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.
GANGSTER, DOUGHBOY, HERO
Monk Eastman of the 27th Division
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 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.
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
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 10 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 World 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 safecracking tools, a photo of Monk Eastman draped in black.