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Monk Eastman: Psychopathic New York Gangster and War Hero

Razor, knife and bullet scars began at his ankles, ran up to his barrel chest and crisscrossed his neck and face. Bullet holes, broken nose, and flaps for ears were battle wounds. What battles had this man been in? the doctors wondered. Eastman replied, "Oh! A lot of little wars around New York"

Hi there- Bette Hardwick here from sometime in the 1920s.

The other night, Sherilyn and I were sitting around yackin’ about World War I veterans. We were watching that Netflicks show, “Peaky Blinders”, and a lot of the characters are vets.

She asked if any of the bootleggers and racketeers in Philly are vets, and you know… I didn’t know. So I volunteered to do a bit of research.

These are my notes from one of the gangsters I came across. Not exactly from Philadelphia, but a real honest to goodness War Hero… and quite a nasty guy.

Edward “Monk” Eastman (1875 – December 26, 1920)

Eastman was a mobster who dominated street crime in New York City around the turn of the 20th century. The moniker of “Monk,” short for monkey, was given to him by enemies who claimed that he looked like an ape.

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.

Eastman was known to have had a messy head of wild hair, wore a derby two sizes too small for his head, sported numerous gold-capped teeth, and often paraded around shirtless or in tatters, always accompanied by his cherished pigeons.

I found out he really liked birds, and his first and maybe only legitimate business was owner of a pet store that sold birds.

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 was beaten to a pulp.

“I like de kits and boids,” Monk Eastman.

The Eastmans Gang

By some measures, he was the last of the old-school hoods who came before the Italian-American Mafia and truly organized crime.

In his glory, Monk had commanded an army of 1,200 of the city’s meanest thugs, a grimy bunch of safecrackers, pickpockets and general ruffians from dangerous dives with names like the Flea Bag, the Bucket of Blood and Suicide Hall.

The Eastman gang had turned the area between the Bowery and 14th St. into a no man’s land, pocked by brawls with such rivals as the Yakey Yakes, the Red Onions, and Paul Kelly’s fearsome Five Pointers.

In the 1890s, 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.

These gangs grew out of the dirt-poor Jewish, Italian and Irish immigrants who flooded into New York in the late 19th century, for whom a life of crime was often the only alternative to starvation.

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, which became one of the most powerful street gangs in New York City in its day.

In 1898, Monk Eastman was arrested and convicted under the alias William Murray (one of the many Irish aliases Eastman employed). I thought that it was interesting to see he was using an Irish alias, the same as Mickey Duffy did. (Mickey was Polish).

Eastman spent three months on Blackwell’s Island (now, Roosevelt Island) for larceny.

By this time Eastman’s gang was expanding its turf and moving into new crimes, especially prostitution. They ran a series of brothels along Allen Street, referring to themselves at the time as the Allen Street Cadets. They also dabbled in gambling, opium, and enforcement.

A New Sheriff in Town

In time, Monk’s reputation as a tough guy (despite his squat five-foot-six-inch frame) 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.

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 a rowdy 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 Hospital’s accident ward” The Eastman Pavilion.”

At the New Irving Hall and Silver Dollar Smith’s Saloon, Eastman became acquainted with Tammany Hall politicians, who would eventually put him and his cohort to work as 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
* killings and other mayhem for $100.

The Five Points Gang

Eastman’s greatest rival was Paul Kelly (Paolo Antonio Vaccarelli), immigrant leader of the Italian Five Points Gang. The Eastman’s, engaged in many street battles with the Five Pointers (from which Al Capone got his criminal start). The two were surely among the first to conduct drive-by shootings.

At first, Monk had the upper hand. He led his own men into battle, and his leadership style convinced many enemy gangsters to switch sides. But the war got out of control, even by the lax standards of Tammany Hall. Innocent civilians were being killed by gang gunfire on city streets in broad daylight.

The warfare between these two gangs reached a fever pitch on September 17, 1903, with a protracted gun battle on Rivington Street involving dozens of gangsters. If you’ve ever watched the Gangs of New York, you know the battle I’m talking about.

Eastman’s reign as a leader in the gang wars of New York City came to an end on February 3, 1904, when he tried 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.

Monk ran away shooting, but the cops caught him. His bloody wars with Kelly had burned up his goodwill with Tammany Hall, leaving him to face the consequences of his crime without protection.

He was convicted that year and sentenced to 10 years at Sing Sing state prison.
In 1909, Eastman was released after serving five years in prison. During his absence, the Eastman Gang had split into several factions. Since none of the surviving gang factions wanted Eastman as their leader, he was effectively out of power.

For several years, Eastman reverted to petty thievery. During this period, he became addicted to opium and served several short jail terms.

So, what’s a poor gangster to do?

World War I arrived just in time.

After the United States entered World War I in 1917, the 42-year-old Eastman decided to join the army. 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. Eastman replied, “Oh! A lot of little wars around New York”.

He served in France with “O’Ryan’s Roughnecks”, the 106th Infantry Regiment of the 27th Infantry Division. 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 the 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.

So it was that the Monk — citizenship restored, head high — marched on Fifth Ave. with other war heroes, cheered by the good people of New York who had once quaked at the mention of his name.

Back to the ‘Hood

After his discharge from the army, Eastman quickly returned to a life of petty crime. One of his partners was Jerry Bohan, a corrupt Prohibition agent.

On the morning of December 26, 1920, Eastman and Bohan met with other men at the Bluebird Cafe in Lower Manhattan. Around 4:00 am, they argued over dirty money, with Eastman and Bohan particularly at odds.

When Bohan left, Eastman followed him and accused him of being a rat. Feeling threatened, Bohan quickly shot Eastman several times with his pistol.

Buried as a War Hero

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.”

After 12 hours of a whisky-washed wake, the flag-draped coffin was borne on the shoulders of eight uniformed veterans to a waiting hearse at the Williamsburg Bridge Plaza.

A double line of 24 buddies formed an honor guard. A procession of six polished black cars and 20 horse-drawn carriages joined the parade to the military plot at Brooklyn’s Cypress Hills Cemetery.

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.

At graveside there was a 21-gun salute, and a bugler sounded taps as Monk’s coffin was lowered into the ground.

Eastman was buried with full military honors in Cypress Hills Cemetery in Brooklyn, New York.

1 Comment

  1. Grant McPhail says:

    Interesting stuff!

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