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Archive for the ‘Gangs of New York’ Category

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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When Herbert Asbury’s Gangs of New York last left readers with Thomas “Humpty” Jackson, the crooked hunchback gnome known for packing a revolver in his hat and a copy of Voltaire in his pocket, the gangster was composting in a prison cell upstate.

But what Asbury never told readers was that Humpy spent his three year stretch reading every book he could get his thieving paws on. Stevenson, Huxley, Darwin, Herbert Spencer, and Thomas Paine, Humpty devoured every volume in the Sing Sing library, and when he got out; the Hump decided to go straight.

Surrounding himself with books, pigeons, and toy poodles, Jackson eventually opened a pet shop on 125th Street where the mug dispensed a blend of streetwise philosophy and classical learning to anyone who would listen. Soon, he was being courted by Colliers magazine, The New York Times, The Washington Post, and a dozen little rags from around the country that all came to sop up Humpty’s wisdom on subjects as diverse as: love, prohibition, capital punishment, and the secrets of life. These are his greatest hits:

Click for more posts on Humpty Jackson

Humpty Jackson on the Transformative Power of Reading

Humpty Jackson on the Transformative Power of Reading

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

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

Location: NW Corner of Bleeker Street and Bowery

 

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

 

In his 1905 obituary, the New York Sun wrote,

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

 

Toughest Man in New York

 

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

 

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

 

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

 

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

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

 

Barroom Bouncing At McGurk’s Suicide Hall 

 

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

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

 

Paul Kelly’s Five Points Gang

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

 

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

 

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

 

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

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

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

 

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

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

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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.

Location: 279 Water Street

Status: Standing

From Schermerhorn Row to the Thomas Carpenter house, the South Street Seaport boasts not only New York’s oldest buildings, but also one of its oldest drinking establishments, a pirate bar located at 279 Water Street, but now thanks to Hurricane Sandy, the Bridge Café may have to be shuttered for good.

Booze and Blood by the Bucket

Constructed in 1794, this blood red, three story sagging wood framed structure on the corner of Dover and Water Street once housed the Hole-In-The-Wall-Saloon, a vicious den of 19th century depravity. Between the years of 1859 and 1881, the heyday of the East River pirates, the bar served up booze and blood by the bucket. In The American Metropolis, Reverend Parkhurst’s gangbusting Attorney Frank Moss called the bar:

 …a bagnio [brothel] filled with river pirates and Water Street hags.

The Infamous Gallus Mag

In 1874 the Brooklyn Eagle had this to say about the bar:

It was there that thieves and junkmen would meet to ‘put up jobs;’ it was there that men were drugged and robbed and women beaten…it was there that young thieves became graduates in crime.

And it was there that folk legend Gallus Mag bludgeoned her way onto the scene. It is impossible to separate fact from fiction in the history of Mag, the noted six foot tall cockney bouncer, who kept a small sack filled with wet sand for knocking out sailors on her belt.

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

The Bridge Café is located 279 Water Street.

A Distinguished Thief

Gallus’s real name was Mag Perry, but Water Streeters called her Gallus on account of the very un-lady like suspenders (galluses) she wore. Gallus ran the Hole In The Wall with her husband Jack, the distinguished thief whose greatest claim to fame, other beating a fourteen year prison sentence, was when he swiped Josh Ward’s championship rowing belt.

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

The Bridge Café is New York City’s last standing pirate bar.

Jack ran the front of the house, tending bar and robbing and drugging sailors, while Gallus worked clean up, biting off the ears and fingers of obstreperous bar flies. She kept those grisly trophies in a pickling jar on a shelf behind the bar that is still there today.

The Bridge Cafe

Around the 1880s the name of the bar was changed to the Bridge café, on account of the massive Brooklyn Bridge at the café’s doorstep. Before Hurricane Sandy the restaurant was akin to stepping back into the days of steam and sail, replete with an 1810 tin ceiling and an ancient mahogany bar.

Now the Bridge Café needs help. During hurricane Sandy the dining room was filled with over three feet of water, but there’s good news, according to this New York 1 article the café plans to reopen in two months. So when they reopen, why not drop in at the Bridge Café, grab a soft-shelled crab sandwich and tell them Gallus Mag sent ya?

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Kit Burns Rat Pit 273 Water Street

Kit Burns’ Rat Pit

Location: 273 Water Street

Status: Standing

If Michael Vick were alive in the 1860s he would have probably called Christopher “Kit” Keyburns’ Sporstman’s Hall home. A portly, jovial, pock-marked, sodden faced man, Kit operated a dog-fighting arena from this still-standing location. Now the third oldest building in Manhattan, this three story brick structure represented the heart of Water Street’s depravity. But today, the rat pit has gone the way of everything else in Manhattan—luxury housing.

