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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.

 

Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

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-WWI-Bedford-Atlantic-Armory-Map

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.

 

Monk-Eastman-Infantry-Traning-WWI-27th-Infantry-Division-Camp-Wadsworth

 

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.

 

Monk-Eastman-Trench-Warfare-School-27th-Infantry-Division

 

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.

 

Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

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

 

DSC_0385

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.

 

Paul_von_Hindenburg_(1914)_von_Nicola_Perscheid

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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Socks Lanza, Yakey Yake Brady, Fulton Fishmarket, South Street Seaport, Corlears Hook, The Bridge Café, Roxy Vanella, Vito Genovese, Lucky Luciano, NYPD, Harbor Patrol, Socco the Bracer, Patsy Conroy, Saul and Howlett, River Pirates, Paris Cafe, NYPD Museum

Click to enlarge map in a new window.

Murder, mayhem and river pirates are not among the listed tourist attractions at Manhattan’s South Street Seaport, but that’s exactly what a sightseer would have encountered during much of the district’s history.

Once a major port in the 1800s, this salty strip of land on the East River attracted merchantmen from around the globe for its deep waters and ice free docking, but with millions of dollars of cargo arriving daily came the dreaded specter of New York’s earliest organized crime syndicates—river pirates.

Today’s boutiques were once brothels and the gastro pubs rum holes. To walk these streets at night was to play a real-life game of Lets Make a Deal. Behind door number one: a whorehouse. Behind door number two: a dog-fighting pit. Behind door number three: shanghaiing, murder and death. Allow this South Street Seaport Walking tour to take you back to the days when river pirates and mobsters ruled South Street.

 

Gangs of the South Street Seaport Walking Tour Map

 

1 First Precinct: NYPD Museum

Location: 100 Old Slip, www.nycpolicemuseum.org

Status: Closed for Renovation

1st precinct 20

There’s probably no better place to start a tour of the criminal history of the South Street Seaport than the New York City Police Department museum. Sandwiched between looming skyscrapers, the landmarked 1909 neo-Renaissance First Precinct building represents the first modern police building in the U.S. and a must see for law enforcement buffs. Usually ringed with vintage NYPD vehicles parked curbside, the NYC Police Museum is under restoration because of flooding during Hurricane Sandy. When it reopens, guests will be treated to vintage uniforms, Willy Sutton’s lock picks, old mug shots, and the Tommy gun used to assassinate Frankie Yale.

 

2 Fulton Fish Market

Location: Pier 18 South Street

Status: Landmarked

Fulton Fishmarket Project Underworld Navy and the Mafia WWII

It was the heart of the Seaport and the queen of South Street, an insular, self-regulated 188-year-old world populated by fishmongers and scoundrels and sea captains and Mafiosi. Now desolate and rusty, the battered, but landmarked, corrugated metal Tin Building on Pier 17 once stood as the district’s high temple of brine. If you get there early enough and squint into rising sun you might see them, the ghosts of the fish men who toiled from 1822 to 2005 in their blood spattered aprons under the predatory gaze of the gangs of New York.

The Mafia arrived in 1919, when a twenty-year-old character exploded onto the scene. His name was Joseph Lanza, but his mafia co-workers called the 230-pound bulldozer “Socks” because of the knockout force in his meat hooks. With the help of his knuckles, the mobster organized the United Seafood Worker’s Union, Local 202, and a goon squad incorporated as the Fulton Market Watchmen and Patrol Association on behalf of Joe “The Boss” Massaria and later Lucky Luciano and Vito Genovese. Lanza died in 1968 amid the constant probes of both federal and state organized crime task forces.

The Romano twins, Carmine and Vincent, picked up where Socks left off, extending the reign of the Genovese crime family into the late 1990s. The Federal Government convicted the Romano’s for violations of the Taft-Hartley anti-monopoly act in 1981, which paved the way for Rudolph Giuliani to initiate a lawsuit that placed the Fish Market under Federal Custodianship. In 2005, the reek of fish and crime wafted from the Fulton Fish Market for the last time when the entire industry packed up for the Hunt’s Point in the Bronx.

