Paul Kelly & Monk Eastman

The War Between New York Gang Chiefs:

Monk Eastman and Paul Kelly

Paul Kelly, aka: Paolo Vaccarelli, was born around 1876 in Italy and later immigrated with his family to New York City. He established himself first as a professional bantam-weight boxer and then later as a gang leader.Paul was the antithesis of Monk; his style of dress was conservative and he was well-educated, soft-spoken, and did not act like a gangster. Paul was able to move easily among the different levels of society; from commissioning thugs to commit mayhem and murder to holding a dissertation on art with a socialite. His New Brighton Dance Hall was a flashy dive on Great Jones street and was frequented by the New York upper class social set. New Brighton was popular with socialites when they desired to go “slumming” and to experience the wicked, seamy side of life. The “thrill” of meeting a gangster added excitement to their lives.

kelly dance

Paul Kelly became chief of the Five Pointers and used his New Brighton resort for gang social functions and for planning raids upon the Eastman gang. The Five Pointers “earned” their money from the same sources as the Eastmans: stuss games, prostitutes, political engagements, etc. Tammany Hall employed both gangs at election time and bailed out both of the chiefs when they were arrested. The Five Pointers, with fifteen hundred members, controlled the area between Broadway and the Bowery, and Fourteenth street and City Hall Park.


Monk Eastman, aka: Joseph Morris, William Delaney, Edward Delaney, etc., was born around 1873 in Brooklyn under the name of Edward Osterman. His parents were respectable Jewish restaurateurs and set Edward up with a pet store on Penn street, near their restaurant. Edward grew bored and soon abandoned his store for the excitement of street life, gangsters, prostitutes, stuss games and all of the ilk associated with it. However, Monk (Edward) always held an extreme fondness for cats and birds and he later opened up a pet store on Broome street. Monk trained a pigeon to sit on his shoulder while he went about his street travels and sometimes carried a cat with him. This “sensitive” trait contrasted sharply with his fondness for backjacking assignments and other violent deeds. Monk boasted that he had never struck a women with his club or killed one. When a lady suffered a severe lapse in manners, he blackened her eyes.


“I only give her a little poke, just enough to put a shanty on her glimmer. But I always takes off me knucks first.”1

Around 1895, Monk moved to lower Manhattan and established himself as Sheriff of New Irving Hall. The “Sheriffs” acted as armed bouncers and were responsible for keeping order (of sorts) in the social clubs or resorts that were frequented and owned by gangsters/politicians. Monk developed a patois of clipped, slangy speech and an indifferent dress style. The artist’s rendition of Monk shows him at his best, usually only when he was before a magistrate. Monk became very popular with the hoodlums of the East Side and they began to imitate his slang and sloppy clothes. Monk’s outfit usually consisted of a derby hat several sizes too small, a blackjack tucked into his pants, open shirt, and brass knuckles adorning each hand. He carried a large club and enjoyed using it, “sending so many men to Bellevue Hospital’s accident ward that ambulance drivers referred to it as the Eastman Pavilion.”2

After a few years, Monk quit his position as Sheriff of New Irving and moved up the crime ladder towards gang leader. Monk had established his kingdom by 1900 with more than twelve hundred warriors under the Eastman banner. The Eastman headquarters was a dive on Chrystie street, near the bowery, where they stockpiled slung-shots, revolvers, blackjacks, brass knuckles, and other tools of gang warfare. Their main sources of income were derived from houses of prostitution, stuss games (a form of faro), political engagements, blackjacking services, and the operations of pickpockets, footpads, and loft burglars. Tammany Hall, the political power in New York City, frequently engaged the services of Eastman to bring in the votes at election time. In return, Tammany Hall lawyers bailed Eastman out whenever he got arrested.


Monk Eastman’s feud with Paul Kelly began over a strip of territory between Mike Salter’s dive on Pell street and the Bowery. Eastman claimed domain over the territory from Monroe to Fourteenth streets and from the Bowery to the East River. Paul Kelly and his Five Pointers believed that their kingdom included the Bowery and any spoils found in this area. Eventually, the constant feuding would cause the downfall of both Monk Eastman and Paul Kelly.