 

Kit Burn's Rat Pit map 473 Water Street

Kit Burns’ Sportsmen’s Hall was located at 273 Water Street.

 

A Start in Prizefighting

 

As a boy, Kit learned to work illegal prizefights under the tutelage of the bare knuckle boxing champ Yankee Sullivan. During one noted bout, Kit corned for fellow Water Streeter, Charley Lynch, during an eighty-six-round slugfest that ended in the death of Lynch’s opponent.

 

The Original Octagon

 

Prizefights made Kit’s reputation, but his real claim to fame was the Water Street Pit, a gas light illuminated octagon, eighteen inches high, sixteen feet long, and eight feet wide.

Wooden bleachers reached the ceiling and seated up to five hundred, and according to Oliver Dryer,

“Some of our city members of congress, state senators and assemblymen and municipal magnates, are Kit’s patrons.”–Oliver Dryer

 

Kit Burns the Ratpit today 273 Water Street

The humanitarians spend another night at Kit Burns Sportsmen’s Hall.


Rat baiting was one of the more popular games where sportsmen wagered on how many rats a terrier could slaughter. Jack, Kit’s prized 12 pound black and tan terrier, set a world record when he killed 100 rats in 5 minuets 40 seconds. After Jack died, Kit stuffed the champion pup and mounted him on the bar. Hung on walls and nailed to tables, Kit’s clientele could find the taxidermied champions of the past.

 

Kit’s Fighting Black Bear

Kit even owned a fighting black bear, which he pitted against challengers of any species. When not fighting, the bear had his own seat at the bar until he fell ill. Not wont to waste the skin, Kit skinned the fighter and turned him into a rug.

 

Bears and rats were all fine and good, but the dandies really came for the dogfights. The rules were simple. Trainers matched dogs of the same weight to fight in officiated battle with a cadre of surgeons at the ready. If an animal did not make weight, the humanitarians at the pit lashed their dog to a treadmill in the basement and whipped their fighter until it sweated off the excess pounds.

 

Web Kit Burns the Ratpit today 273 Water Street

 

After weigh-ins, the coaches scrubbed their dogs with a scalding solution of water, soda, and castile soap. A taster then licked his dog from snout to paw to prevent the opposition from rubbing of their champion with numbing agents capable of weakening their opponent’s biting grip.

I tell you what, a greenhorn don’t stand any chance down here.Christopher Kit Burns

 

Fights lasted hours, usually ending in death or a thrown towel. After the mêlée, the tasters licked the dogs again in case, as Kit put it:

…a fellow takes out a handkerchief and throws the stuff on the dog while he is fighting.

 

A standing bet of $1000 held that Burn’s dog, Belcher, could best any canine on the planet.

 

The ASPCA Closes In

 

When Kit wasn’t fighting dogs and rats, he battled the police and the ASPCA. In one instance, the NYPD crashed through a skylight and arrested scores of patrons for disorderly behavior. Kit eventually lost his grudge match with the ASPCA when the police arrested him for animal cruelty in November of 1870. The rat baiter caught diphtheria and died after beating the charges. He was 39 years old.

 

Web Kit Burns the Rat Pit Today

This fourth floor was added to the Kit Burns’ building in the 1900s.

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When Herbert Asbury’s Gangs of New York left readers with Thomas “Humpty” Jackson, the hunchback gangster was composting like a rotten potato in a prison cell upstate.

But what Asbury never told readers was that Humpty, a hoodlum known for packing a revolver in his hat and a copy of Voltaire in his pocket, spent his three year stretch reading every book he could get his thieving paws on. Stevenson, Huxley, Darwin, Herbert Spencer, and Thomas Paine, Humpty devoured every volume in the Sing Sing library, and when he got out; the Hump went straight.

Surrounding himself with books, pigeons, and toy poodles, Jackson eventually opened a pet shop on 125th Street where the mug dispensed a blend of streetwise philosophy and classical learning to anyone who would listen. Soon, newspapers from around the country came to sop up Humpty’s wisdom on diverse subjects such as: love, prohibition, capital punishment, and the secrets of life. These are his greatest hits:

Click to read more about Humpty Jackson.

Humpty Jackson on Birds

Humpty Jackson on Birds

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When Herbert Asbury’s Gangs of New York left readers with Thomas “Humpty” Jackson, the hunchback gangster was composting like a rotten potato in a prison cell upstate.

But what Asbury never told readers was that Humpty, a hoodlum known for packing a revolver in his hat and a copy of Voltaire in his pocket, spent his three year stretch reading every book he could get his thieving paws on. Stevenson, Huxley, Darwin, Herbert Spencer, and Thomas Paine, Humpty devoured every volume in the Sing Sing library, and when he got out; the Hump went straight.