 

3 Water Street

Location: Water Street

Most visitors who stroll over the uneven cobblestones of Water Street fail to realize that the social reformer Oliver Dryer once called this thoroughfare:

“…the wickedest block in the wickedest ward in the wickedest city in America…” –Oliver Dryer

By the mid-1800s, Sailors arrived daily on Water Street to booze and whore the night away, but the seamen were always one step away from death. Consisting of one block of bars, brothels, rat pits and gambling dens, Water Street existed as the nexus of waterfront crime—a place where pirates plotted their next score, fixed elections and wrapped the corpses of murdered sailors in chains for disposal. On Water Street violence was endemic. The dives and whorehouses and hellholes that lined this street had fitting names. There was Long Marry’s at No. 275 and Mother McBride’s at No. 340, but none were more infamous than Kit Burn’s Rat Pit.

 

4: Kit Burn’s Rat Pit

Location: 273 Water Street

Status: Landmarked

Web Kit Burns the Ratpit today 273 Water Street

Now luxury apartments, 273 Water Street once represented the heart of Water Street’s “sporting culture. Officially named Sportsmen’s Hall, Kit Burn’s Rat Pit existed as New York City’s premier dog fighting and rat baiting venue. In the pit, a gaslight illuminated octagon, eighteen inches high, sixteen feet long, and eight feet wide, Kit pitted dogs against dogs and terriers against gigantic wharf rats in gladiatorial matches that would have made the Ancient Romans blush.

The pit was a family affair, and Kit ran business with his wife and daughter, Kitty, a dame well acquainted with the business end of a wooden club. For fun Kit brought in his son-in-law Jack the Rat, a character who would bit the head off a rat for a quarter a chomp. Henry Bergh, founder of the ASPCA, eventually put the bite on the Rat Pit and closed the establishment with the help of the NYPD. For a longer story on Kit Burn’s Rat Pit: https://infamousnewyork.com/2013/10/22/kit-burns-rat-pit/

 

5: The Bridge Café

Location: 279 Water Street Status: Closed for Renovation

http://bridgecafenyc.com

Bridge Cafe, 279 Water Street, Gallus Mag, River Pirates, South Street Seaport

The Bride Café on Water Street was once known as the Hole-In-The-Wall Saloon, a vicious den of 19th century depravity.

Nearly destroyed by Hurricane Sandy, the Bridge Café exists as New York City’s last remaining pirate bar. Back in the 1870’s, the café was called the Hole-in-the-Wall Saloon. Owned and operated by Jack Perry and his wife, Mag Perry, the infamous Gallus Mag. A suffragette, before women’s suffrage became popular, Gallus earned her nickname from the unthinkable act of wearing trousers, rather than dresses, and holding them up with galluses or suspenders. When clients gave her trouble, Gallus often bit off their ears and dropped them in a pickling jar behind the bar. One-Armed Charley Monell later took over the bar and converted the upper floors into a brothel. By the 1900s, the Bridge Cafe became a hangout for the Yakey Yake Brady gang. For a longer story Gallus Mag the Bridge Café: https://infamousnewyork.com/2013/11/14/save-the-bridge-cafe-new-york-citys-last-pirate-bar/

 

6: Vanella’s Funeral Chapel

Location: 29 Madison Street Status: Open

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An original member of Johnny Torrio’s James Street Gang, Roxie Vanella (Namesake of Vanella’s funeral chapel) followed Torrio to Chicago, leaving a crime spree in his wake. After killing a corrupt police officer and beating the charges, Vanella returned to Corlears Hook in New York and opened this funeral chapel at 29 Madison Street. For the complete story on Roxie Vanella: https://infamousnewyork.com/tag/vanellas-funeral-chapel/

 

7: Yakey Yake Brady and the Rumble for Cherry Street

Location: Cherry Street

Yaley Yake Brady

They came from the west with plunder on their minds and bucking revolvers in their hands. It was hard to say why in the spring of 1903 the thousand strong Monk Eastman mob turned their greedy paws on the slums of Cherry Street, but for John “Jake Yakey Yake” Brady it meant war.

Raised in the shadow of the Brooklyn Bridge, Yakey Yake carved out a fiefdom in the Irish slum known as The Gap in the northerly hollow of Cherry Street. A former jockey and barrel maker, Brady’s professions didn’t prevent him from mixing it up with the rowdies. Arrested dozens of times for scores of “accidental” and intentional shootings, Brady became the most feared man in Corlears Hook with a reputation so dreadful that when a longshoreman pressed assault charges on Yake; the dockworker hanged himself rather than face the hoodlum’s retribution.

