The Five Points gang, founded by Paolo Antonio Vaccarelli under the Americanized name Paul Kelly, built a reputation for extreme brutality in lower Manhattan, often fighting rival gangs until one side was wiped out. While the Five Points district had deep Irish-American roots, Kelly’s organization became predominantly Italian, absorbing members from older Irish gangs like the Dead Rabbits and the Whyos as it grew. The gang drew its name from a notorious Manhattan intersection where four streets converged, an area known for slum tenements, gambling dens, and brothels by the 1840s. The district, now part of modern-day Chinatown, had been home to waves of poor English, Scottish, and Irish immigrants who faced heavy ethnic prejudice from native-born Protestant Americans.
Catholic immigrant communities formed local street gangs before the Civil War, including groups like the 40 Thieves and the Shirt Tails. Those gangs largely collapsed by the 1870s, and their remaining members joined more powerful outfits such as the Dead Rabbits and the Whyos, whose influence eventually faded as new waves of Italian and Eastern European Jewish immigrants arrived. Kelly’s Five Points gang competed with Monk Eastman’s organization, a predominantly Jewish crew that had absorbed many Irish members. The two groups clashed over rackets and territory on Manhattan’s Lower East Side, escalating into open warfare by 1903.
Eastman was shot in the stomach by a Five Points member in 1901 but survived, and one of his men killed a Five Pointer in retaliation. A gun battle involving roughly 50 Five Pointers, including Kelly and Johnny Torrio, lasted several hours, forcing police to withdraw from the scene while three men were killed and many others wounded. When police finally regained control, they arrested Eastman, but a Tammany Hall-controlled judge released him within hours after he swore his innocence. The public outrage over the street violence prompted Tammany Hall deputy Tom Foley to summon Kelly and Eastman for a meeting, warning them that continued fighting would cost both gangs political protection.
Peace held only briefly, and violence flared up again within two months. Officials then arranged a boxing match between Kelly and Eastman, with the winner’s gang claiming the disputed territory. Hundreds of men from both sides gathered in the Bronx to witness the fight. Kelly, a former boxer, was expected to dominate the early rounds, but Eastman was larger and fought fiercely.
The fight lasted two hours, leaving both men battered, but neither was knocked out, and the match was declared a draw. The leaders then told their men the war was not over. At that point, Tammany Hall officials decided to back the Five Points crew and withdrew all legal and political support from Eastman’s gang. In 1904, Eastman was beaten unconscious by a police officer who foiled a robbery in progress.
He was convicted and sentenced to ten years in Sing Sing prison. With Eastman imprisoned, the Five Points gang faced no serious rival for control of organized crime on the Lower East Side, and Kelly expanded operations into other parts of Manhattan and New Jersey. Eastman’s successor, Max “Kid Twist” Zwerbach, a former Five Pointer who had defected, was murdered in 1908, allegedly by Five Points hitmen on Kelly’s orders. Kelly took a more polished approach to his criminal operations, opening the New Brighton Athletic Club on Great Jones Street, a two-story cafe and dance hall where he charmed socialites and respectable citizens.
His educated demeanor impressed many of New York’s elite. In 1905, Kelly was shot three times by two former lieutenants, James “Biff” Ellison and Pat “Razor” Riley, during a gun battle inside the New Brighton. The failed assassination and the closing of the club under pressure from Tammany Hall and police commissioner William McAdoo marked the beginning of Kelly’s fading dominance in the underworld. After the New Brighton shut down, Kelly relocated operations to Italian immigrant communities in Harlem and Brooklyn while maintaining ties to his old neighborhood.
Using his legal birth name of Paul Vaccarelli, he served as vice president of the International Longshoremen’s Association, though he was expelled in 1919 and later reinstated. Kelly was appointed to a strike resolution commission with the support of the mayor and brought a dispute to a close without winning concessions for the strikers. He is believed to have become a labor racketeer during the 1920s, providing muscle in labor disputes. He died of natural causes in 1936.
The mafia gangs gradually absorbed the rackets once controlled by the Five Points gang. Former Five Pointers, including Torrio, Al Capone, and Charles “Lucky” Luciano, rose to leadership positions in new organized crime groups and expanded operations on a national and international scale with backing from businessman Arnold Rothstein.