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Archive for the ‘Gangs of New York’ Category

mulberry-bend

Address: Mulberry Street Between Worth and Bayard Streets

Status: Partially Demolished in 1897 Now Columbus Park

 

A maze of back alleys and hidden passageways, the Mulberry Bend on Mulberry Street was a gathering place for generations of New York’s underworld. From the Dead Rabbits to the Gambino Crime Family, the Bend’s horrific conditions served as an incubator for the gangs of New York. Today, only a tiny sliver of this infamous neighborhood still exists.

 

All that remains of Mulberry Bend today, is a tiny sliver of land on the east side of Columbus Park.

All that remains of Mulberry Bend today, is a tiny sliver of land on the east side of Columbus Park.

 

According to 19th century social reformer Jacob Riis:

“Where Mulberry street crooks like an elbow within hail of the old depravity of the Five Points, is “the Bend” foul core of New York’s slums.”–Jacob Riis, How the Other Half Lives

 

Mulberry Street was the aorta that pumped life though the slums of the Five Points. Located between Worth and Bayard Streets, The Mulberry Bend was a place where the poorest of the poor scrambled to survive. A home for the unwanted and unwelcome, the street existed as a multi-racial, multi ethnic, polyglot community, unplanned and predating the city’s grid system.

 

The Mulberry Bend. 1)Ragpicker’s Row 50 ½ Mulberry Street 2) Bandits Roost 59 ½ Mulberry Street. 3) Bottle Alley 47 Baxter Street.

The Mulberry Bend. 1)Ragpicker’s Row 50 ½ Mulberry Street 2) Bandits Roost 59 ½ Mulberry Street. 3) Bottle Alley 47 Baxter Street.

From Country Lane to Urban Slum

 

In the days before the American Revolution, the street was named for a grove of Mulberry trees on the banks of the Collect Pond, one of Manhattan’s freshwater reservoirs. The Pond’s marshlands forced engineers to route the country lane in a west to east bend, which would become Mulberry Bend.

 

By 1810, Mulberry Street became urbanized. Heavy industry congregated around the Collect Pond. Slaughterhouses, potters and blacksmiths choked the shores of the Collect, while raw sewage from the slums of Mulberry Street ran into the water, transforming the pond into a polluted bog.

 

The freshwater Collect Pond quickly became a toxic bog. It was drained in 1817 and became the Mulberry Bend.

The freshwater Collect Pond quickly became a toxic bog. It was drained in 1817 and became the Mulberry Bend.

 

In 1817 the City Council drained the pond by digging a canal, which still runs under Canal Street today. The city then filled and graded the empty pond and Mulberry bend was born.

 

Street was a gathering place for generations of New York’s underworld. Image via Museum of the City of New York

Mulberry Street was a gathering place for generations of New York’s underworld. Image via Museum of the City of New York

The Bend

 

By the time of the Potato Famine, the Bend ranked as one of the densely populated urban areas in the world. For most of the 1800s the Bend’s population consisted of Irish immigrants and free African Americans, but by the 1880s an onrush of Italian overtook the squalid streets. Day and night on the bend, peddlers hawked stale bread, questionable meats and stolen goods.

 

The slums of Mulberry Bend in the heart of the Five Points. Image Via the Museum of the City of New York.

The slums of Mulberry Bend in the heart of the Five Points. Image Via the Museum of the City of New York.

 

Squeezed by landlords and forced to live in apartments crammed well beyond capacity, diseases wracked the neighborhood annually, accumulating an astronomical infant mortality rate. In 1888, over 3,000 infants died on Mulberry Street before reaching 6 years of age.

 

Mulberry Bend was the epicenter of incredible poverty. Image via the Museum of The City of New York.

Mulberry Bend was the epicenter of incredible poverty. Image via the Museum of The City of New York.

 

The poorest in the Bend, lived and worked in maze of back alleys stretching over to Baxter (then Orange St.) Street. With few options and little hope, it’s no wonder the denizens of the Bend’s back alleys turned to a life of crime.