When Monk Eastman came for Yake’s waterfront kingdom, the blood of gangsters turned the East River red. As the New York Sun put it:

“Under the bridge, revolver shots have echoed by twos and threes and by hundreds.”—The New York Sun, 1903

Because of the Monk’s superior numbers, Yake formed an alliance with Eastman’s perennial rival, Paul Kelly’s Five Points Gang, who had a nearby outpost on James Street garrisoned by Johnny Torrio and Roxy Vanella. To dam the tsunami of violence, the police ringed the district with undercover officers with orders to frisk and arrest any armed goons. The cops put Yakey Yake under such pressure that the gang leader wagered his barrel making firm on a card game and won a wagon team that he used to relocate to Jersey City, where he died in 1904.

 

8: The Sinking of Socco the Bracer

Location: Pier 27, Foot of Jackson Street

Flash, fire and smoke, lit up the night sky on May 29, 1873, when members of the Patsy Conroy mob exchanged gunfire with the harbor police at Jackson Street’s Pier. Earlier that evening, Joseph “Socko the Bracer” Gayle, Danny Manning, and Benny Woods hijacked a rowboat and rowed out in search of the ship, Margaret. Two skiff-borne harbor cops noticed the river pirates scampering up the ship’s anchor chain. Officers Musgrave and Kelly opened fire.

The rogues dove into their rowboat and pulled away into the darkness. A champion rower, Officer Musgrave gave chase while his partner scanned the horizon with a lantern, which was greeted by a pistol blast. The police answered with their six-shooters and traded broadsides with the thugs like a man-o’-war until a bullet tore through Socko. His companions pitched him overboard and the river bandit sunk to the bottom like a lead plated mackerel. The authorities apprehended Benny Woods the next day. Unfortunately, the Margaret sailed for China with the witnesses, ending any chance of a conviction.

9: Murder on the East River: The Saul and Howlett Story

Location: East River, Foot of Oliver Street

On the night of August 25, 1852, a pistol shot rang out from the Thomas Watson, a cargo ship anchored at the foot of Oliver Street. As Charles Baxter, the ship’s night watchman bled to death, two pirates rifled through the dying man’s clothing. The thieves then heard the rapping of a police nightstick against the cobble stone street, the signal for reinforcements in the days before police whistles.

A dozen lantern-carrying police officers sprinted to the scene, collaring William Saul and Nicholas Howlett, two river-borne rogues that Herbert Asbury incorrectly identified as leaders of the Daybreak Boys. (Former Chief of Police George Walling believed that the two men were the leaders of the Hook Gang) Whatever their affiliation, Saul and Howlett terrorized the waterfront for over a decade and the Chief credited the pair with twenty murders. The Baxter murder; however, would become one of the most sensational stories of the decade, signaling the end of the East River pirates. Saul and Howlett were found guilty of the murder were hanged in the Tomb’s courtyard on January 28, 1853. Bill “The Butcher” Poole attended the hanging to wish his river pirate friends farewell.

 

10: The Wickedest Man in America:

John Allen’s Dance Hall

Location: 304 Water Street

Status: Demolished

Wickedest Man in New York, John Allen. 304 Water Street, Brooklyn Bridge, South Street Seaport, Corlear’s Hook, 4th Ward, Westley Allen, Wess Allen, The. Allen, Theodore Allen, Gangs of New York, Herbert Asbury, Gangs of New York, Saloon

Priests, police and just about everyone else in New York City called John Van Allen the wickedest man in New York, and he reveled in it. In less than twenty years, Allen amassed over 113 arrests for running disorderly houses across the city, but his most infamous den was this now demolished Water Street dancehall.

The three-story bordello at 304 Water Street offered several dance floors, an orchestra pit and booths for sex serviced by Allen’s crew of twenty ladies of the night. A natural self-promoter, Allen set the tabloids aflame with his wacky antics even attracting the attention of Mark Twain who described Allen as, “a tall, plain, boney, fellow, with a good-natured look in his eye, a Water Street air all about him, and a touch of Irish in his face.” In reality, Allen probably wasn’t the wickedest man on Water Street by a long shot (his brother’s The. And Wes were far more wicked), but after his ceaseless campaigning for the title, the moniker stuck when the fishmonger transformed his whorehouse into New York City’s wackiest religious revival.

