Monk Eastman Psychopathic New York Gangster and War Hero

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Monk Eastman was a legendary New York gangster who grew up in Williamsburg. he has been called ” The  First real New York gangster.” He is also considered to be one of the last real 19th-century New York street gangsters who preceded the rise of Arnold Rothstein and more sophisticated organized criminal enterprises.

Eastman  was born  in 1875 in the tough Corlear’s Hook section of lower Manhattan to Samuel Eastman, a Civil War veteran and wallpaper-hanger, and his wife Mary Parks. His father left the family when Eastman was only five and the family had to move in with relatives.  Although he was born in Manhattan, he grew up in Williamsburg.  in 1887  his mother moved the family to 93 South Third Street. His background remains something of a mystery. Although he associated with many Jewish gangsters, there is no proof that he was Jewish.  He used a number of irish aliases, but there is no proof either that he was Irish.

Eastman’s uncle was a wealthy man and Monk could have had his  education paid for, but Monk  loved the gang life of New York and some have called him the ” By the time he was a teenager he had exasperated his god-fearing mother with his brawling, robberies and other anti-social acts. Although he stood only five feet six inches tall, he was a fearsome force. He had an instinctive aptitude for street fighting. Monk was a hard punching, club swinging, ear biting eye gouging lunatic who could pummel anyone mad enough to fight him.

When Monk was seventeen his wealthy  set the young Eastman up in a pet shop on Penn Street, which  was a useful front for Eastman’s life passion: crime.  Young Eastman first  made money from stealing pigeons and then selling them in his store.  Eastman could be ruthless and cruel to humans, but he loved animals.  He was usually seen strolling about with a huge blue pigeon on his shoulder and a couple of cats tucked under his massive arms. Anyone he found being cruel to animals got a severe drubbing. “I like de kits and boids,” Monk said. He would then proceed to beat the animal abuser to a pulp.

The moniker of “Monk,” short for monkey, was given to him by enemies who claimed (accurately) that he looked like an ape. Luc Sante describes Eastman’s looks  in his amazing book “Low Life.”  Sante writes,” Unlike his fellow gangsters of the time, Eastman was so crude in appearance that he could model for the stereotypical crook who has continued to show up in cartoons down to the present day (he had a bullet-shaped head, a broken nose, cauliflower ears, prominently throbbing veins, numerous knife scars, pendulous jowls, and a bull neck and  was usually seen wearing an undershirt, with a small derby perched on the back of his head of longish, unkempt hair.” In his book ” The Gangs of New York” Herbert Asbury writes,” Eastman distinguished himself as a colorful character in those early days by  wearing a derby two sizes two small, sporting numerous gold-capped teeth and often parading around shirtless or in torn clothing, but always accompanied by his pigeons.”

By 1892 he left Williamsburg for good and settled in the Lower East Side. He would become the terror of the area.  In the 1890′s, the Lower East Side was a warren of disease-ridden  tenements for the immigrated poor and, by all accounts, its streets were a breeding ground for pickpockets, thugs, and crooks  of all stripes. The economic Panic of 1893 only drove more people into poverty and crime.  It was a place where a sociopath like Eastman would thrive.  Eastman gained  a reputation as a neighborhood tough and eventually recruited his own gang: the Eastmans. The gang members were almost exclusively Jewish and from that arose the myth that Eastman was Jewish.

The Eastman gang  established a headquarters on Chrystie Street, and quickly became embroiled in  all out wars for territory with rival gangs. The Eastmans engaged  in  a range of criminal activity  from protection rackets, to organizing prostitution rings, to fixing elections that ensured “political” protection from Tammany Hall.

As he grew more powerful, he also started keeping pigeons, five hundred of them, by several estimates, as well as more than a hundred cats. He opened another pet shop on Broome Street, which doubled as a front for his less-lawful activities. Other gangs that answered to him during that time were the McCarthys, the Cherry Street Gang, the Fourteenth Street Gang, the Lolly Meyers, the Red Onions, and the Yakey Yakes

He quickly earned notoriety  for being a brawler. Eastman’s reputation as a lunatic  earned him the job of “sheriff,” or bouncer, at the New Irving Hall, a celebrated club on Broome Street, not far from his pet shop. According to urban legend, Eastman patrolled the New Irving with a four-foot “locust,” or police day-stick, in hand, on which he carved a notch for every head bashed. On the night he reached 49 notches, Eastman reportedly whacked an innocent bystander so as to make it an even 50. The New Irving attracted the creme de la creme of New York’s scum.  Almost all  the customers were either thieves or prostitutes.  Monk was quite skilled at using brass knuckles to knock out unruly customers, but it was his proud boast that he took them off every time he had to quiet an obstreporus female. He would only hit her hard enough to give her a black eye, but never with a weapon. Early in his career, he inflicted so many injuries that ambulance drivers dubbed Bellevue’s accident ward” The Eastman Pavilion.”

