running the gang while Eastman served his term in prison. Zwerbach and Lewis got into a barroom brawl with a Five Pointer named Louis "The Lump" Pioggi who was forced to make his escape by jumping out a 2nd story window, breaking his ankle from the fall. Paul Kelly dealt with the incident swiftly by having Kid Twist and Cyclone Louie killed.

Throughout the years, the Five Points gang increased in size by incorporating smaller gangs into it’s ranks. Members of the Plug Uglies joined in 1900. In those days it was not unusual for gangs to have a youth division, and in 1905 Kelly took the James Street Gang on board. The James Street Gang were a group of delinquent youths lead by "Little" Johnny Torrio, and later by Frankie Yale (real name Francesco Iole). Under Kelly’s tutelage, these thugs became known as the Five Points Juniors. Both Torrio and Yale graduated to the senior gang, and in later years became two very successful bootleggers during the Prohibition.

Torrio’s direct boss was Jack Sirocco, Kelly’s chief lieutenant, a role that Torrio filled after Sirocco defected to the Eastmans. Kelly taught Torrio to set up a front as a legitimate businessman and to use his cunning before his gun. Initially, Torrio looked up to Kelly but he gradually lost faith in his boss due to the continuous gang violence that the Five Pointers were caught up in. Torrio was not the most courageous of gangsters and he felt that the fighting would result in most of the Five Pointers being killed or imprisoned. He and many ex-James Street gangsters left the Five Points Gang and set up their own organization in Brooklyn. Torrio and Kelly remained friends and business associates, but the loss did affect the power of the Five Pointers.

When one looks at how many talented criminals were Five Pointers, it is easy to see why they were so successful. As well as Kelly and Torrio, Salvatore Lucania, better known as Charlie "Lucky" Luciano was another celebrated member who joined in 1916 having completed a prison sentence for possession of opium. Luciano was one of the major players in the Castellemmarase War and is the man who receives the most credit for bringing about the National Crime Syndicate.

A youthful Frankie Yale Francesco Iole aka "Frankie Yale" was the first leader of the Five Points Juniors and went on to became the chief operator in Torrio’s Brooklyn ventures. He took over the Brooklyn rackets when Torrio went to Chicago in 1915, and he later achieved status as national chairman of the Unione Siciliana, a criminal network that had strangely enough started out as a charitable organisation.

Alphonse "Scarface" Capone was a Five Points Junior who also went to Brooklyn to work for Torrio. He stayed in Brooklyn with Yale until 1918 when he fled to Chicago to avoid a murder investigation. Al Capone later inherited Torrio’s "Chicago Outfit" and earned his reputation as the most infamous gangster in American history.

With the advent of Prohibition, the gang slowly lost power as ambitious members gradually went their separate ways. By then, Jack Sirocco was leader of the Eastmans, Torrio and Capone were in Chicago, Yale and other ex-Five Pointers were in Brooklyn and Luciano was in a gang lead by "Joe the Boss" Masseria. It is not clear how long the gang survived but by 1920, they no longer commanded the fear and respect of Manhattan’s Five Points district.


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