 

11 The NYPD Harbor Patrol

The murder of the ship watchman Charles Baxter by the infamous desperados Nicholas Howlett and William Saul alerted the public to waterfront crisis. Chief Walling commented on his battles with Saul and Howlett in his autobiography. He wrote,

“My investigations in this murder opened up to me a chapter in the annals of crime, of full horrors of which I never dreamed…human monsters prowled around our river fronts…who thought no more of the life of a man than that of a chicken.” Police Chief George Washington Walling

Following the Saul and Howlett case, the Police Department organized its first harbor patrol of several rowboats and took the war to the seas. The department purchased a steam ship named the Deer, which functioned as a fulltime floating station house. In 1858, the Metropolitan Police Force expanded the harbor unit to 57 men, six rowboats and the paddle wheel steamer, Senica. The men of the harbor police used to joke that the steamship was only fast when she was tied to the pier. The Senica was an abject failure that only made one arrest before burning to the waterline in 1880. Despite the failure of the flagship, the harbor force brought the pirates to their knees, pacifying the waters of the East River by the turn of the century and driving crime to the shores.

 

12 Meyer Hotel, The Paris Café and Project Underworld

Location: 119 South Street

Status: Landmarked

To complete your tour of the South Street Seaport, step into the Paris Café and have a drink at its original, hand-carved bar and ponder its history. Home to longshoremen, sea captains and mobsters, the Paris Café has served beer since 1873.

Constructed by alcohol merchant Henry Meyer, the Meyer Hotel and its Paris Café stood out as the poshest hotel and bar in the district. Thomas Edison, Annie Oakley, Buffalo Bill, Butch Cassidy, the Sundance Kid and Theodore Roosevelt all spent time in the building before beginning voyages to Europe and South America. When the passenger steamship lines moved their docks to the new Chelsea Piers terminal, the hotel fell into disrepair and the mafia took control.

By the 1930’s, Albert Anastasia and Louis Lepke Buckhaulter regularly met in the bar. Upstairs in the hotel, Socks Lanza orchestrated his fish empire. Socks controlled the Seaport with such impunity that the U.S. Navy came calling for the racketeer in the 1940s with an unusual proposition. They wanted him to help fight the Nazis.

Eventually with Lanza’s help, naval agents embedded themselves on the Atlantic fishing fleets to observe German submarines. Lucky Luciano was even contacted in Dannemora prison to help plan the invasion of Sicily.

For more information on Project Underworld: Allegiance between the Navy and the Mafia.

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Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

Location: Union Square, Fourth Ave and 14th Street

Status: Standing

‘Twas the morning after Christmas, 1920, when police officers stumbled on the lifeless body of Monk Eastman sprawled out in a gutter just south of the Union Square subway station. One of the toughest mugs in New York City’s history, the Monk had survived half a dozen street wars up and down the Lower East Side, several terms in Sing Sing, and the trenches of WWI. (Click to read about Monk Eastman in WWI)

Monk came back from the war a hero and won a full pardon from Governor Alfred E. Smith, but now several weeks later; Eastman was dead.

Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

Monk Eastman died in the gutter of Union Square.

Boozing at the Bluebird Cafe

Christmas evening began like most days for Eastman, with a little prohibition-era binge drinking at the Bluebird Cabaret, No. 62 East 14th Street. Monk and a pack of heavies, including corrupt Prohibition Agent, Jerry Bohan, strolled into the Bluebird, sat at their reserved table and got merry. According to Neil Hanson, author of Monk Eastman, Monk boasted to a showgirl:

 

“Do you know who I am? I’m Monk Eastman, the gang leader who made good…” –Neil Hanson, Monk Eastman

Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

Monk Eastman had survived turn of the century street wars of the Lower East Side, and the trenches of the First World War, but on the morning after Christmas, 1920; Eastman was found face down in the gutter.

