Archive for the ‘Monk Eastman’ Category

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.


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



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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Thumb 11th_Street_Catholic_Cemetery2


It was a neighborhood of potent ugliness, a wasteland of rubble and rust strewn with monstrous gas tanks, and belching gasworks, pumping out noxious sulfurous fumes, the byproduct of cooking bituminous coal to produce the gas which fed the streetlights of New York. Authorities around the turn of the last century called the slum the Gas House District, and a hunchback mobster was its king.


A rare view of one of the last gasworks in the Gas House District circa 1938., years after Humpty Jackson's reign.

A rare view of one of the last gasworks in the Gas House District circa 1938, years after Humpty Jackson’s reign.


A bare-knuckled Dickensian creature, well-armed and well-read, Thomas “Humpty” Jackson and his band of colorfully nicknamed hooligans like Monahokky, The Grabber, Candy Phil, Maxie Hahn, Spanish Louie, and the Lobster Kid, terrorized the neighborhood from the ruins of an ancient cemetery that has long since vanished.


Thomas "Humpty" Jackson lead his turn-of-the-century gang from the 11th Street Catholic Cemetery.

Thomas “Humpty” Jackson lead his turn-of-the-century gang from the 11th Street Catholic Cemetery.


According to Herbert Asbury’s Gangs of New York, the cemetery was, “…bounded by First and Second Avenues and Twelfth and Thirteenth streets,” yet today, not a single headstone remains, and anyone searching for the remnants of the boneyard will be befuddled by Asbury’s erroneous directions.


The infamous hunchback of East 11th Street, Thomas Humpty Jackson

The infamous hunchback of East 11th Street, Thomas Humpty Jackson


The 11th Street Catholic Cemetery


Built in 1832 to replace Old St. Patrick’s overflowing graveyard on Mulberry Street, the Eleventh Street Catholic Cemetery stretched from the east side of First Avenue to Avenue A. Fifteen years, and forty thousand corpses later, tenements sprouted up around the graveyard, and the city banned burials in Manhattan, forcing the Eleventh Street cemetery to lock its gates.



In 1883, the New York Times wrote,

“The old cemetery has been neglected and has become a scene of desolation. The fences have been broken by boys, and… it has become a great source of trouble to the church…” –The New York Times, 1883


It’s impossible to say when Humpty, who was born in 1879 according to the 1925 census, first jumped the fence of the cemetery.  After he quit the rackets and started giving interviews (hotlink), Humpty would later reminisce:


“Take the Gas House District… no playgrounds and no gymnasiums. Nothing for strong kids to do…but commit depredations…”—Humpty Jackson


And depredations he committed.


Humpty’s First Pinch


At the age of thirteen, Jackson caught his first pinch for stealing a horse blanket. For his heinous crime, he was sent to the reformatory on Wards (Now Randall’s) Island, turning the little hunchback into a lifelong cop hater. By twenty, Humpty was a professional stick-up kid, heisting grocery stores up and down the Lower East Side, which eventually landed Jackson his first holiday in the penitentiary on Blackwell’s Island.


After his release, Humpty Jackson earned his first newspaper mention for stabbing a policeman in the hand and neck, but by now the Hump was a well known character in the Gas House District, the domain of Tammany overlord Silent Charley Murphy.


Tammany Boss Silent Charlie Murphy employed Jackson as a key election rigger.

Tammany Boss Silent Charlie Murphy employed Jackson as a key election rigger.

Election Rigging 101:

Tammany Hall Recruits Jackson


The veteran election rigger immediately saw potential in the young hunchback. With the help of Big Tim Sullivan, Humpty was soon stumping for Tammany Hall. Repeat voting, ballot box stuffing, and good old Republican slugging, granted Humpty a license to steal. Humpty later bragged to Collier’s Magazine:


“…we’d gang the joint. Smack a couple of Republican ballot watchers over and swipe the boxes and throw them in the river.”


Armed robbery, assault, and vagrancy charges disappeared like magic courtesy of Tammany Hall, and with political backing, Jackson carved out a fiefdom strong enough to repel both Monk Eastman and Paul Kelly’s Five Points Gang. But the infamy brought the heat. According to the newspapers, every mugging, shooting, and petty theft in the district was the work of the Humpty Jackson gang.


The Battle for 11th Street


The tipping point came on the night of September 12, 1904. That night Humpty and his pals were lounging on the headstones in their graveyard hangout. The gangsters sat up and took notice after they spied Fredrick Keller, a former member of the gang, strolling down 11th Street.


The remains of the 11th Catholic Cemetery today.

The remains of the 11th Catholic Cemetery today.


In instant the wolves jumped him. A fist fight broke out, and one of Humpty’s goons put a revolver to Keller’s head and pulled the trigger, but the gun misfired.


