The Eastman Gang
John William Tuohy
Monk Eastman was accurately known as “The Terror of the East Side” When Eastman showed up at the New York National Guard recruiting station in October 1917, the Doctors on duty were pained at the razor, knife and bullet scars on his body. He had bullet entry wounds in his stomach, which he proudly told Doctors that he had plugged with his own fingers to stop the bleeding. His nose was broken nose, mashed flat actually, cauliflower ears although the ears were barely their, having been nearly slashed off of him in various street brawls years before, and lacerations almost covering his face and body including his ankles another that ran up to his barrel chest and crisscrossed his neck and face.
Eastman (Also known as Joseph Morris, William Delaney, Edward Delaney, Joe Marvin, and Joe Marrio.) was born Edward Osterman in Brooklyn New York in 1873 (The exact date is known) to respectable Jewish immigrant parents who ran a Kosher restaurant
Eastman had an odd, considering his violent and dangerous disposition, and extreme fondness for cats and birds and eventually opened a pet shop on Broome street in Lower Manhattan. He was what one might describe as an early animal activist and grew so attached to his animal that he never sold any of them. Instead, the shop eventually became a drop off center for strays.
In about 1895, the Monk moved to lower Manhattan and managed to become a City Sheriff of New Irving Hall. Sheriffs then were more or less legally armed bouncers in bars owned by politically connected Hoods. He developed into a slovenly dresser, wearing the standard hoodlum bowler hat that was several sizes to small for his head (It was where pistols were kept) He developed a clipped, slang filled speech, to match the blackjack tucked into belt and a pair of brass knuckles on his hands. Younger hoods began to imitate his slang and sloppy clothes.
After a few years, Monk quit his position the Sheriffs office and formed his own gang, the Eastman’s who were headquartered in a dive saloon on Chrystie street, near the bowery. Here the gangsters stockpiled slung-shots, revolvers, blackjacks, brass knuckles, and weapons of the street.
Although he was known by a number of alias’ he was known best as Monk Eastman, and he lent this name to his gang, the Eastman’s, 1200 strong, a band of incredibly tough muggers, safe crackers, pickpockets, and second story burglars who eventually moved into the more lucrative fields of gambling, extortion and prostitution
The Eastman gang ruled the area between the Bowery and 14th Street, which was, for decades, a no-mans land where pitched battles were fought weekly between the Eastman’s and their rivals, the Yakey Yakes, the Red Onions and Paul Kelly’s Five Pointers.
Early on, while still in his teens, the Monk worked as a bouncer in the New Irving dance hall and carried a sawn-off baseball bat with a notch for every head he cracked. It was a rough place and Monk bragged that he had once beaten up a customer for no other reason than to add a new notch and “make it an even 50”.
He looked on it as practice since the Eastman gang carried out beatings for money, $15.00 (Which was much more then it is today) for a sound beating, a beating and a stabbing went for $25 and a murder, without the beating went for a flat $100.
He had a fondness for the black jack and bragged about his skills with the weapon but was always careful to point out that he had never blackjacked a woman or, to his knowledge murdered a woman. He did however admit to beating women and blackening their eyes.
He was vicious and so active at his trade that the ambulance drivers at the Bellevue hospital to nickname the Accident and Emergency Ward the “Eastman Ward”. At the height of it’s power, about 1890 to 1905, the Eastman gang had approximately 1200 members and a territory between Monroe Street, 14th Street, the Bowery and the East River. Its main source of money and protection came from contracts from corrupt Democrat politicians William “Boss” Tweed and Richard Croker of the equally corrupt Tammany Hall. For a fixed flat rate and consideration in legal matters, the Eastman’s intimidated voters, beat up the enemy and rounded up “Repeat voters”, people who roamed the voting polls voting several times a day under assumed names.
Working the same area was Eastman’s rival, a dapper and intelligent little thug named Paulo Vaccerelli aka Paul Kelly, leader of the equally vicious and predominantly Italian Five Points Gang.
Vaccarelli Above) was born around 1876 in Italy and later immigrated with his family to New York City. He established himself first as a professional bantamweight boxer (Where he changed his name, Irish fighters generally drew a bigger ticket) and then later as a gang leader
Kelly's headquarters as it was and today (Below)
Unlike the rough and ignorant Eastman, Paul Kelley dressed well, in a conservative fashion, he was, by standards of the day, well educated, soft-spoken. He could speak English, Italian, Spanish and some French and went out of his way not to act as a gangster.