The Brain’s Brawn- Arnold Rothstein and Monk Eastman

But the $144 bankroll in his pocket, the fine Witty Brother’s suit and the gold spectacles found on Eastman’s body told another story. Eastman had hired his fearsome reputation out to the highest bidder, and that bidder turned out to be the Brain of Broadway, Arnold Rothstein. Jerome Charyn noted in Gangster and Goldiggers,

 

“It seems the Monk had been bootlegging and selling dope for The Brain. A.R. was never implicated, of course.”—Jerome Charyn, Gangsters and Gold Diggers

Prohibition, Monk Eastman, Lower East Side, Prohibition, Gangs of New York, Blue Bird Café, Jerome Charyn, Gangsters and Gold Diggers, Neil Hanson, Jerry Bohan, Prohibition Agent, Blue Bird Café, Union Square Subway Station, Crime, Murder, World War I, WWI, death,

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

Monk Eastman a Rat?

Emotions were high at the Bluebird that night. Monk Eastman was running his mouth about quitting crime, making good and becoming an honest citizen, talk that made his bootlegger pals nervous. Little did he know, Eastman’s buddies had put him on the spot, and Bohan was the trigger-man.

When Eastman drunkenly stumbled onto the street, Bohan followed with a .32 caliber pistol in his hand. Just as Eastman crossed 14th street, the crooked Prohibition Agent opened fire into Monk’s back.

An eyewitness described the scene:

“A man was standing over him and as we reached the window we saw him fire four more shots into the man on the sidewalk… the murderer bent over his victim a moment, presumably to make sure he was dead…”

Bohan then hopped into a waiting taxicab and sped off into the night. Several days later, under the pressure of a police manhunt, Bohan walked into the Lee Avenue police station in Brooklyn and confessed to the crime, claiming self defense as his motive. The corrupt Prohibition Agent was sentenced to three to ten years for manslaughter (Click for newspaper story) and Eastman was buried with full military honors in the gangland funeral of the decade.

In Bohan’s version of the crime, the corrupt Prohibition Agent shot Eastman in self-defense.

In Bohan’s version of the crime, the corrupt Prohibition Agent shot Eastman in self-defense.

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Monk Eastman, William Delaney, Gangs of New York, Crime, Monk Eastman’s Murder, Owney Madden, Paul Kelly, Paolo Vaccarelli, 50 Eldridge Street, Witty Brothers.

Location: 50 Eldridge Street

Status: Standing

 

Out of all of the silk stocking wearing gangland dandies such as Owney Madden, Paul Kelly and Biff Ellison, Monk Eastman was a bit of an anomaly. He and his knuckle dragging mob terrorized Manhattan’s Lower East Side with street brawling shenanigans and epically bad fashion. According to Gangs of New York author, Herbert Asbury:

 

“[Eastman] seemed to always need a haircut… He accentuated his ferociousness… by affecting a derby hat several sizes too small…”

 

The Suit They Found Him Dead In

In addition to the ill fitting derby and bad haircut, Lower Eastsiders rarely sighted Eastman with a shirt on and without a shoulder-mounted pigeon, presumably crapping all over the place. However, the suit police detectives found Eastman dead in told a far different story. Inside of his jacket, a tag read, “E. Eastman, October 22, 1919—No 17,434—W.B.”

 

Known for wearing a derby hat several sizes too small, Monk was never a dapper mobster.

Known for wearing a derby hat several sizes too small, Monk was never a dapper mobster.

 

Monk’s Tailor

The tag belonged to the Witty Brothers, a fine clothing establishment, which catered to, “The Sort of gentlemen who recognizes the import of being well-dressed. “

 

Monk Eastman, William Delaney, Gangs of New York, Crime, Monk Eastman’s Murder, Owney Madden, Paul Kelly, Paolo Vaccarelli, 50 Eldridge Street, Witty Brothers.

 

According to the New York Times obituary of Spencer Witty, heir to the Witty clothing empire:

 

“Witty Brothers, fashioned and sold elegant men’s clothing… They used luxurious fabrics, cashmere, [and] Scottish tweeds…”—The New York Times (Click to read the article)

 

After Eastman’s murder in 1920, Henry Witty told the New York Tribune:

 

“Monk Eastman, the old time gang leader… We have made clothes for him for nineteen years. The last suit we made for him was delivered October 21, this year.” –The New York Tribune (click to read the story)

 

Perhaps the Monk was more dapper than originally thought?

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Without a whisper, a whimper or a groan, Thomas “Eat ‘Em Up Jack” McManus fell face down into his derby.

Without a whisper, a whimper or a groan, Thomas “Eat ‘Em Up Jack” McManus fell face down into his derby.

