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Monk Eastman enlisted to serve in World War One at the Bedford Atlantic Armory

Monk Eastman goes to WWI: The Bedford Atlantic Armory

Address: 1322 Bedford Avenue

Status: Homeless Shelter


* Part of this story originally appeared in an article I wrote for Military Heritage Magazine.


A hushed awe fell over the army medical inspectors when William Delaney’s clothing hit the white tiled floor at the Bedford Atlantic Armory located at 1322 Bedford Avenue, Brooklyn. Veterans had scars, but what the doctors witnessed was ridiculous. Delaney’s long list of injuries included a busted nose, two cauliflower ears, a patchwork quilt of knife scars and two scabby old bullet holes blasted though his bulging torso.


When the physicians wondered aloud about the origin of the wounds, Delaney spat the answer through a mouth full of gold teeth, “A lot of little wars around New York.” Little did the army doctors know, Delaney was actually Monk Eastman, the toughest goon ever to swing a lead pipe on Manhattan’s Lower East Side.


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Monk Eastman had survived turn of the century street wars of the Lower East Side, and the trenches of the First World War.



Monk Eastman Joins O’Ryan’s Roughnecks


Addled by opium and fresh out of prison, Eastman needed to a change. Time was running out for the middle-aged gangster. The day after his release in 1917, the ex-con headed home to Brooklyn to enlist in the 106th regiment of the 27th Infantry Division of the New York National Guard, a force aptly named O’Ryan’s Roughnecks for its commander Major General Frank O’Ryan.



Monk Eastman enlisted for WWI at the Bedford Atlantic Armory located at 1322 Bedford Avenue.


Bedford Atlantic Armory: Monk Eastman Enlists


Monk must have marveled at the red-pressed brick castle on Bedford Avenue. Constructed in the Romanesque Revival Style, the architectural firm of Fowler & Hough the Bedford Atlantic Armory was built in 1891 with a 136-foot tall corner tower.


Scholars cannot say for sure what drove the forty- four-year-old gangster to join the 27th. Perhaps Eastman was following the example of his father Samuel who fought in the Battle of Bull Run. Some historians suppose that Monk just wanted to turn his life around and kick his opium habit. Now a member of New York’s 27th Infantry Division, the 44-year-old gangster prepared to bring his own brand of terror to the trenches of the First World.


Monk Eastman enlisted in the 27th infantry division here in the castle like Bedford Atlantic Armory (Image via Wikipedia).

Monk Eastman enlisted in the 27th infantry division here in the castle like Bedford Atlantic Armory (Image via Wikipedia).


Shipping Out: Trench Warfare School Camp Wadsworth


On August 30th 1917, Eastman and the 27th shipped out to the most intensive trench warfare school in the United States at Camp Wadsworth, South Carolina. In their training, the recruits faced diluted chlorine gas, trench clearing drills, and all the other horrors of the Great War.




Platoon Sergeant Hank Miller recalled that the men teased Eastman, calling him “pop” because of his advanced age, but in basic training the elderly doughboy amazed his much younger comrades. The old man could outrun anybody in the unit. When Eastman hit a bayoneting dummy, he nearly tore it in half. Delaney’s secret eventually came out and the taunting ended: pop was Monk Eastman, the infamous Bowery desperado.




Bowery Brawler in the Trenches


The prospect of fighting on the side of New York’s deadliest brawler thrilled the young recruits, and the doughboys were soon ready for anything, for the gangster instructed the men in the Eastman school of no holds barred gutter fighting. By now, Eastman served as the linchpin of the 106th’s morale when the 27th docked in France.


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Eastman was once the prince of the Lower East Side, but opium addiction and prison sentences destroyed his kingdom.


Monk on the Poperinghe Line


On July 9, Eastman and the 27th marched to the Poperinghe Line in the Ypres Salient to put a stop to the rampaging forces of Crown Prince Rupprecht of Bavaria and his Sturmtruppen assault troops.


British command charged the Roughnecks with holding the line behind Dickbushe Lake against the Prince’s seasoned storm troopers. Eastman and his comrades dug in under the shadow of Mont Kemmel and Vierstraat Ridge, two German strongholds bristling with heavy artillery. For days and nights, shells and shrapnel rained down on the 27th’s position.