 

The Mulberry Underground

 

A warren of hidden passageways and back alleys, with insidious names such as Rag Picker’s Row, Bandit’s Roost and Dynamite Alley, the underworld utilized the ramshackle architecture of the Bend to their advantage, hiding from both the police and sanitary inspectors. According to Jacob Riis:

 

“The whole district, is a maze of narrow, often unsuspected passageways-necessarily, for there is scare a lot that has not two, three, or four tenements upon it, swarming with unwholesome crowds.”–Jacob Riis, How the Other Half Lives

 

Rag Pickers, the lowest echelon of New York society, congregated in Rag Picker’s Row, another of the Bend’s enclaves where they would collect their rags scavenged from the city’s trash. Nearby at 50 ½ Mulberry Street, visitors could find Bandit’s Roost, a favorite haunt of murderers and thieves dating back to the antebellum period.

 

Bottle Alley. Image Via Museum of the City of New York.

Bottle Alley. Image Via Museum of the City of New York.

A Lineage of Crime

 

The Dead Rabbits, the Roach Guards, the Whyos, The Five Pointers and eventually the Mafia all called Mulberry Bend home. During the Civil War, the Dead Rabbits, an Irish street gang,  headquartered their gang on Mulberry Street, where they committed many depredations during the Draft Riots. By the 1870s, a gang called the Whyos, known for their call “Why-o”, dominated Mulberry Street and much of the Five Points. Naturally, the warrens of Mulberry Bend became their homeland. According to Herbert Ashbury:

 

“The Whyos maintained their principal rendezvous in Mulberry Bend, slightly north and east of the Five Points proper…”–Herbet Ashbury, Gangs of New York

 

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Bandits Roost. Image via the Museum of The City of New York.

 

As demographics changed around the turn of the century from Irish to Italian, the Mafia emerged as lords of the Bend, but their reign would not last long. Appalled by the horrid conditions, the infant mortality rate and the rampant murder, photo-journalist Jacob Riis declared war on the slums with an unknown technological advancement, the camera.

 

Jacob Riis: Photo-Reformer

 

Armed with nothing more than his camera, Riis explored the back alleys, saloons and rear tenements, documenting the squalor of the Bend and other slums. Riis published his work in a landmark text titled: How the Other Half Lives. A best seller, Riis’ book  led to the demolition of Mulberry Bend.

 

Photo journalist and social reformer, Jacob Riis, revealed the horrors of The Mulberry Bend.

Photo journalist and social reformer, Jacob Riis, revealed the horrors of The Mulberry Bend.

 

The End of Mulberry Bend: Columbus Park

 

In 1897, the city completely demolished Mulberry Bend, except for a tiny sliver of land. In its place, the city erected the Five Points Park, hoping that the clean air and grass would reduce crime and give children a play to play. The largely Italian population of Mulberry Street renamed the park Columbus Park in 1910.

 

The city demolished Mulberry Bend in 1897 and created Mulberry Bend Park which was later renamed Columbus Park.

The city demolished Mulberry Bend in 1897 and created Mulberry Bend Park which was later renamed Columbus Park.

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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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Thumb-Metropole-Hotel-Charles-Becker-Herman-Rosenthal-

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

Address: 147 West 43rd Street

Status: The Casablanca Hotel

 

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

 

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

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

 

Murder at the Hotel Metropole:

The Becker Rosenthal Case

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

 

Herman-Rosenthal-Murder-Charles-Becker

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

 

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

 

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

 

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

 

Hotel-Metropole-Herman-Rosenthal-Murder-Charley-Becker-Map

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

 

Up in the Old Metropole

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

 

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

Today, the Metropole is called the Hotel Casablanca.

 

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

 

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

 

Bat Masterson, Damon Runyon and Nicky Arnstein

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

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

 

 

Arnold Rothstein’s Casino

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

 

Arnold Rothstein

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

 

Enter Herman Rosenthal

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

 

The Jewish Mob:

Lefty Louie, Gyp the Blood, and Big Jack Zelig

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

 

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

 

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

 

Lefty Louie gyp the blood

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

 

The Chair For Charley Becker

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

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

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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.

11th_Street_Catholic_Cemetery

 

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

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

IMG_0100

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.

