Monk Eastman, Paul Kelly, Tammany Hall and the Lower East Side By Asher Sarnoff Assitant Curator

Monk Eastman  by Asher Sarnoff  Assitant Curator (Exclusively for the Museum of the American Gangster.)




       EdwardMonk” Eastman rose from the tough streets of the Lower East Side to become one of the biggest and most powerful Gangsters in New York City in the late 1800’s. Born Edward Osterman in Williamsburg Brooklyn in 1875, he was known for his love of animals, at one time being established in a pet store by his parents. He never sold many birds there however, which were one of his favorite pets to own, especially pigeons.  He instead was rumored to use the store for other less legal pursuits.  He got his start in his criminal career by learning to be a pick pocket and thief and figured out a way to use his pigeons to lure more to his coop and became very adept at it. He was known to sometimes walk around with a kitten or with a pigeon on his shoulder. Eastman gradually worked his way up to bigger and bigger crimes.  When Brooklyn got too hot for him he crossed the river and came to Manhattan. He quickly became known as someone that liked to fight and his aptitude at it led to work in dance halls as security and crowd control. Some dance halls could hold as many as 700 people and there were often fights.  Eastman and his gang controlled the people, sometimes with harsh consequences.  He was always considered to be tough and someone you didn’t want to mess with if you didn’t have to. He was known to wear a pair of brass knuckles on both hands and wasn’t afraid to use a black jack or club on patrons who got out of line. He always maintained, if he had to hit a woman he would always “Take me knuck knucks off”.

During the last 30 years of the 19th century and well into the twentieth, Tammany Hall, that powerful political machine, was at the height of its power. To ensure their candidates got enough votes to win, especially positions in the various “Wards”, they used the gangs. They intimidated voters and sometimes beat them into voting their way. Tammany hall also used gangs like the “Five Points gang” run by Eastman’s nemesis, Paul Kelly.  Both were used by Tammany Hall to ensure that the voters voted their way. Many times they did and oftentimes Boss Tweed or later on, others were the leaders of the city and no one else.  Their political machine was so strong that if any gangsters were arrested they could often get them released with no charges filed. They got Monk Eastman off on an attempted Murder Charge in a famous case where several attempts were made to break Eastman out of jail by his loyal followers.

William “Boss” Tweed


William Boss Tweed was born April 3rd, 1823 and was first elected to the United States House of Representatives in 1853. He was later elected to the New York County Board of Supervisors in 1858. The same year, he became the “Grand Sachem” of Tammany Hall. He was later elected to the New York State Senate in 1868. He rose to the heights of political power in New York City and until his death in 1878 ruled over it with a vice like grip. Some estimates are as high as 80 million dollars that he and Tammany Hall skimmed from the New York City budget over time.

Monk Eastman came up with more and more ingenious ways of ensuring victory for the Tammany Hall Democratic candidates. He did everything from beating voters, bribing drunks with booze and using dead people’s names collected off gravestones to vote with. The art of stuffing ballot boxes was also used to pad the vote even more. His men especially liked using men with beards.  They could slowly take parts of the beard off at a local barber; leaving a moustache or “Mutton Chops”. Then again they would send the man to vote and after another trip to the barber they would return him to the voting booths once more, this time clean shaven to vote another time.

New York City was wide open to the gangsters during this period. With many police officers, including judges, lawyers and sometimes, even the Mayor himself, being under the direct control of the long reach of Tammany Hall.   Tammany Hall was willing to overlook most crimes that organized gangs committed back then, besides murder.  This was a reward for when they did a good job and to placate the gangs. This atmosphere made the Lower East Side and other areas like the ‘Tenderloin” or Midtown, ripe for the taking and organized gangs of all ethnicities quickly moved in. They quickly established territories and set up legal and illegal operations. Some of these included houses of prostitution, gambling dens, “stuss” games, opium dens, cocaine bars, legal and illegal saloons and burlesque shows. These shows often masked a prostitution ring in the back.  Some also opened dog and cock fighting rings while other criminals specialized in robberies, pick pocketing, mugging drunks and more. There was any number of legal and illegal businesses that gangs became involved in as well as charging protection money to businesses both legal and illegal.  More and more, Eastman’s gang came in conflict with Paul Kelly’s “Five Pointers” as this article shows.  This running battle with revolvers and over 100 men was one of the largest shootouts of the time.