Election day! Monk and a cartload of his warriors scurry to the polling place to “persuade” voters to choose the Tammany Hall candidate. Monk encounters Frankie Morello, a Five Pointer, and attacks him with his club. Monk snarls at Frankie:

“Moll-buzzer! You sneezed a parrot from me jernt on Broome! Monk starts clubbing Frankie.

Monk clubs him one last time and shouts: “Stay away from me stuss game on Rivington! Youse want to get popped like Louie? He thought I was dead, wit a hole in me belly! Youse Five Pointers can’t off me!”

votessMonk rounds up his warriors and leaves the polls. As Monk leaves, he spies Chief of Police, Bill Devery, leaning against a police cart. Devery takes his big black cigar from his mouth and tells Monk that the Legislature just passed a law abolishing the office of Chief of Police. “I am now a Deputy Commissioner, no more power, just a desk job! You better watch out!” Monk looks at him sadly and said: “Dats tough, Big Bill”

Kid Twist (aka: Max Zweibach), Monk’s chief lieutenant, climbs into his horseless carriage parked on Chrystie street and drives to New Irving Hall resort. Kid is hoping to impress his moll, Mary O’Malley, with his newly acquired Curved-Dash Olds. Mary is the most sought after dance hostess at New Irving and has lovely blue eyes framed by a heart-shaped face with long black hair. Kid pulls up to the resort, leaps out of the Olds and saunters inside the front door, looking for Mary. He notices her by the bar and waves to get her attention. Mary comes up to Kid and greets him with a kiss. Eager to show off his olds, Kid takes her outside.

Mary hollers: “Who did ya bump off to get this lovely horseless carriage?” Kid replied with pride: “No one, Monk gave me a piece of da stuss game on Rivington. I paid six hundred and twenty-five for dis Olds.” Mary whistles in awe and said: “Take me for a ride.”

Kid and Mary drive to Rivington street to check on the Eastman’s stuss game. Kid spies some Five Pointers prowling around the Eastman jernt and he decides to park his Olds in a dark alley off Rivington. “Mary, wait in the Olds” said Kid in an excited but hushed tone. He withdraws his revolver from his armpit harness and vanishes into the darkness.

Kid sought refuge behind the pillars of the Second avenue railroad and starts to pop at the Five Pointers. He spots Frankie Morello hiding behind a pillar and calls out to him: “Youse come out! Cowardly vampire!”

Frankie takes a quick pop at Kid and misses. As Frankie moves to a new pillar, Kid aims and squeezes off his revolver. Frankie screams and falls, with a bloody wound to his chest. Kid scurrys back to Mary and tells her: “Mary, drive the Olds to Monk on Chrystie street. Tell him we have a major war going down on Rivington.” Mary, her face drained of color, quickly drives off.

Monk Eastman arrives with a detachment of around fifty thugs from his Chrystie dive and they immediately take refuge behind the railroad pillars. Eastman yells out to his warriors: “Pop the cowards! Where is Kelly?”

Paul Kelly sends out forty-five of his best warriors to Rivington. Paul secretly worries that Tammany Hall and the Police Commissioner are not going to tolerate any more gang wars, especially after two years of almost ceaseless warfare. He tells the Bottler to contact Joe Brown (aka:Joseph Castano Brown) and arrange for hiding places when the battle ends and the police come looking. “Bottler, Joe is at the Chatham Club or the Plymouth cafe!” Paul directs his warriors to the various railroad pillars and they start popping at the Eastmans.

The Eastmans and Five Pointers battled until well after midnight, sending six cops running for cover. Control was gained only after the reserves from several police stations charged down Rivington street with their revolvers blazing. Monk Eastman was among the twenty arrested and he was promptly discharged after Tammany intervened. The councils of the Wigwam (Tammany Hall) suffered from public outcry and the newspapers accounts of the gang fighting and decided to call a meeting between Eastman and Kelly.

Tom Foley, a Tammany spokesperson, brought both Eastman and Kelly together at the Palm and told them peace would prevail or both gangs would be squashed. An occasional murder or blackjacking would be overlooked but not wholesale combat. Kelly and Eastman agreed to stop the stabbing and shooting and also agreed that the strip between the Bowery and Mike’s place would be neutral territory.