Kelly (right) with his bouncer "Eat Em Up" Jack McManus
As a result, unlike Eastman, he was able to move easily among the different levels of society and was more effective as a leader. He held court at the New Brighton Dance Hall, essentially a dive on Great Jones Street and like Big Jim Colosimo’s place in Chicago, it was frequented by the New York upper class when they felt the need to slum. But in the end, Kelley was no better or no worse then Eastman, he was a street punk, a thief and a pimp who headed a terrorist gang of dangerous thugs thought to number at least 1500 strong. The gang controlled the area between Broadway and the Bowery, and Fourteenth street, City Hall Park, the Five Points District in Manhattan’s Lower East Side, Chatham Square, the Bowery and part of Chinatown. From his gang came Chicago’s Johnny Torrio, Frankie Yale and Al Capone.
At the time, the Five Point’s (The name derives from the five pointed star once formed by the intersections of Anthony, Little Water, Orange and Mulberry Streets) was New York’s premier slum, by 1900, the height of the street gangs power, the once massive Irish ghetto had more or less become an immigrant Italian neighborhood. It was beyond poor, it was impoverished and forgotten. Five Points was, more or less, an Irish neighborhood, but by 1900 Italian immigrants had flooded into the area.
It was lined with slaughterhouses and malaria broke out regularly due to the filthy conditions and the damp ground, which covered what, had once been a small pond. It was densely overcrowded (About 3000 people per half mile) and filled with violent, senseless crime area. Garbage and chamber pots were dumped out of the windows onto the streets.
In 1832 alone, full one-third of the people of the Points succumbed to cholera. In 1854 alone, one out of every 17 people died. It was home to approximately 270 saloons and over 500 bordellos. Barefoot children wandered the streets unsupervised, most of them dressed in rags, playing on the bodies of dead horses and around puddles of human waste. Their idols were the hundred, perhaps thousands of hoods who roamed the neighborhoods. By age eight or nine, most of them would be gang members as well.
Five Points was the home to gangs like the Dead Rabbits, Forty Thieves, Kerryonians, Chichesters, Plug Uglies, Roach Guards and the Shirt Tails, wanted murderers, thieves and pickpockets all.
Both gangs grew out of the dirt-poor Jewish, Italian and Irish immigrants who flooded into New York in the late 19th century, for whom a life of crime was often the only alternative to starvation.
Monk Eastman’s feud with Paul Kelly began over a strip of territory between Mike Salter’s dive on Pell street and the Bowery. Eastman claimed domain over the territory from Monroe to Fourteenth streets and from the Bowery to the East River. Kelly stated flatly that his kingdom included the Bowery and any spoils found in this area.
As the Five Pointers grew in size and increased their rackets, it was only natural that territorial fighting broke out between them and in 1901 the Monk barely escaped an assassination attempt when one of Kelly’s men shot him twice in the abdomen. The Monk lived and the war was on.
Two and a half year later, in the summer of 1903, a street battle broke out between the two sides when the Five Points Gang held up a gambling hall owned and guarded by the Eastman’s.
The heavily armed Eastman’s opened fire and killed one of the Five Pointers. The remaining robbers ran off and regrouped several blocks Away and phoned Paul Kelly, giving him a completely different version of event over what had actually happened (Kelly had not sanctioned the robbery) Kelly rounded up his men and rushed to Rivington Street in a carriage. Meanwhile, the Eastman’s had called in reinforcements and the two gangs clashed in the middle of the street. Fighting continued for almost an hour over a two-mile-long battlefield. Over 100 gangsters took part, some of them being members of an Irish gang called the Gophers, who showed up and started firing pistols in to the fray, not caring who they hit.
The Gopher Gang. Future gang boss Owney madden is the fourth back row
In all, about several hundred (estimates rang from 100 to 200) combatants were in the fight that took place over a two mile area, eventually, after five hours, beaten off the streets by 500 patrolman, but the fight only ended when the gangsters ran out of bullets. Remarkably, only three people were killed and seven injured. The Rivington Street riot was too much, even for Tammany Hall.