This Newspaper article is typical of the time:

There were forces within the police department and higher up politically that tried to effect change, but they were mostly in the minority and had no power to do anything. During the late 1800’s most police tended to be Irish and many were on the take from Tammany Hall. There were not many jobs for the new immigrants who came to America and many were horribly persecuted including Jews, Irish, Asians and Italians and others. Many drifted towards a life of crime simply because there was no other way to make a living.  Some may have felt angry at a society that spurned them and gave them no opportunity.

Monk Eastman first came afoul of the law in 1898 when he was arrested for larceny and sentenced to 3 months on Blackwell Island further cementing his pedigree. Other records have him possibly being arrested as early as 1892 under an alias. He rarely if ever used his real name.  Upon his release he was known to hang out with a group of pimps, they called themselves the “Allen Street Cadets”. He was known for dressing oddly at times, wearing a derby hat several sizes too small and two gold capped teeth in the front of his mouth. He sometimes sported a wild head of hair, and he was known to sometimes walk around with no shirt on in “tatters”. He quickly realized that the poor Jews who were moving into the Lower East Side were a perfect pool from which to recruit young impressionable youth who he could use for his own purposes. He taught them to be pickpockets, thieves, pimps, lock picks and other nefarious occupations. After their training, he sent them out into the city to do their work making him rich and powerful. They even had a price list for different crimes, from just beating someone up straight to the top of the list, murder, for as little as fifty to one hundred dollars.  At the height of his power, Eastman could raise 1500 soldiers and maybe as many as 2000; with other smaller gangs who pledged allegiance to him in times of trouble such as the “Gophers”. He was reported to also dress fancily at times and had many scars on his face and body from his many fights.



(Paul Kelly, Leader,The Five Points Gang)

Eastman’s gang’s main competition was the “Five Points Gang”, an all Italian gang, run by Paul Kelly. He was born Antonio Paolo Vaccarelli in Sicily in 1876. After a short stint as a boxer, Kelly used his prize money to open several brothels. He quickly became powerful too and started his own gang. He changed his name to Kelly for his fighting career, thinking it would help him get better quality fights.   Kelly controlled eastern parts of the Sixth Ward on the Lower East Side as well as Chatham Square and the five points area near Worth and Centre Streets. The “Five Points Gang” were one of the earliest large Italian gangs in New York City and were of equal size and success as Eastman’s Gang. Paul Kelly would go on to lead an empire that would last over 20 years.  He was responsible for recruiting such notable gangsters as Lucky Luciano, Al Capone and Johnny Torrio. A brief aside, there were other Italian gangs operating in New York City during the turn of the century. The “Morello Gang was active during this time too and were eventually caught by the secret service and charged with counterfeiting. They were actively counterfeiting five dollar bills as well as coins. Other gangs existed after the turn of the century too such as the 40 Thieves, 18th street gang out in Brooklyn as well as the Navy Street Gang from Brooklyn as well. Later these two gangs along with the Morello’s would form a “Camorra” and combine their families, forming a very powerful family. This “Camorra” would soon break up and some of the Morello’s would be killed in the coming fight for power. In the run up to Prohibition, many small factions began to combine under the power of big powerful “moustachio petes” or old school sicilian Mafia bosses, like Giuseppe Masseria and Salvatore Maranzano.

(Giuseppe Morello)                                

(Ciro Terranova)


The Navy St. Gang Brooklyn NY)


The “Eastman” and “Five Points” gangs would fight for years for control of the entire Lower East Side. Their fighting threatened to derail Tammany Halls plans as public outrage grew. This association with gangs, along with evidence of the massive corruptions going on under their control; would eventually lead to the end of Tammany Hall’s iron grip over New York Politics in the 1930’s, they would rule for close to 50 years most of it unopposed.

The Lower East Side in the late 1800’s; was a mass of tenements, businesses and a lot of people living very closely packed together. In some areas people lived stacked atop one another in numbers that would make most people cringe today.  Sometimes as many as three or four families would share a small apartment together and rotate sleeping in beds. People would pay a nickel to sleep on the floor in flophouses among the urine, filth and roaches and rats. Conditions were horrible and many people died of disease, dysentery, and other diseases associated with unclean living conditions. The rich New York real estate barons would be born from these tenements that were shoddily constructed and thrown together. They reaped the bounty as they saw the masses of immigrants pouring into the Lower East Side.   They made fortunes renting these dilapidated buildings out. For over 30 years the Lower East Side festered and was considered by the well to do to be a place to avoid.  Although there were some who liked to occasionally slum it with the poorer folk and hope they would see a fist fight or a famous gang member. Families froze in the tenements in winter and boiled in the summer. Often many apartments got little if any light and many lived in almost permanent gloom. With little fresh air being able to circulate due to the buildings close proximity to each other. This also created dim alleys where pickpockets, cut throats, and men specializing in robbing drunks and others called home waiting for victims to stumble across their paths.