Location: NW Corner of Bleeker Street and Bowery

 

The blow came suddenly and silently. Without a whisper, a whimper or a groan, Thomas “Eat ‘Em Up Jack” McManus fell face down into his derby; his skull crushed like an egg. One hardest gorillas to ever drag his knuckles down the streets of New York, the legendary barroom bouncer could realistically hold claim to the title of: Toughest Man in New York. Now he was dead.

 

In his 1905 obituary, the New York Sun wrote,

For years back “Eat-‘Em-Up” has borne all but unchallenged the distinction of being about the toughest and most brutal of all the tough and brutal Bowery gangsters.

 

Toughest Man in New York

 

Born in Boston in 1862, McManus was seemingly destined for underworld stardom like his older brother, the infamous international safe cracker, Kid McManus. However, unlike his brother, Jack earned a living with his fists from the beginning, eventually following his knuckles to New York City as a champion lightweight prizefighter.

 

Unfortunately, the prize ring proved unsuitable for McManus’s constitution, and he quickly sunk into the employ of the underworld. Alfred Henry Lewis wrote in his 1912 book, the Apaches of New York,

 

…but a liking for mixed ale and a difficulty in getting to weight had long cured him [McManus] of that [boxing].

 

Eat Em Up Jack McManus, Kid McManus, Paul Kelly, McGurk’s Suicide Hall, Chick Tricker, Kid Griffo, Five Points Gang, Gangs of New York, Apaches of New York, Tivoli, Jack Sirocco

Eat Em Up Jack McManus was killed by Sardinia Frank on the north west Corner of Bleeker Street and Bowery.

 

Barroom Bouncing At McGurk’s Suicide Hall 

 

Without boxing, Jack reverted to the only skill he knew, fisticuffs. He became a sheriff or bouncer, bringing law and order to the toughest Bowery dives and saloons in the city like the Tivoli and McGurk’s Suicide Hall. Whirling in like a Tasmanian devil with blackjacks, fists and hobnailed boots, Jack earned the nickname Eat Em Up for eating and digesting all comers. In time, McManus’s body became a patchwork quilt of wounds and welts. His front teeth were knocked out.  A knife scar ran across his throat from ear to ear (back before one of his ears was chewed off).

That’s the way I serve ‘em.—Eat ‘Em Up Jack McManus, NY Sun 1903

 

Paul Kelly’s Five Points Gang

The mayhem artist caught the attention of Paul Kelly, and the mobster hired Eat ‘Em Up Jack as bouncer at Kelly’s Little Naples Café and New Brighton Hall, sowing the seeds of McManus’s death.

 

One night Chic Tricker, a member of the Jack Sirocco clique, drunkenly wandered into Kelly’s club and insulted the showgirls. McManus stepped in, throwing Tricker out on his ear. During the scuffle, a challenge was issued for gats on 3rd avenue. Later that night, Eat Em Up and Tricker traded pistol shots under the shadow of the 3rd Avenue “El.” Jack put two slugs in Tricker’s leg and walked away unscathed. But Tricker swore revenge.

 

The next day Kid Griffo and Eat ‘Em Up Walked down the Bowery. Just as they reached the corner of Bleeker Street, a burly hoodlum named Sardinia Frank stepped from the shadows clutching a gas pipe wrapped in newspaper, and as the New York Sun put it:

 

 …a section of lead pipe was wrapped around the base of the skull to his bulldog chin, cracking the cranium all the way.

McManus died in Belleview Hospital calling out for his beloved wife Gertrude. He was 40

years old. Eat ‘Em Up Jack McManus’s death would kick off a gangland war between Kelly and Jack Sirocco which would close the New Brighton, leaving Kelly scampering uptown for a more “respectable” life.

 

Eat Em Up Jack McManus, Kid McManus, Paul Kelly, McGurk’s Suicide Hall, Chick Tricker, Kid Griffo, Five Points Gang, Gangs of New York, Apaches of New York, Tivoli, Jack Sirocco

Paul Kelly (right) and Eat Em Up Jack McManus (left) at the New Brighton.