Keller broke away and sprinted to the Police precinct on 5th Street. Seeing an opportunity to put Jackson away for good, Capt. McDermott raced to the cemetery with five plainclothesmen, Detective Ed Reardon, and a team of reservists. The small army of cops put the collar on Humpty Jackson, the Riley Brothers, and William Noble and marched them back to the precinct.


An Army of Mobsters


Suddenly an army of 30 mobsters appeared on 11th Street, a pistol shot rang out and the cops ducked for cover. They returned fire with their service revolvers and roaring gun battle erupted.


From the tenements, bricks and potted plants and bottles rained down on the police. Jackson pulled a hidden revolver and beamed four shots at Detective Ed Reardon, those shots would earn Humpty 2 ½ years in Sing Sing where the hunchback was treated to a regimen of: “Twelve hours a day in solitary…paddling, and thumb hanging exercises…” However, his time in the can wasn’t all bad.


Humpty spent the majority of his stretch reading: Herbert Spencer, Thomas Paine, Darwin, Voltaire, and Huxley. He even penned a book on police brutality. When he emerged from the big house, Humpty was smarter and tougher than ever before, but unfortunately things had changed on the sidewalks of New York.


Humpty Jackson on the Transformative Power of Reading

Humpty Jackson on the Transformative Power of Reading


When he got out of prison, Humpty headed back to his home away from home, the 11th Street Catholic Cemetery. As he began to reorganize his mob, the police, led by Detective Ed Reardon, torqued up the pressure. Police arrested Jackson on sight for vagrancy, disorderly conduct, and anything else they could pin on the hunchback.


The Gat in the Hat


To prevent the law from planting weapons on him, the ingenious mobster sewed up his pockets so that:


“Cops couldn’t slip a gun in a gun in my pocket and pull me in for carrying a rod…”


But the pressure grew, making it impossible for Humpty to steal for a living.

When Jackson opted to go strapped he,


“…Invent[ed] a pistol holster for my hat. I got away with that for a long time until a young cop got wise and slapped me on the nut with his night stick.”


Humpty Jackson often carried a pistol in his hat.

Humpty Jackson often carried a pistol in his hat.


Unfortunately, sewed up pockets and his secret holster did little to keep the eccentric mobster out of the papers, and Tammany’s support waned. By 1908 the Hall had backed a new tough, former light weight prize-fighter and Chinatown bouncer, Jimmy Kelly.


The Feud With Jimmy Kelly


Called the Human Pin cushion by his pals, Kelly, whose real name was Giovanni DeSalvio, was as rough-and-tumble as they came. Kelly and his Chinatown mob, opened the Folly 212 East 14th on the outskirts of Humpty’s turf, and it was clear that a bloody confrontation loomed.

Humpy Jackson's rival, Jimmy Kelly, John DeSalvio would go from gangster and nightclub owner to Tammany Hall politician.

Humpy Jackson’s rival, Jimmy Kelly. Kelly’s real name was John DeSalvio. DeSalvio would go from gangster and nightclub owner to Tammany Hall politician.

On November 1, 1908 Tammany Hall and Big Tim Sullivan symbolically backed their new goon when the Jimmy Kelly Association held a ball at Tammany Hall.


Enraged that Big Tim had backed his rival, Humpty stalked Kelly, his wife Stella, and his bodyguard Chink Marello to restaurant on 15th Street and 3rd Ave. When Kelly left the restaurant to get a bottle of wine, Humpty followed him to 13th Street, raised a revolver and shot the ex-prizefighter in the neck. As Kelly lie dying in a pool of blood, Humpty put another bullet in his groin for good measure. Kelly survived.


Humpty Goes Down


After the shooting of Kelly, Tammany abandoned the hunchback and his downfall quickly followed. Arrested for stealing a $1,000 seal skin coat from the Adams Express Company, Humpty was tried as a habitual criminal. Facing a life sentence, Humpty pled guilty and was sent to Sing Sing for three years.


Return to the Graveyard


When Humpty returned from the joint, he found that the world had changed. The gasworks were closing down because of the adoption of electricity, but more strikingly the 11th Street Cemetery had vanished. While he was in Sing Sing, the church sold the property and moved the remains of 5,000 bodies to section 4b of Calvary Cemetery in Queens, leaving behind the remains of 35,000 burials.


After going straight, Humpty and his wife Bertha opened a pet shop.

After going straight, Humpty and his wife Bertha opened a pet shop.


Humpty Quits the Rackets


With the closing of the cemetery an era had ended, and the Hump decided to go straight. Humpty later told a Collier’s reporter:


“…I got Tired, tired of being pinched every time somebody I never heard of did something, tired of the same old burglar racket, slugging punks and not being able to go around outside my own district.”


Jackson settled down, got married, opened a pet shop, and went on to a new found fame as the hunchback gunman who had quit the rackets.