Prostitutes walked freely in the streets of the Lower East Side, opium dens, cocaine bars, saloons, burlesque houses that doubled as bordellos, all could be found there.  These businesses both legal and illegal were very profitable for the gangs.  There were also underground gambling dens and “Stuss” games. If a gambler didn’t bet enough he might be plied with drink to loosen him up. If that didn’t work, sometimes gamblers were drugged and robbed and left outside in the street to wake up wondering what happened to them. While other times, they might be found floating in the East River the next day.

This was a time of no fingerprints, or driver’s licenses to identify you. Gang members rarely used their real names and addresses if they were arrested. Many times all the police had to identify them was their picture that was then placed in the “Rogues Gallery”. With Tammany hall lawyers on call, many gang members got away with horrible crimes that would be unimaginable today. Rape, robberies, shootings and gunfights in the streets were common and fights happened all the time. All of these and more crimes were done routinely and rarely were any arrests made that weren’t overturned later by a friendly judge to Tammany Hall. Witnesses could be easily bought for cash who would say whatever you wanted and many politicians and cops were on the take as well. The City staggered under tyranny and graft never before seen in modern times.

Even at the height of his power, Monk Eastman still committed some crimes that he didn’t have to commit. He was known to have a bad temper and survived many fights. He was shot twice in the stomach in 1902, in Chatham Square. He calmly got up and plugged the holes with his fingers and calmly walked to the hospital.  He lived after having an operation.

Because of the massive influx of different ethnic groups throughout the last half of the 1800’s New York City’s population had quintupled in ten years at one point. Jews fleeing the pogroms all over Europe and Russia arrived in New York along with Italians and before them the Irish, who were fleeing horrible famine and poverty as well. Many of them quickly began to settle in the Lower East Side one of the city’s poorest areas. Their dreams of an America with streets paved of gold were quickly shattered when they realized they faced nothing but more persecution and suffering in a new land.

Many Jews, Irish, Italians, Asians and others were persecuted and kept out of mainstream society, a pattern that would last decades longer. Much of the time, jobs were few and far between and barely paid enough to sustain one person let alone a family. Children as young as 6 or 7 worked in factories. The 1890 Census showed that 1 million children aged 10-14 worked in America and by 1910 that number had doubled to 2 million.  Many families depended on these multiple incomes to survive. Children were also preferred by businesses because they were faster moving, easier to train and could be hired for lower wages than adults.  Many families in the Lower East Side lived in horrible conditions and didn’t have enough to eat. Some women turned to prostitution to make ends meet, while some became drug addicts or alcoholics. There were many houses of ill repute where for a price almost any sexual indulgence could be fulfilled. It was a time of decadence without much rule of law where the gangs enjoyed unrivaled power and success. Eastman and his gang prospered during the late 1890’s as his gang grew in size they were more brought under the wing of Tammany Hall. Due to persistent fighting with Kelly and the five point’s gang, Tammany Hall tried to intervene many times, throwing big parties for the gangs. Finally Kelly and Eastman decided to have a fight just between them in 1903 using Queensland rules for boxing. The men, along with a crowd, made their way by train up to the Bronx where they arrived after much cloak and dagger type movement at a farm house. The ring was drawn out and many had come up for the fight to wager on the duel. Kelly was a former boxer, but Monk the much bigger man was favored by many, he was a veteran of many street fights and bar brawls and outweighed Kelly. Both men knocked the other down and fought for four rounds. After the fourth round, both almost collapsed and couldn’t continue and the fight was declared a draw.

Towards the end of the century, gangs and Tammany Hall came under increasing pressure to reform. Monk Eastman was finally convicted and sent to jail for Larceny.  He unfortunately had tried to rob an influential man’s son on a whim on February 3rd 1903, on 42nd street and Broadway.  As the 0man stumbled out of a saloon and began to count his money, Monk and another gang member set upon him to rob him thinking him an easy mark. What they didn’t know was that the Pinkerton agency had been hired by the man’s father to watch over him during his drunken debauch through New York City. A gunfight ensued down 42nd street, where Monk and his cohort emptied their weapons at the Pinkertons and Eastman ended up throwing his empty gun at one of them breaking a store window. As Monk fled down the street a patrolman who had heard the shots and was headed to investigate, knocked him cold with his nightstick as he rounded the corner. Eastman awoke on the floor of a jail cell. He was finally convicted later and was sentenced to ten years in Sing Sing prison.