Peace reigned for several months between the Eastmans and the Five Pointers until the winter of 1903. One of Eastman’s warriors, Hurst, became involved in an argument with Ford, one of Kelly’s disciples. Hurst was badly mauled and one of his ears was twisted off. Monk immediately sent word to Kelly to forfeit Ford’s life or “we’ll wipe up de earth wit youse guys.”3 Kelly demurred and both sides prepared for war. Tammany Hall intervened again and both sides decided to settle the issue of supremacy by a prize fight between Kelly and Eastman.

The gang chiefs fought for two hours in an old barn in the Bronx with neither winning. The bout was declared a draw and both sides again prepared for war to the finish. However Monk’s rule ended first, when he and Chris Wallace decided to hold up a member of a rich family. Monk was arrested and Tammany Hall ignored his appeals for aid. Monk was tried, convicted and sent to Sing Sing prison for ten years.

The Final Years

Eastman’s gang fell apart while he was in prison and Kid Twist was murdered by the Five Pointers. In June of 1909, Monk was paroled from Sing Sing and returned to the East Side, but found himself without a kingdom. He was unable to reorganize his gang and ultimately resorted to being a pickpocket and dope peddler. From 1912 to 1917 Monk was in and out of prison on various charges:opium dealing, robbery, and fighting. In 1917, at the age of 44, He enlisted in the New York National Guard under the name of William Delaney. The physician at the recruiting station was shocked to see the knife and bullet scars that covered his body and asked Monk what battles he had been in. Monk grinned and said “Oh!, a lot of little wars around New York!”4

Monk went from the battles fought on the streets of New York City to fighting the battles of World War I in the fields of France with the 106th Infantry of the 27th Division, “O’Ryan’s Roughnecks.” Monk proved to be a fearless fighter, wiping out pockets of German machine-gunners, rescuing wounded comrades, and refusing to take a break when his troop was relieved. One wounded soldier from an army unit offered Monk a big fat cigar for helping him get to a hospital. Monk asked him: “Youse get this from a Boche?” The soldier replied: “No, I was in Lieutenant Herbert Asbury’s platoon on the Vesle front. He is like you, cares about us doughboys! A guy from the Y.M.C.A. came to La Pres Farm laden with boxes of cigars and wanted ten cents for each cigar. We had no money because the platoon had not been paid in months and Asbury asked the guy to give the cigars to the soldiers and look to Heaven for payment. When the guy refused, Asbury took his cigars away and kicked him in the pants. We all got two cigars, I saved one.” Monk laughed and thanked him for the cigar and then left to rejoin his troop on the front.

Monk was discharged from the service in April of 1919 and Governor Al Smith restored his citizenship. However Monk was unable to resist the lure of dope peddling and bootlegging. He was shot and killed in front of the Blue Bird Cafe on December 26, 1920 by Jerry Bohan, a corrupt Prohibition Enforcement Agent. Monk’s army comrades put up the funds for a military burial with full honors at Brooklyn’s Cypress Hill Cemetery. Bohan was sentenced to prison for first degree manslaughter and was released in 1923.

Paul Kelly closed the New Brighton in 1905 and later moved his operations to Harlem and Brooklyn where he became a labor union organizer and fought for control of the shipping docks. Paul’s criminal operations continued and his Five Pointers provided a training camp for future mobsters. Paul died from natural causes on April 3, 1936 and was buried in the Calvery Cemetery in Brooklyn.

This material was written by Frances Carle and may not be published, broadcast, rewritten, copied or redistributed in any form without permission.

The background information came from many sources. 1,2,3,4The direct quotes used came from Herbert Asbury, “The Gangs Of New York”,1928. The story about the cigars came from Herbert Asbury’s WWI letters to his brother. All of the drawings are original and are owned by Frances Carle. The drawing of Paul Kelly was based on a photograph provided by Gregory J. Brown, grandson of Joe Brown. Gregory also provided information on the Five Pointers and their slang.