 

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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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

The Wickedest Man’s Dance Hall and bordello at 304 Water Street circa 1868

Location: 304 Water Street

Status: Demolished

Priests, police, and just about everybody in Manhattan called John Van Allen the Wickedest Man in New York, and he reveled in it. A born self-promoter, if Allen had been alive today he probably would have had a reality television series.

 

In a twenty-year life of crime, Allen set the tabloids aflame with his wacky antics even attracting the attention of Mark Twain who described the forty-five year old dancehall owner and pimp 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.”—Mark Twain

 

John Allen Wickedest Man In New York

John Allen the Wickedest Man in New York and his son, Chester, a lad “hell on reading, writing, praying and fighting.”

 

House of Rum and Prostitution

Strangely enough, Allen and his criminal brothers Westley (Wess), Theodore (The.), Martin and Jesse were the sons of a wealthy Presbyterian minister. John amassed over 113 arrests for running disorderly houses across the city, but his most infamous den was a dancehall located at 304 Water Street.

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

Known for dancing prostitutes and cheap rum, Allen’s Dancehall would earn him the title: Wickedest Man in New York

Demolished to make way for the Brooklyn Bridge in 1870, his three story bilious green, bordello offered several dance floors, an orchestra pit and booths for sex. According to Herbert Asbury’s Gangs of New York, Allen staffed his club with twenty prostitutes dressed in,

 

“…low black bodices of satin, scarlet skirts and stockings, and red topped boots with bells affixed to the ankles.” 

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

The Wickedest Man In New York holds court in his bar.

A Breathing Hole of Hell

According to Edward Winslow Martin’s Secrets of the Great City published in 1868, Allen’s dancehall was:

 

“…a breathing hole of hell—a trap door of the bottomless pit… where lousy loafers lurk..”

 

Allen lived above his bar with his wife, seven daughters and son, Chester, a lad who according to his dad was “hell on reading, writing, praying and fighting.”

In reality, Allen probably wasn’t the wickedest man on Water Street by a long shot (the title rightly belonged to Tommy Hadden), but after his ceaseless campaigning for the title, the moniker stuck when the Allen transformed his whorehouse into New York City’s wackiest religious revival.

 

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

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Shang Draper, Thomas Shang Draper, Tenderloin, Al Smith, Casino, 6-8 West 28th Street

Location: 6-8 West 28th Street

Status: Standing

 

He was like John Dillinger, Al Capone and Jesse James rolled up into a 19th century bundle. Generous, refined, wealthy and deadly, Tomas “Shang” Draper ran one of the most opulent casinos in Manhattan here at 6 West 28th Street in the heart of Satan’s Circus.

 

King of Safecrackers

The Italianate brownstone casino represented the pinnacle of Shang Draper’s life of crime.  Former king of the bank robbers and safecracker extraordinaire, Shang was one of the best petermen in the country, blowing bank vaults from New York to Minnesota.

Thomas Shang Draper, Shang Draper, 6 West 28th Street, Manhattan Savings Institution Robbery, Manhattan Savings Institution, Fredericka Marm Mandelbaum, Marm Mandelbaum, Casino, George Leonidas Leslie, Satan’s Circus, Al Smith

Shang Draper’s casino was located at 6 West 28th Street

Fencing with Marm

Together with society figure and architect, George Leonidas Leslie, alias Western George, Shang and Leslie plundered millions, heisting the Waterford Bank in 1872, the North Hampton Bank in 1876, and the Manhattan Savings Institution in 1878.  The gang specialized in looting securities, which they fenced through Fredericka “Marm” Mandelbaum.

 

A Taste for the Finer Things

It seemed that Shang got a taste for the finer things from Leslie, whom he eventually shot and dumped in the wilds of the Bronx. With his bank robbing fortune, Draper headed for the Tenderloin district, a place where the glitterati of Manhattan’s Gilded Age went to drink, whore, smoke opium and gamble in style.

 

Standing six feet tall in his silk stockings, Tomas Shang Draper was a giant by 1800s standards, and he had a personality to match.

Standing six feet tall in his silk stockings, Tomas Shang Draper was a giant by 1800s standards, and he had a personality to match.