Eastman benefited from a new law that would give convicts good behavior and take time off their sentences if they didn’t start trouble. Eastman was a model prisoner in Sing Sing and was released after serving more than half his sentence. Conditions at Sing Sing were deplorable. As evidenced by this New York Times Article which quotes Arthur Conan Doyle as saying after a visit to the prison, “It is a disgrace to the state and is 100 years behind the times, it should be burned down.”

Arthur Conan Doyle on Sing Sing N.Y. Times Article

Inmates were put in a cell that measured 7’x4’ with little air or ventilation. Their toilet was a bucket which would begin to smell especially during the sweltering summer heat. Rats and roaches were commonplace and inmates froze in the winter and baked in the summer. During the day, many worked at hard labor breaking stones with sledge hammers.  Sometimes two men were thrown together in these small cells and it wasn’t uncommon for men to be put in a cell together that were known to not get along. Eastman, after his release was a changed man and the New York he remembered was beginning to change. He had little of the money and power he had five or six years before and his gang had been taken over briefly by Max “Kid Twist” Zwiefach.  Kid Twist, briefly held control but after rival factions began to fight and break away his gang finally broke apart, leaving Kelly as one of the most powerful gangsters of the city.  He would dominate gang life for many years to come.  Eastman would dabble with crime after his release being arrested in Buffalo for an attempted robbery, he was soon released, he made attempts to come back to New York City, and he purportedly opened an opium den but was hounded by police more and more.

(Max “Kid Twist”Zweifach)    

As the buildup to World War 1 started to dominate the public conscience and we finally got involved, Eastman decided to give up a life of crime and join the Army. He lied about his age and was accepted into the Army in 1917. Some say at the age of 42 but he listed his age as 39.  Upon his physical the doctor, noticing the many scars and bullet holes on his body asked what wars he had been in.  To which Monk replied “Oh a lot of little wars around New York”. The army at this time was not checking people’s criminal histories and he was accepted into the 106th infantry regiment of the 27th Infantry Division which came to be known as “Ryan’s Roughnecks”. After distinguishing himself at boot camp he was promoted quickly to Private First Class Doughboy and sent off to France to fight the Germans. After his discharge in 1919 and having distinguished himself in several battles, including the Hindenburg Line, New York Governor Al Smith restored his U.S. Citizenship.  He was never awarded any medals, some say due to so many of his superior officers being killed. The 106th took massive casualties of up to 80% killed, in the numerous battles it fought in France.  Many of his fellow soldiers and some superior officers who lived through this, told stories of some heroic things he did in battle. He saved one man’s life that was shot in the shoulder and he pulled him to safety. Years later, when Monk was murdered, he offered to pay for his funeral in full.


   Monk’s Final Years


Monk returned to a life of petty crime with a former associate named Jerry Bohan, a less than scrupulous prohibition agent who Monk had worked with in the past. He was also rumored by some to be back in the opium business again. Monk and Bohan had also had disagreements as well in the past. On December 26th, 1920 a group of men, including Eastman and Bohan met at the Bluebird café in lower Manhattan. Around 4am a disagreement arose between the group, especially between Bohan and Eastman over money.  When Bohan left, Eastman followed him and accused him of being a rat. It is possible he was threatened by Eastman due to their earlier conflicts and he quickly drew his pistol and killed Eastman on the spot with several shots. He was buried with full military honors in Cypress Hills Cemetery in Brooklyn, New York City.  Bohan was later convicted of the murder and sentenced to three years in jail.  Monk Eastman remains mostly a mystery in the police department records; he almost never used his real and had several aliases. He enlisted under his real name but the police didn’t have any record of him as Edward Eastman.  There are other accounts of his death where the assailant was not seen and some say he wasn’t killed by Bohan at all. Most people at the time didn’t want to get involved in something related to gangsters and there were no official witnesses who came forward that saw anything. Much of the death of Monk Eastman is shrouded in mystery; however he will be remembered as one of the earliest millionaires and most influential gang leaders of his day. Very few families or gangs ever reached the height of power or size that his gang reached.