Gangster, Doughboy, Hero: Monk Eastman of the 27th Division

The other night — thanks to Netflix — the Lady and I watched Steve Martin, as gangster Vinnie Antonelli, turn the Witness Protection Program inside out in the hilarious comedy My Blue Heaven (hereby recommended). It reminded me that one my favorite biographical sketches we presented on our Doughboy Center website was about a New York gangster named Monk Eastman. Here's Monk's story.

By Mara Bovsun 

Monk in His Early Criminal Career

Doctors at the New York National Guard recruiting station were aghast that day in October 1917 when one volunteer in the eager crowd stripped to reveal a body that looked like it had already faced down the Germans and lost. 

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," William Delaney replied offhandedly. Scars aside, the body looked pretty sturdy, so they let him sign up. 

Thus began the soul cleansing of William Delaney, real name Edward Osterman, otherwise known as Monk Eastman, the terror of the Lower East Side. 

In his glory, Monk had commanded an army of 1,200 of the city's meanest thugs, a grimy bunch of safe crackers, 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. 

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. Monk himself, it happened, was the son of a prosperous Brooklyn deli man, and initially Papa had tried hard to steer young Edward along a righteous path, setting him up as a dealer in puppies, pigeons, and kitties. But the lad found different work for himself, dance hall bouncer, and a new name, the Monk, in honor of his simian ability to climb walls and swing through windows. 

He never abandoned his pets. 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. 

Otherwise, what he carried were clubs, blackjacks, and brass knuckles. 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 had 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. 

But, in the summer of 1903, the terrifying 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." When Monk was arrested again, in April 1904, after he fired a dozen shots at a Pinkerton detective, no Tammany lawyer showed up to help him, and off he went to Sing Sing for ten years. 

By the time he came out, most of his old gang was gone and there were no battles left for him to fight. Except for the Great War. 

At 44, he became a Doughboy, fighting in the fields of France with the 106th Infantry of the 27th Division, "O'Ryan's Roughnecks." There, in the trenches, the Monk was transformed. The hoodlum became a hero. 

The 27th Division Victory Parade in New York City
Insert: Pvt. Edward "Monk" Eastman, 106th Infantry

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. 

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. 

Two days after Christmas 1920, the headline in the Daily News was EX-CONVICT, WAR HERO, SHOT DEAD. There were five bullets in Monk Eastman. A shady Prohibition agent named Jerry Bohan, who had been drinking with Monk in an East Side dive called the Blue Bird, was quickly charged with the killing. He claimed self-defense, and there was much press speculation as to how genuine Monk's celebrated rehabilitation really was. 

But the dead man's buddies 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." 

Good-bye, Old Pal! Monk's Buddies Bid Him Adieu.
The NYPD Escort Is a Nice Touch, No?

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

A few days later, a grief-stricken crook named Edward Herberger journeyed in from Philadelphia to avenge his pal. With Bohan in jail, Herberger found no one to shoot, so he did the next best thing. He stuck up a gin mill and made off with $2,000. When Philly cops arrested him, they found, along with opium and safe cracking tools, a photo of Monk Eastman draped in black. 

This article originally appeared as part of the New York Daily News "Big Town Biography" series edited by Jay Maeder. It is reprinted here with permission. We originally presented this article at our Doughboy Center Website.