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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


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


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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Five Points Headquarters

57 and 59 Great Jones Street

Status: Standing


There weren’t many places in old New York where a goon could order up a beer, eat a plate of spaghetti, and kick back and watch a bare-knuckle boxing match, except, for the Little Naples Café and New Brighton Athletic Club located at 57 and 59 Great Jones Street.


These two squat interconnected buildings once headquartered the Paul A. Kelly Association, an organized hoard of repeat voters, ex-pugilists, pimps, and gangland heavies otherwise known as The Five Points Gang. The mostly Irish and Italian Five Pointers controlled every hustle west of the Bowery and were the sworn enemies of Monk Eastman’s Jewish mob that dominated everything east of the Bowery.



Paul Kelly’s New Brighton Athletic Club (right) and the Little Naples Cafe (left) today. Jean Michel Basquiat would later die of an overdose in the loft that was above the New Brighton.


Paul Kelly Gangland Dandy


Their leader, Paul Kelly, proprietor of the combination eatery and boxing arena, was a bucket-load of contradictions. The name he went by was Irish; yet the gangster was an Italian whose real name was Paolo Antonio Vaccarelli. Well
quaffed and well spoken, Kelly played the part of the gangland dandy who could bang with the best of them.


According to Richard Harding Davis, Kelly was,

“exquisitely scented, wearing silk socks, silk ties to his tan shoes, with rings on his well-kept fingers…”




But Kelly’s manicured digits didn’t fool anyone in the know. A former flyweight boxer and catch-as-can wrestler of much renown, the leader of the Five Points Gang was always willing to throw down. Like the time Kelly floored Jake Shimsky, a 6 foot, 230 pound Eastman Lieutenant, with a left hook that put the giant’s brain to sleep.


Spoke Five Languages


To have said that Kelley was smart would have been an understatement. In addition to English, he spoke Spanish, French and Italian. To take advantage of a loophole, which legalized boxing matches in privately chartered athletic clubs, he opened the New Brighton Athletic Club in 1904 in a Civil War era stable located at 59 Great Jones.


A Gangland Nexus Is Born:

The New Brighton Athletic Club and Little Naples Cafe


Now free to hold bare-knuckle bouts without police interference, the customers flooded in. To feed his hardboiled clientele, Kelly opened up the Little Naples Cafe next door, and a gangland nexus was born. On any night, a hoodlum could find Chick Tricker, Louie the Lump, Kid Griffo, Rough House Hogan, 14th Street Biff Ellison, and the wrestler Leo Pardillo lounging around the bar.


Paul Kelly, Paolo Vaccarelli, Monk Eastman, Eat Em Up Jack McManus, Monk Eastman, Biff Ellison, Leo Pardillo, Five Points Gang

The Little Naples Cafe, 59 Great Jones St., was the headquarters of Paul Kelly’s Five Points Gang


Eat ‘Em Up Jack McManus


To keep the peace, Kelly brought in his best gorilla, the famed bar-room bouncer, Eat ‘Em Up Jack McManus, but even McManus couldn’t keep the peace, and the gunplay was regular.


In less than a year, Kelly’s bare fisted spaghetti kingdom began to unravel. Led by Chick Tricker, Jimmy Kelly, Jack Sirocco, and Biff Ellison, the mutinous troop of Five Pointers loaded up their gats and plotted to knockoff the boss.



Paul Kelly (right) poses with bar-room bouncer Eat ’em Up Jack McManus.


Five Points Lightning


The slugs started to fly just before dawn on May 26, 1905 when words between McManus and Tricker escalated into a full blown pistol duel in font of the Little Naples.


Dodging and weaving from stoop to stoop, McManus blasted a few slugs into Tricker’s calf and left him for dead in the gutter, but Eat ‘Em Up Jack Should have finished the job. Days later Kelly lost his greatest strong armer, when McManus was killed by a Tricker Assassin armed with a lead pipe.


Jack Sirocco and Chick Tricker’s Revenge


Months later Jack Sirocco came looking for revenge for Tricker’s shooting, and earned a bullet in his arm. With their leadership full of lead, the Tricker Sirocco gang sent another team of torpedoes to the Little Naples the following Thursday.


With barking pistols in their hands, Biff Ellison and Razor Riley stormed into the Little Naples spewing bullets. The attackers caught Kelly and his bodyguard Bill Harrington completely by surprise. A shot pierced Harrington’s lung killing him instantly. Another shot knocked Kelly’s hat from his head, and bullet sliced through the sleeve of his coat.


As the shots rang out, showgirls dove for cover, and the lights were doused. For five minuets Kelly and his attackers traded gunfire in the darkened bar. The Little Naples and New Brighton Athletic club were closed by the police shortly thereafter. With his clubhouse padlocked, Kelly changed his name back to Vacarelli, moved uptown, and remade himself as a labor racketeer.

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