With the backing of lottery king, Al Adams, Shang settled at 6 West 28th Street, just off of fashionable 5th Avenue. To attract wealthy patrons from nearby hotels and Madison Square Garden, Shang remolded the entire building.

 

Shang’s Casino

He threw up onyx pillars on the first floor. Crimson silk curtains covered the windows. Oil paintings valued at $100,000 lined the walls. The buffet was all you could eat. The plates were china and the goblets were cut glass.

 

The roulette wheel spun for no less than $25 a twirl, and guests, who included politicians, prizefighters, millionaires and vaudevillians, could expect to find high stakes poker, faro and chuck-a-luck.

 

According to Automats, Taxi Dances and Vaudeville author, David Freeland:

 

“Future governor [and presidential candidate] Al Smith was once reputed to have stayed at the faro tables for fifty-two hours straight.”

 

Underworld Fortress

Big money meant big security. To guard against raiding cops and stickup gangs alike, Shang installed a battering-ram proof door equipped with a mechanical cross bolt that dropped into the doorjamb. Behind the door, a steel cage provided secondary defenses, while a sliding steel grate protected every window. Simply put: it was the coolest fortress in town.

 

Thomas Shang Draper, Shang Draper, 6 West 28th Street, Manhattan Savings Institution Robbery, Manhattan Savings Institution, Fredericka Marm Mandelbaum, Marm Mandelbaum, Casino, George Leonidas Leslie, Satan’s Circus, Al Smith

One of the most opulent casinos in Manhattan, Shang Draper turned this brownstone into a fortress with steel grates and a battering-ram proof door.

Coppers!

But the Parkhurst Society wanted the club closed. On October 14, 1902 police officers raided the casino, but the heavily fortified club took hours to breach, giving Shang’s customers enough time to scramble out of a secret back staircase on the building next door. The police eventually recovered hundreds of thousands of dollars in Shang’s safe. After the raid Draper retired to Hot Springs Arkansans.

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James Street Gang, Johnny Torrio, Al Capone, Frankie Yale

The territory of Johnny Torrio’s James Street Gang

Location: James Street

Before the St. Valentine’s Day Massacre and Prohibition put him on the map, Al Capone received his bachelor’s degree in gangsternomics courtesy of Johnny “The Fox” Torrio, a future mafia chieftan who got his start as the leader of the James Street Gang.

A dormouse of a man with button eyes and a nose like a thimble, Torrio could only be described as one of the finest criminal mastermind’s of the 20th century, and it all started on James Street, a tiny sliver of a street that is one of the last remaining vestiges of the old Corlear’s Hook neighborhood.

Life in crime came early for Torrio. As a boy he worked in his stepfather’s illegal moonshine den at 86 James Street. In 1904, the urchin started promoting boxing matches, where he met the bantamweight fighter and gangland kingpin, Paul Kelly. Kelly, a suave racketeer whose real name was Paolo Antonini Vacarelli, captained the Five Points Gang, a mob that ran Little Italy and fixed elections for Tammany Hall.

Much of James Street was demolished during the 1940s.

Much of James Street was demolished during the 1940s.

Kelly took an immediate liking to Torrio, teaching the young gangster how to dress, speak, and steal. In return for his mentorship, Torrio founded a Five Points auxiliary called the James Street Boys to aid Kelly and the Yakey Yakes during the Eastman Wars.

From there “The Fox,” moved on the Irish controlled Brooklyn Navy Yard with the help Frankie Yale and a teenaged enforcer named Al Capone, whom Torrio introduced to the Manhattan underworld through his James Street connections. Torrio gave up his mini- New York empire when Chicago’s prostitution overlord, Big Jim Colosimo, requested Torrio’s aid to protect his Windy City whorehouses. “The Fox” left New York but always remembered his roots by importing James Streeter gunmen like Roxie Vanella (https://infamousnewyork.com/2013/09/27/the-mayor-of-james-street-robert-roxie-vanella/ ) and Frankie Yale to do his dirty work. Torrio called for Capone in 1921, and the pair went on to make gangland history.

Torrio

Johnny Torrio

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