Saturday, July 18, 2026

New York City: The Rise and Fall of Monk Eastman

 

Monk Eastman

The shooting happened outside the Blue Bird Restaurant at the corner of Fourteenth Street and Fourth Avenue. Sunset was still a few hours away, but that didn’t matter to the boys. They’d come over from Brooklyn to visit Bradley, a waiter at the Blue Bird.

 

Monk Eastman (aka William Delaney) and Jeremiah W. Bohan left the restaurant together at about 4 a.m. 


They talked as they walked. Monk felt Bohan out, trying to see if the rumors were true.

 

“Jerry,” said the Monk, “you have become a rat since you got that Prohibition job.” He was working for the Feds, enforcing the Volstead Act, and Monk supposedly was running booze.

 

A minute later, Monk Eastman lay dead on the ground with five bullets in his body. Two slugs struck his right forearm, and another the left forearm, just above the wrist. The fourth bullet ripped a path through his hand, and the fifth one smashed through Monk’s chest and into his heart. Bohan insisted it was self-defense—Monk was getting ready to shoot him. But the evidence was against him. Monk didn’t have a gun. They found him with his arms up as if he were trying to shield himself.


Bohan made a clean getaway. He dropped his weapon outside the entrance to the subway, took a taxi for three blocks, and then grabbed another one for the last dash to his home at 276 South Third Street. 

 

Sidney Levine, a stationmaster at the Fourteenth Street Station, heard five shots at precisely five minutes after 4 a.m. “The shots came as fast as you could clap your hands,” said Levine. He followed the killer up the kiosk stairs, where he found a nickeled .32 caliber revolver on the pavement. “The weapon was warm—almost hot. The pungent odor of the explosive was fresh.”

 

Bohan got apprehended a few days later. The judge sentenced him to Sing Sing for a minimum of three years and a maximum of ten. The funny thing was, Bohan had just been paroled from Sing Sing Prison on June 22, after serving eighteen months for manslaughter. Now he was back in the joint for the same offense with another sentence that amounted to nothing more than a slap on the wrist.

 

William Delaney, the man with the “arms and shoulders of a gorilla,” transformed himself into Monk Eastman in 1902, after he became a bouncer for the Silver Dollar resort run by the indomitable Silver Dollar Smith.

 

The next year, the bouncer turned into a thug and administered a beating here, a murder there, whatever the situation called for. 



The Brooklyn Citizen
priced out what it cost to hire a competent thug in 1923. It cost $50 to $100 to have someone killed, $25 to $50 for a good beating (where the victim ended up in the hospital), $5 to $10 for an ordinary beating (just scars), and $10 plus for a freeze-out (slashing a guy’s face with a knife).

 

The paper described the typical gangster as “about 25-years-old, often less, a neat dresser, usually sporting a striped silk shirt, with a large diamond stickpin in his tie, pale, anemic looking, short in stature, shifty-eyed, and soft handed.

 

“He isn’t brave and rarely fights with his fists. His weapon is a revolver. And he usually travels in packs.”


The Monk would have agreed with the dress code of pinstriped shirts and silk coats, but he would have strenuously objected to the cowardly part. He enjoyed toying with his victims and pummeling them with his fists.

 

Early in his career, David Lamar, the Wolf of Wall Street, engaged Monk to take down his chauffeur, James McMahon, who’d beaten him senseless for firing him. Monk trounced McMahon within an inch of his life. 


The typical New York gangster was 25, wore a pinstripe suit,
and fought with a pistol, not his fists. (picture and info from 
The Buffalo Courier. April 11, 1912)

In 1903, Monk Eastman’s gang ruled all of New York, not just the East Side. “They have a regularly employed counsel, just as a big corporation does,” explained the New York Tribune. “They set aside a certain percentage of their earnings to pay court expenses of their gang. They have a regular fence to dispose of their plunder.”

 

What the paper tried to show was that the gangs were no small-time nuisance. They were an organized menace that prayed on the city, and Monk Eastman led the city’s toughest gang.

 

Monk got arrested in February 1904 over a scuffle with a young man whose rich and over-protective father had him guarded by some Pinkerton men. The boy was counting a big wad of bills on the street in front of Sig Cohen’s saloon when the gang got the idea to grab his cash. A shootout with the Pinkertons ensued. Most of the gang got away. Monk hung back to help Christopher Wallace. The next moment both men were lying on the sidewalk after police officer John Healey knocked them on the head with his nightstick. Monk got sentenced to ten years in Sing Sing. Five years later, he was back on the street.

 

After that, the Feds picked him up for smoking and selling opium. He got an eleven-month sentence on Blackwell’s Island. Monk spent some more time in prison when he stole $1500 in silver from a house in Albany. The New York Police picked him up at Westchester and hauled him back to Albany.

 

Monk enlisted in the army in 1917, then fought in France as part of the 106th Infantry, Forty-seventh Division. At first, the military had a few concerns about his “moral turpitude” and whether he was “Godly” enough to serve in the army, but his proficiency with firearms soon convinced them he might be a good fit.


Christopher Wallace was a member of Monk Eastman's Gang.

Monk’s enlistment made quite a splash in the papers, coming just weeks after his release from the Clinton Prison, where he’d spent the last two-plus years for burglary.

 

War was nothing compared to his time on the streets of New York. Monk Eastman had been shot twelve times in gang fights and cut just as many more. Soldiering was a walk in the park compared to his previous life.

 

One story said he knocked out a particularly annoying German machine gun nest single-handedly. “Monk crawled forward on his stomach and blew them up with a Mills bomb. The hail of lead that swept over him shredded away the heavy marching order pack he carried on his back.”


Another time, when his regiment fell back, Monk volunteered to stay at the front and carry wounded men off the battlefield.

 

When he came back from the war, Monk went straight, or as straight as a former gangster could.


Fat Jones, who served in the Forty-Seventh Regiment with Monk, hired him to repair cars at fifty dollars a week. “I don’t care what they say,” exclaimed Fat, “the Monk had gone straight since he come back from France.”

 

Most recently, the Monk gave up working on cars and opened a bird shop over on Broadway in Brooklyn.


The cops weren’t so sure. They were working on another angle. They believed he’d gone back to his old ways and was busy trafficking drugs and booze, with an occasional break-in here and there thrown in for good measure.

 

That’s the thing about the East End. No one knew for sure which side you’re on—allegiances were fluid and changed from day to day like a man’s name. How could it be any different when you hung out in Bowery dives with names like—the Flea Bag, Suicide Hall, the Bucket of Blood, and Last Man’s Lunch?


Before you go ...

If you’ve ever caught yourself saying, “I remember that,” you’re in the right place.

I dig up stories about Old West lawmen, outlaws, gunfighters, robberies, murders, forgotten towns, and all the strange, fascinating pieces of history that somehow slipped through the cracks. No clickbait. No fluff. Just authentic stories and actual history.

If you enjoy what you read and would like to help keep the lights on, consider buying me a Big Gulp.

Every little bit helps pay for books, newspaper archives, research trips, and the countless hours spent tracking down stories most people forgot decades ago.

Buy Me a Big Gulp / NickVulich.com

If the Old West is your thing, you may enjoy these books...

Shot All To Hell

Shot All To Pieces

No comments:

Post a Comment