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Joe the Boss Masseria, Giuseppe Masseria, Joe Masseria Umberto Valenti, Lucky Luciano, Charley Luciano, John’s of 12th Street, Salvatore D’Aquila, Toto D’Aquila, 302 East 12th Street , Vito Genovese

Joe Masseria’s Revenge

Location: 302 East 12th Street 

Status: Standing

 

Smarting over the recent attempt on his life, which had left two bullet holes through his hat and another two holes through his coat, Joe Masseria plotted bloody revenge in epic Italian Renaissance fashion.

 

Toto D’Aquila’s Chief Assassin

 

The target of his wrath was Umberto Valenti, a seriously wily character who had blasted those bullet holes through Masseria’s hat and coat. According to the New York Times in 1915, Valenti was:

…alleged to have arranged more shootings than any other man in the city…

 

oe the Boss Masseria, Giuseppe Masseria, Joe Masseria Umberto Valenti, Lucky Luciano, Charley Luciano, John’s of 12th Street, Salvatore D’Aquila, Toto D’Aquila, 302 East 12th Street , Vito Genovese

In the guise of peace treaty, Joe Masseria lured Umberto Valenti to John’s of 12th Street for his last meal.

 

A former Black Hand extortionist, it was rumored that Valenti had killed over 20 men, a number of whom had been Masseria’s closest advisors. The thirty four year old Valenti was the chief assassin of Salvatore “Toto” D’Aquila, the New York Mafia’s supreme ruler, a Mafioso who was locked in vicious mob war with Masseria and his chief strategist Giuseppe “the Clutch Hand” Morello.

 

However, Masseria’s seemingly supernatural bullet dodging powers had given the hard noised, but superstitious, Valenti second thoughts. Second thoughts that had him suing for peace and walking into an ambush in one of New York’s most storied Italian restaurants, John’s of 12th Street, on August 11, 1922, a restaurant that has been used as a set on Boardwalk Empire and the Sopranos.

 

Joe the Boss Masseria, Giuseppe Masseria, Joe Masseria Umberto Valenti, Lucky Luciano, Charley Luciano, John’s of 12th Street, Salvatore D’Aquila, Toto D’Aquila, 302 East 12th Street , Vito Genovese

1.Umberto Valenti emerges from John’s of 12th Street. Lucky Luciano and another assassin open fire. 2. Valenti draws a revolver and is hit in the chest with a bullet. He staggers to a waiting taxicab and dies. 3. The gunmen shoot two innocent bystanders before disappearing into a tenement.

 

Well Dressed Gunmen: Vito Genovese and Lucky Luciano

 

Whether or not Valenti sampled the chicken parmigiana before being croaked has been lost to the winds of history. However, some time around noon, Valenti and six laughing companions emerged from their luncheon. Walking eastward, smiles turned into frowns. Suddenly, Valenti spooked and bolted towards Second Avenue as two slick, well-dressed gunmen whipped out revolvers and fired. Gangland legend holds that one of the shooters was none other than Charley “Lucky” Luciano, Masseria’s newest protégé (the other shooter was probably Vito Genovese).

 

The candle in John's of 12th Street was lit to celebrate the end of prohibition.

The candle in John’s of 12th Street was lit to celebrate the end of prohibition.

Pandemonium on 12th Street

 

As the shots flew, pandemonium broke loose on 12th Street. Whirling around, the feared assassin drew a revolver just as a bullet flew through his chest.

 

A teenage witness told the New York Times:

It was the coolest thing I ever saw. People were shrieking and running in all directions, and this fellow calmly fired shot after shot. He did not move until he had emptied his weapon. With blood spurting from his clothing, Valenti tried to raise up his pistol but his wounds prevented him from doing so. He made for a waiting taxicab, collapsing on the Northwest corner of 12th Street. (Click to read the original NY Times story)

 

Luciano’s Escape

 

Despite Valenti’s death, the friendly Luciano and his pals weren’t done yet. A crowd formed to block the gunmen’s escape so the mobsters opened fire, hitting a street sweeper and a little girl visiting from New Haven Connecticut. The shots dispersed the crowd, and the hitmen disappeared into a nearby tenement.

 

Should I Bring Pajamas? 

 

Masseria was arrested for the murder.  During his arrest, he supposedly grinned and asked the police:

… whether he would need a nightshirt remarking, that the last time he slept in the station house they forgot to give him a pillow or pajamas.