Surrounding himself with books, pigeons, and toy poodles, Jackson eventually opened a pet shop on 125th Street where the mug dispensed a blend of streetwise philosophy and classical learning to anyone who would listen. Soon, newspapers from around the country came to sop up Humpty’s wisdom on diverse subjects such as: love, prohibition, capital punishment, and the secrets of life. These are his greatest hits:

Humpty on Women

Humpty_On_Women_1

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Mike Salter. Pelham Cafe

12 Pell Street

Status: Standing

Nestled among the steaming chop suey joints and smoldering opium dens of turn of the last century Chinatown, there was a dingy saloon that spilled ragtime piano into the moonlight.

On any given night, the bar played host to a packed crowd of millionaires and murders, pickpockets and tourists, all on account of The Professor on the piano and a seventeen year old singing waiter named Izzy Baline, who would one day be known as Irving Berlin.

Mike Salter's Pelham Cafe. Birthplace of Irving Berlin.

12 Pell Street today. The site was once home to Mike Salter’s election rigging gang. The ragtime piano saloon was the birthplace of the Irving Berlin.

 

The place was The Pelham Café, headquarters of the unbelievably politically incorrectly nicknamed Nigger Mike Salter, a Russian-Jewish gangster. The papers called Mr. Salter the uncrowned prince of Chinatown, and the prince had his hands in everything: prize-fights, dice games, opium parlors, and most of all, politics. He was rumored to have killed ten men on the road to becoming Big Tom Foley’s chief election captain, and Salter’s specialty was getting out the vote.

 

The House of a Hundred Entrances

 

False registration, ballot box stuffing, and good old fashioned repeat voting earned Salter a special place in the heart of Tammany Hall. As a reward in 1904, the Hall permitted him to open a saloon in the Chinatown vice district in a tenement known as the house of a hundred entrances located at 12 Pell Street.

Salter spared no expense decorating the joint. Ivory inlaid teak furniture filled the front room. Red burlap wallpaper, framed by gold paint, lined the walls. Sawdust covered the floors, and a dense, ever-present fog of bluish cigar smoke hung above the bar, a bar that sat the A-list of the New York sporting set.

 

A Den of Ragtime and Vice

 

Characters like Big Mike Abrams, Chuck Connors, Staten Island Sally, and Hoboken Harriet, wined, dined, and danced the night away. At the bar, Sulky, a homicidal loanshark that kept a tidy ledger, served brews to gangland’s finest. Part time pugilist and full time gangster, Jack Sirocco, and his chief gorilla, Chick Tricker, could be found there on the regular.

In the back room, the Professor, “Nick” Nicholson manned a tinpan piano while Izzy the singing waiter belted out raunchy versions of hit songs that kept Chinatown abuzz.

 

Mike Salter Pelham Cafe Irving Berlin

Mike Salter’s Pelham cafe was located at 12 Pell Street in the heart of the old Five Points district.

 

Nobility Visits The Pelham

 

Word spread of Izzy’s musical talents, and Chuck Connors guided legions of celebrity slummers through the saloon’s double doors. John Jacob Astor, Sir Thomas Lipton (of tea fame), and August Belmont all came to sample the hullabaloo, but nothing could top the visit by Prince Louis of Battenberg, a Rear Admiral in the British Navy and the fourteen reporters following him.

Before leaving the prince remarked to Izzy:

I have had a delightful time, not dreariness, not weariness, and not one bit lonesome.

 

Ludwig_Alexander_von_Battenberg

Prince Louis of Battenberg.

 

When the prince attempted to tip Izzy, the singing waiter waved away the coin, exclaiming:

No, sir, it was my honor to sing.

On the Prince’s way out, Izzy and the orchestra of banjos, coronets, and fiddles stuck up a ragtime version of God Save the King.

 

The Making of Irving Berlin

By this point Salter knew he had something. Inspired by booze, he badgered Izzy and The Professor into writing a song because of the success of “My Mariucci Take a Steamboat”, a ditty written in a rival saloon on Doyers street.

 

 

The result of their collaboration was: “Marie from Sunny Italy.” The effort earned Izzy a whopping thirty-seven cents; but more importantly, the sheet music listed the lyricist as I. Berlin, and Irving Berlin was born.

 

IrvingBerlin

 

Berlin later reminisced:

It was an important song, though, because it did get me out of Chinatown.

 

However, Salter’s success was short lived. In 1907, the police arrested The Prince of Chinatown on charges of false voter registration. Marshals closed down his bar, and Salter skipped bail and skidooed off to Canada for three years. Berlin wouldn’t see his boss again until 1922, when he came to pay his respects at Salter’s Funeral.

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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.

 

Little_naples_Today2

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…”

 

Paul_Kelly

 

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.

 

Eat_Em_Up_Jack_McManus_And_Paul_Kelly

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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