Of all of the early gangsters of New York, probably the most violent, stupid, and
vicious hoodlum of them all was a Jew who called himself Monk Eastman. The moniker
of "Monk," short for monkey, was given to him by enemies who claimed (accurately)
that he looked like an ape and sometimes literally dragged his knuckles on the sidewalk
as he loped down the street in a slumping gait. Of all the mobs that have terrorized
New York City in the past two centuries, none gained the reputation for sheer psychopathic
violence as did the Eastman gang from the Bowery.
Eastman was born around 1873 in Brooklyn under the name of Edward Osterman. His parents
were 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 (a Jewish gambling game similar
to faro) and all of the ilk associated with it. However, Monk 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 under each arm. This "sensitive" trait contrasted
sharply with his fondness for blackjacking assignments and other violent deeds at
the behest of local Tammany Hall politicians, or as part of his own robberies and
To the end of his life, Monk dressed like a slob out of a garbage can and his speech
was Neanderthal Brooklynese. It is a mystery how so incredibly stupid and ignorant
a man as he was could evolve into the leader of a major New York street gang, but
he did. Monk's circus-freak appearance was not enhanced by his wardrobe. Most gangsters
were and are clothes horses and the nattiest dressers in town, viz. John Gotti, but
Eastman's outfit usually consisted of a derby hat several sizes too small, a blackjack
tucked into his pants, soup-stained vest, 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."
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," the gallant Hebrew once told a reporter.
Around 1895, Monk moved to lower Manhattan and established himself as Sheriff of
New Irving Hall, "sheriff" being a slang term for a whorehouse bouncer. Monk also
"kept order," if you want to call it that, at a number of saloons and social clubs
owned by politicians and gangsters. After a few years, Monk moved up the crime ladder
towards gang leader. Monk had established his kingdom by 1900 with more than twelve
hundred thugs, burglars, pickpockets, cutthroats and stickup men under his nominal
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 and dice games, political strongarm 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 lifelong feud with rival gangster Paul Kelly (who despite his name
was Italian, having been born Paolo Vacarelli) 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.
On election day of 1902, Monk and a cartload of his goons were scurrying to the polling
place to "persuade" voters to choose the Tammany Hall candidate, when they encountered
Frank Morello, a Five Pointer. Monk accused Morello of stealing a parrot from his
pet store, which he still maintained as a sideline, and then began beating Morello
with his famous club. After clubbing him down and leaving Morello a bleeding mess
on the sidewalk, Monk shouted at him, "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!"
Some hours later, Kid Twist (Max Zweibach), Monk's chief lieutenant, drove up to
the New Irving Hall cathouse in his new horseless carriage hoping to impress one
of the ladies of the evening there, Mary O'Malley, with his newly acquired Curved-Dash
Olds. (Jewish criminals have for some reason always preferred Irish women, which
considering the way most Jewish women look is perhaps not so surprising.) The Irish
whore was duly impressed and he took her for a ride, put-putting down Rivington Street.
He drove to one of Eastman's stuss games in a tenement, and just as he pulled up
to the curb, he saw the bloodied Morello and some of his fellow Italian gangsters
from the Five Points mob heading for the door, clearly out for vengeance and intending
to smash up the game inside and rob it. Zweibach pulled out his revolver and immediately
opened fire, killing Morello.
The fat was now in the fire. Both gangs descended in force into the area and sheltered
behind the iron columns of the railroad bridge over the intersection of Chrystie
and Rivington Streets, and started blasting away at one another with pistols and
sawed-off shotguns over a period of about six hours. The police attempted to intervene
twice but were driven away by a hail of bullets from both sides, and it wasn't until
almost midnight that the cops assembled enough men and weapons to storm down the
street in force and break up the gun battle. It is not known how many gangsters were
killed or wounded, since the thugs carried away most of their casualties for secret
burial in tenement basements and waste ground, but it is estimated that half a dozen
men on both sides died and about fifty were wounded. The casualties might have been
greater had not the iron pillars of the railroad bridge provided an excellent bullet-proof
This was the last straw for Tammany Hall and the city authorities, and ward boss
Tom Foley from Tammany dragged the two gang leaders to a truce meeting and laid down
the law: there were to be no more of these spectacular shenanigans. 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
Peace reigned for several months between the Eastmans and the Five Pointers until
the winter of 1903. One of Eastman's hoodlums named Hurst became involved in an argument
with a man named 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." 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.
(Kelly was at least thirty pounds lighter and several inches shorter than Eastman,
but had been a professional bare-knuckles boxer in his youth.) 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 one of his henchmen, Chris Wallace, decided on impulse to "roll"
or mug a well-dressed young man whom they saw reeling out of a barroom quite drunk.
They didn't know that the boy's wealthy father had assigned a couple of Pinkerton
detectives to follow and protect his wastrel son, and the Pinkerton men intervened
and succeeded in beating down and handcuffing Eastman. Monk was arrested and Tammany
Hall ignored his appeals for aid. Monk was tried, convicted and sent to Sing Sing
prison for ten years.
Eastman's gang fell apart while he was in prison, and in 1908 Kid Twist was murdered
by a Five Pointer named Louie the Lump over the affections of another Irish girl,
Carroll Terry. 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,
posing as an Irishman 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!"
He 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, in an argument over
some hijacked liquor.
Eastman's career is interesting because it gives the lie to the contention that organized
crime in this country has always been an Italian or Irish phenomenon. Eastman was
the first in a long line of vicious Jewish urban criminals who include such stellar
lights as Dopey Benny Fein, Nate "Kid Dropper" Kaplan (so-called for his penchant
for mugging newsboys and robbing them of their day's change), Jacob "Little Augie"
Orgen, Arthur "Dutch Schultz" Flegenheimer, Bugsy Siegel, Meyer Lansky, and Sidney
Korshak. Organized crime in America has always had a prominent Jewish presence and
in some cases, as in the Eastman era, it has even been predominantly Jewish.