As the barrage tore holes through the unit, the first waves of elite Sturmtruppen assault teams came over the top and engaged Monk’s unit in hand-to-hand combat. It was during this bitter defense that the first tales of Eastman’s heroism began to circulate. At night, Monk led his own forays into no man’s land. When the Germans nearly overran the trenches, Monk met the Kaiser’s finest with his tattooed knuckles. While rescuing a fallen comrade, a rifle round blew through the old brawler’s hand, but he wrapped the wound and fought on.


Major General Frank O’Ryan leader of the 27th Infantry Division.

The hard nosed Major General Frank O’Ryan leader of the 27th Infantry Division.


Taking Vierstraat Ridge


O’Ryan ordered Colonel Franklin Ward, commander of the 106th, to seize the heavily fortified Vierstraat Ridge. Under the cover of a barrage, Ward and the screaming men of the 106th went over the top. A German staccato of machinegun fire pined down the entire regiment, but Monk broke the stalemate with a fist full of Mills Bombs. According to the New York Tribune,


“The German gunners caught sight of him. They could not depress their gun sufficiently to hit him and Monk crawled forward and blew them up…”–The New York Tribune



Crown Prince Rupprecht of Bavaria.


Monk Eastman Is Wounded


In the attack, bullets shredded Eastman’s backpack and shrapnel sliced through his leg, but the destruction of the German machinegun nest allowed the 106th to take the ridge. Because of the success at Vierstraat, in three days time, the 27th captured Mount Kemmel, Rosignoll Wood, Petite Bois, Plateau Farm, and hundreds of prisoners, but Monk was not there celebrate. He was laid up in a field hospital nursing his wounds. On September 4, the 27th moved to prepare for one of the greatest battles in the war, the taking of the impregnable Hindenburg Line, gateway to the German Homeland.

When Monk got wind of the plans in the hospital, he went renegade. The gangster stole away into the night, fleeing the hospital half-naked and barefooted. According to Lieutenant J.A. Kerrigan,

“He escaped from the hospital, equipped himself from a salvage dump, joined his company, and was in action throughout the entire Hindenburg line show.” –Lieutenant J.A. Kerrigan.


Cracking the Hindenburg Line


Unfortunately for the 27th, the Hindenburg attack made the battle in the Ypres seem easy. According to Maj. General O’Ryan’s memoirs, the line represented the “rock of Gibraltar of German moral.” Devised by Field Marshal Paul Von Hindenburg, the position consisted of three concrete trenches surrounded by three belts of barbed wire, mines, and machine gun nests.



Field Marshal Paul Von Hindenburg, engineer of the Hindenburg line of barbed wire, mines and machine gun nests.


Paul von Hindenburg

German reinforcements stood in the nearby St. Quintin Canal Tunnel, a bombproof 50 meters deep brick tunnel built by Napoleon Bonaparte. The tunnel housed thousands of German reinforcements on canal boats who could be shuttled anywhere on the line unseen and under cover. The task of cracking this impressive nut naturally fell to the 106th, and Eastman’s regiment served as the battering ram that led the first charge.


On the morning of September 27, the 106th stormed though a hail of machineguns and artillery fire to capture a precarious foothold from which the main assault on the St. Quintin tunnel would be led. Amid this carnage, Monk showed a tender side when the 106th seized a group of German prisoners, including a cocky teenager, one of the Americans attempted to ram a bayonet though the arrogant boy’s chest. Monk stopped the solider with only a few words, “Let him alone he’s only a kid.” he said. By now the troops knew not to argue with the gangster.


Monk Becomes Stretcher Bearer


With the position secure, the 106th withdrew to the rear, but Monk begged the head surgeon, Major Larson, for permission to remain as a stretcher-bearer. According to Major Larson,


“All through the time that men of his company were resting Eastman served in the front line trench, carrying back wounded men.”-Major Larson


A few days later, the 27th demolished the canal tunnel and broke the Hindenburgh Line. The war was over.