 

For a job well done, Joe Masseria elevated Luciano to a leadership position at his headquarters in the Hotel Pennsylvania. All murder charges were eventually dropped, and Masseria, on his way to becoming Joe the Boss, set his sights on Valenti’s overlord, Toto De Aquila, New York’s boss of bosses.

 

However, John’s of 12th had another infamous last meal lined up twenty years later. The victim would be Carlo Tresca.

 

Joe the Boss Masseria, Giuseppe Masseria, Joe Masseria Umberto Valenti, Lucky Luciano, Charley Luciano, John’s of 12th Street

Whether or not Umberto Valenti sampled the chicken parmigiana before being croaked has been lost to the winds of history.

 

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Location: 265 East 10th Street 

Status: Standing

He had a million names and known aliases but back when Charley Lucky Luciano was living in a tenement on East 10th Street, he was nothing more than Salvatore Lucania, an impoverished nine-year-old street urchin from the sulfur mining town, Lercara Friddi.

 

Fresh off the boat in April of 1906, the Luciana family led by the family’s ironhanded patriarch, Antonio, settled in a tenement at 265 East 10th in the slums of the Lower East Side.

 

Lucky Luciano, Charley Lucky, Salvatore Luciana, 265 East 10th Street

Born Salvatore Luciana, Charley Lucky Luciano grew up in this tenement at 265 East 10th Street. His parents would live here until 1933.

 

P.S. 10: “Worst Time In My Whole Life”

Salvatore didn’t speak a word of English when he enrolled in P.S. 10, and he took an instant dislike to authority figures. He later told Martin Gosh and Richard Hammer, authors of The Last Testament of Lucky Luciano:

…wasn’t easy to go to an American school and not know a goddamn word of English…in my whole life, that was the worst time I ever experienced, the first couple of years at P.S. 10.

With a massive inferiority complex driving him forward, Luciano formed a multi-national pack of knickers-wearing hooligans and began pick-pocketing, plundering apple carts, and most importantly—cutting school. On these same streets, Luciano met Meyer Lansky while trying to shake Lansky down for his lunch money.

Lucky Luciano, Charley Lucky, Salvatore Luciana, 265 East 10th Street

Lucky Luciano lived here at 265 East 10th Street

Salvatore Lucania: The Bad One

 

Beside himself with grief over his rotten son-of-a-bitch kid, whom neighbors called “The Bad One,” Antionio beat Salvatore for skipping school. Then he beat him for not having a job. When Antonio discovered that his son did in fact have a job; and it was crime, he beat him some more. The beatings continued and so did the stealing and the skipping of school—until truant officers caught up with Salvatore.

 

On June 25, 1911, The Board of Education sentenced the boy to the Truant School for a term of four months. Lucky Luciano later quipped:

…what a kid learns in that place is how to steal better…

 

Hats and Narcotics, A Delivery Service

 

On his release, Luciano swore to his pop that he would go straight. He got a job as a delivery boy at the Goodman Hat Company where he was struck by bight idea: while I’m out delivering hats, why not also deliver dope?

 

Days later, Luciano spotted the limousine of the local drug pusher parked in front 265 East 10th Street. The young mastermind began polishing the limo with a rag. When the pusher emerged from the building, he tossed Luciano a quarter. Hurling the quarter back, Luciano offered instead to deliver drugs, taking his first step into what would one day be a narcotics empire.

Luciano’s multi-national gang of knickers-wearing hooligans who terrorized East 10th Street must have looked something like this.

Luciano’s multi-national gang of knickers-wearing hooligans who terrorized East 10th Street must have looked something like this.

 

Salvatore Becomes Charley Lucano

The drug/hat delivery route didn’t last long. In 1916, the nineteen year old Luciano was caught with a vial of heroin stashed in a hat box. Eight months later, Lucky emerged from reform school with a brand new nickname, Charley, which of course his father detested.

The final straw came when Antonio found a stolen solid gold belt buckle in his son’s bedroom. Antonio was so enraged that he wrapped the buckle around his fist, punched Luciano and threw his son out of the apartment for good.

However, for the next sixteen years, even when he was living in the posh Waldorf Astoria and Barbizon Plaza hotels, whenever Charley Lucky Luciano was arrested, he gave 265 East 10th Street as his address, sending the coppers straight to his dear old dad’s doorstep.

Lucky Luciano, Charley Lucky, Salvatore Luciana, 265 East 10th Street

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