These talents were noticed by Tammany Hall, and soon Monk and his gang of Jewish toughs were Election Day fixtures, voting for their candidates two, three, four or more times and suggesting to other voters that perhaps it would be healthy for them to vote the same way. Such a valuable man as Monk made many  powerful friends, and he was routinely released just as soon as he was arrested. This left him free to attend to the business of his hood-for-hire operation, which efficiently offered head whackings or ear chewings for $15, stabbings for $25 and more serious forms of mayhem for $100.

Crime in the Lower East Side  at the turn of the 20th century was divvied up among a number  of street gangs, all competing for turf.  Most powerful of these gangs was  the Five Points Gang, a mob of mostly Irish criminals  headed by another psychopath named Paul Kelly. Eastman considered  Kelly his arch-enemy, and their enmity broke out into open mob warfare. The battles between the Five Pointers and the Eastmans raged in the streets of New York, reminding many residents of the fierce gang battles of a generation earlier. The enmity led to a huge and frightening street battle when  in the summer of 1903, the  Battle of Rivington St. was too much even for Tammany. Three men died as 100 gangsters, “in true Western style,” the New York Herald reported, “fought through 2 miles of streets for five hours in defiance of the police until a square mile of territory was panic-stricken.”

Tammany realized that the feud between Eastman and Kelly was damaging its reputation. So to avoid more bloodshed, Tammany Hall arranged a boxing match to settle the score between Eastman and Kelly. The two squared  off in a ring inside an old barn in the Bronx. It was a bruising bout, lasting two hours, and it ended in  a draw.

Eastman’s reign as a leader in the gang wars of New York City came to an end on February 3, 1904, when he was arrested for trying  to mug a young man in Times Square. The man’s family had hired Pinkerton agents to follow him and keep him out of trouble, and the guards stopped the robbery. He shot at policemen who attempted to arrest him, which earned him a ten-year sentence in Sing-Sing Penitentiary, but served only five.

When Eastman  got out of prison  many of the members of his gang were dead or imprisoned. He became addicted to drugs and he was in and out of prison. In  1917 America  entered World War I.  Eastman was now forty-two years old and he  shocked everyone by turning up at the National Guard Armory to enlist. His body amazed the doctors.

Razor, knife and bullet scars began at his ankles, ran up to his barrel chest and crisscrossed his neck and face. Decorating his belly were souvenirs of two slugs that had ripped through him years earlier, leaving wounds he had plugged with his fingers while dragging himself to the hospital. His nose had been mashed. On each side of his head, where most people have ears, dangled two shreds of flesh. What battles had this man been in? the doctors wondered.

“Oh, just a lot of little private wars around New York,” Eastman said.

Not surprisingly he proved to be a terrific soldier.   He became a doughboy, fighting in the fields of France with the 106th Infantry of the 27th Division, “O’Ryan’s Roughnecks.” Eastman was fearless in battle. There, in the trenches Monk was transformed. The hoodlum became a hero.

There were dozens of stories of his valor. Here was Monk, galloping across wasteland to rescue a wounded comrade. Here was Monk, leaping from crater to crater to wipe out nests of machine-gunners. Here was Monk, badly wounded, insisting upon leaving his hospital bed to rejoin his unit.

When he came home in April 1919, the men he had served with rallied behind him. The newspapers told of his redemption, holding him out as proof that even the most wretched can be saved. MONK EASTMAN WINS NEW SOUL, trumpeted the Tribune. OFFICERS AND HUNDREDS OF SOLDIERS WHO FOUGHT WITH HIM ASK GOVERNOR TO MAKE HIM CITIZEN AGAIN.

However, when the war ended he returned to crime. On December 26, 1920, Eastman got into an argument at a cafe with a crooked Prohibition agent over dirty money. When the agent left, Eastman followed him and called him a rat. The agent, who said he felt threatened, drew his pistol and shot Eastman dead. The agent later served three years in prison for the murder. The papers called Monk a dead thug, but Monk’s comrades  from the 106th would hear none of this. Hank Miller and John Boland, two men who had fought alongside Monk, put up funds for a military burial. “Mr. Edward Eastman did more for America than Presidents and generals,” Boland announced. “The public does not reward its heroes. Now they are calling Mr. Eastman a gangster instead of praising him as one of those who saved America. But we’ll do the right thing by this soldier and give him the funeral he deserves.”

On an overcast, freezing morning three days before New Year’s, 4,000 mourners — soldiers, women, children, blubbering old gangsters — showed up to send Monk off. Monk was dressed in full military regalia, wearing his service stripes and American Legion pin. On his shining black coffin was a silver plate inscribed Our Lost Pal. Gone But Not Forgotten.


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