Monk is Pardoned by Governor Al Smith


On March 25, 1919, the 27th marched down Fifth Avenue as heroes, but Monk’s feats of heroism were all but unknown. The gangster’s officers prepared a surprise for the hero of the 106th upon their return home. Colonel Ward, Major Scott Burton, Captain James Conroy, and Lieutenant Joseph Kerrigan presented a massive tome of over one hundred letters and signatures to Governor Smith asking for Eastman’s pardon, and on May 8, 1919, the Governor forgave Edward Eastman’s past crimes.



The New York newspapers sang the mobster’s praises and spoke of the power of reform. Unfortunately, while reporters paid the mobster compliments, Monk was back to his old tricks working as an enforcer for the Brains of Broadway Arnold Rothstein. The gangster-turned-doughboy-turned-goon did not live to see fifty. Click to read The Death of Monk Eastman. www.infamousnewyork.com/2015/01/09/the-death-of-monk-eastman-union-square/

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Murder at the Metropole: The Charles Becker Herman Rosenthal Case 147 West 43rd Street

Address: 147 West 43rd Street

Status: The Casablanca Hotel


By the summer of 1912, every gangster, gambler and politician in New York City wanted Herman Beansie Rosenthal dead. The pro-gambler had upset the apple cart, spilled the beans and went to the press, revealing a massive web of police corruption after the coppers smashed up Beansie’s casino- a casino that was under the paid protection of NYPD Lieutenant Charles Becker.


Charles Becker, Charley Becker, Herman Rosenthal, Arnold Rothstein, Big Tim Sullivan, Tammany Hall, NYPD, Lefty Louie, Gyp the Blood, Big Jack Zelig, Hotel Metropole, Gangs of New York, Harry Horrowitz, Satan’s Circus, Tenderloin, 147 West 43rd Street, Tony DeNapoli’s, Hotel Casablanca, Damon Runyon, Bat Masterson, Abe Attell, Bill Consindine, Becker Rosenthal Case, Rosenthal Murder, Fanny Brice.

Owned by Tammany Hall powerbroker, Big Tim Sullivan,The Metropole boasted a 24 hour liquor license and a casino managed by Arnold Rothstein.


Murder at the Hotel Metropole:

The Becker Rosenthal Case

Just after Midnight, July 12, 1912, Rosenthal strolled into the Metropole Café, now Tony DeNapoli’s, with an arm full of newspapers plastered with headlines of his allegations against Lt. Becker. At 4 AM a gray Packard taxi roared up to the Metropole with a cargo of gunmen, coked to the gills, from the dreaded Lenox Avenue Gang.



1-The Gray Murder Car which carried the gunmen assassins. 2-Herman Rosenthal, The Gambler, whose murder is charged to the New York Police System. 3- The brightly lighted streets of the murder. Rosenthal was shot under the big electric sign in the center of the picture. 4- Rhinelander Waldo, New York’s police commissioner. Mrs. Harry Vallon, Wife of the Murder Council member Frank Vallon. 6,7– Gyp the Blood and Lefty Louis, Two of the gunmen held for the murder. 8-Sam Schleps


There in the blinking electric lights of Times Square, Lefty Louie Rosenburg, Harry “Gyp the Blood” Horrowitz and Dago Frank Cirofici waited for their prey. When Rosenthal exited the Metropole, the gunmen opened fire. According Historian Mike Dash:


“… Investigation would eventually establish that at least three rounds were fired. The first bullet had missed its target and embedded itself at head height deep in the wooden frame of the Metropole’s front door. But the second had struck Rosenthal in the face, passing through his cheek and jaw…” Mike Dash, Satan’s Circus.


The murder would go on to become the crime of the century, adding yet another gritty layer to the Hotel’s gangland history.



A popular gangland resort and casino, the Hotel Metropole was located at 147 West 43rd Street. It was the scene of the murder of Herman “Beansie” Rosenthal in 1912.


Up in the Old Metropole

Located a dice roll away from the Big Street, Broadway, the Hotel Metropole opened in 1910 at 147 West 43rd Street and became a nightlife nexus of the Tenderloin district known as Satan’s Circus. The first hotel in New York City with running water in every room, a pair of pro-gamblers known as the Consindine Brothers (George and Bill), operated the hotel on behalf of Tammany Hall powerbroker Big Tim Sullivan. The Metropole became the sparkling diamond of Big Tim’s hustles. Now called the Casablanca hotel, the building is one of the most storied gangland hotels in all of Manhattan.


Charles Becker, Charley Becker, Herman Rosenthal, Arnold Rothstein, Big Tim Sullivan, Tammany Hall, NYPD, Lefty Louie, Gyp the Blood, Big Jack Zelig, Hotel Metropole, Gangs of New York, Harry Horrowitz, Satan’s Circus, Tenderloin, 147 West 43rd Street, Tony DeNapoli’s, Hotel Casablanca, Damon Runyon, Bat Masterson, Abe Attell, Bill Consindine, Becker Rosenthal Case, Rosenthal Murder, Fanny Brice.

Today, the Metropole is called the Hotel Casablanca.


The murder would leave an indelible mark on the annuals of American criminal history, even appearing in the Great Gatsby:


“The old Metropole,” brooded Mr. Wolfsheim gloomily.  “Filled with faces dead and gone. Filled with friends gone now forever. I can’t forget so long as I live the night they shot Rosy Rosenthal there.”-F Scott Fitzgerald, The Great Gatsby


Bat Masterson, Damon Runyon and Nicky Arnstein

A human stew of Broadway characters called the Metropole home because of its 24 Hour liquor license, making the hotel’s cafe a hotspot for showgirls, gunmen, boxers, newspaper reporters and gamblers.

Wild West gunfighter turned New York newspaperman, Bat Masterson and his protégé Damon Runyon were regulars. Bat lived upstairs near noted cardsharp Nicky Arnstein, future husband of Ziegfeld Girl, Fanny Brice. Cole Porter would immortalize the wiseguys and cardsharps of the Metropole in his song, Ace in The Hole.



Arnold Rothstein’s Casino

Arnold Rothstein, the Brain of Broadway, managed Big Tim’s gambling parlor on the second floor. The opulent casino featured faro tables and roulette wheels. Some of the biggest crap games New York City history went down in the Metropole. It was also in the Metropole where Abe Attell, a former champion featherweight boxer, caught the attention of Arnold Rothstein becoming The Brain’s bagman and enforcer. Attell served Rothstein well during fixing of the 1919 World Series, insulating the gangster from criminal prosecution, serving as a go between for Rothstein and the Chicago White Soxs.


Arnold Rothstein

 Arnold Rothstein. the Brain of Broadway, managed the Metropole’s casino.


Enter Herman Rosenthal

A small time gambler with big dreams, Herman Rosenthal became a regular at the Metropole’s all night card games. With the help of Big Tim Sullivan’s bankroll, Rosenthal set up a lavish gambling den a few blocks north at 104 West Forty Fifth Street where the gambler lived with his wife Lillian. After a police raid smashed the joint, Rosenthal turned to police Lieutenant Charley Becker, cutting the corrupt police officer in on 1/5 of the house’s take. Unfortunately for Rosenthal, letters to Mayor Gaynor’s office reported the operation. The raids on the casino continued and Beansie Rosenthal went to the Newspapers to squeal.


The Jewish Mob:

Lefty Louie, Gyp the Blood, and Big Jack Zelig

By this point Rosenthal’s enemies led by a powerful syndicate of gamblers, gangsters, and police Lieutenant Charley Becker wanted the canary dead. With the help of Lower East Side Jewish Mobster Big Jack Zelig, a contract was placed on Rosenthal’s head to be carried out by Lenox Avenue Gang members Lefty Louie and Gyp the Blood. According to Herbert Asbury:


“Gyp the Blood was a sheriff and gorilla at the cheap dances of the East Side…He possessed extraordinary strength, and frequently boasted that he could break a man’s back by bending him over his knee.”-Herbert Asbury, Gangs of New York


The triggermen struck on July 12, 1912 and all of New York reverberated in the wake.


Lefty Louie gyp the blood

Two eastside gunmen (seated), Harry “Gyp the Blood” Horrowitz and Lefty Louie Rosenburg, were sentenced to death for the slaying of Herman Rosenthal.


The Chair For Charley Becker

Lt. Becker and the Lenox Avenue gang were found guilty of the crime and were sent to the electric chair at Sing Sing. The Metropole Hotel still stands today and is known as the Hotel Casablanca.

 Charles BeckerNYPD officer Charles Becker was sentenced to death for the crime.

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