“Big Tim” O’Sullivan, paid by Tammany to keep the gangs in check, delivered the bad news. Because of the media attention on the brawl, all of the gangs operations were going to be raided and shut down for a while. It was all for show, but it had to be done.
Big Tim Sullivan
To sooth over the political bosses and the newspapers, Monk Eastman and Paul Kelly were forced to shake hands at party hosted by the Democrats.
When war threatened to erupt once more, the Sheriff of Manhattan Tom Farley suggested that the two gang leaders fight man-to-man, the winner gaining complete control over the Lower East Side. Kelly and Eastman agreed, but afterwards there were disagreements over who had won the contest. Monk Eastman was not around long enough to see the fresh outbreak of violence.
In 1904, a member of the Pinkerton Detective Agency stopped Eastman from beating a man senseless in broad daylight on a Manhattan street. Eastman fired off 12 shots at the private investigator and was arrested shortly afterwards. On February 2, Eastman was convicted of the assault and received a 10 year sentence in Sing-Sing prison.
With the Monk away in prison, the Eastman’s fell under the command of the far less violent Max “Kid Twist” Zwerbach. For several weeks’ peace reigned on the streets and as far as the Five Pointers were concerned, with Eastman in jail, the war was over. However, as far as Kid Twist and the Eastman’s were concerned, the war wasn’t over, it was temporarily halted.
Eventually Kid Twist invited an Irish gangster named Richie Fitzpatrick, an alley of the Five Pointers, to a peace conference and stupidly Fitzpatrick went. Kid Twist killed him immediately. Shortly afterwards, Kid Twist’s lieutenant Vach “Cyclone Louie” Lewis murdered several members of Fitzpatrick’s gang. Since the Five Pointers couldn’t prove the killing and needed to concentrate on business, the Fitzpatrick murder was overlooked. Four years later, Kid Twist and Cyclone Louie got into a fight in a Manhattan bar with Louis “The Lump” Pioggi, a noted Five Pointer. Outnumbered, Pioggi leaped from a second story window to escape his attackers, breaking his ankle in the fall. Pioggi took his complaint to Paul Kelly and shortly afterwards both Kid Twist and Cyclone Louie were ambushed and killed.
Following Kid Twist to the leadership of the Eastman’s was Big Jack Zelig, a racketeer from the Bronx who relocated to Manhattan’s West Side. In 1911, a Lt. Charles Becker of the New York Police hired Big Jack Zelig to kill Herman “Beansie” Rosenthal. Becker was using his badge to extort money from New York criminals. Most paid, but as his demands grew more and more outlandish, Rosenthal refused to pay and threatened to expose him, assuming wrongly that the protection money he paid to Arnold Rothstein would protect him from Becker.
Big Jack Zelig
Charles Becker was originally from Sullivan County in upstate New York, and moved to New York in 1888 working as a bouncer for while In the Bowery and gained a reputation as a two fisted fighter who could handle himself. It was at this point that he met Monk Eastman.
Through Eastman, Becker probably met Big Tim Sullivan, then a state senator and Tammany’s man in the Tenderloin District (Now the area of Times Square, where Madison Square Garden sits between 7th and 8th Avenues, stretching from West 31st to West 33rd, on the western edge of the old district. Manhattan’s world renowned Garment District, home to one-third of all clothing manufactured in the United States, lies partly in the old Tenderloin. ) who oversaw all graft and bribery in Manhattan. Sullivan placed Becker on the police force in 1893.
Becker wasn’t much of a cop. Several times he was investigated and brought to departmental trials on charges of brutality and false arrest. In 1896 he mistakenly shot and killed an innocent bystander while chasing a burglar and then tried to cover up the shooting by claiming the dead man was a known burglar. He was suspended for 30 days.
In 1898, Becker jumped into the Hudson River to rescue a drowning man. Then it was learned that Becker has paid the man $15 to jump in the river so Becker could be a departmental hero and hold on to his job. As punishment, the department transferred him to the 16th precinct AKA the Tenderloin, the heart of corruption and easy money.
The Old Fourth Ward AKA the Tenderloin was located on the West side of midtown Manhattan between Fifth and Seventh Avenues. During the 1860s, its boundaries ran from around West 24th northwards to West 43rd. This area is considered the original Tenderloin.
As the 19th century progressed, the Tenderloin extended its boundaries, reaching as far south as West 20th and northwards into the West 50s and 60s. At the turn of the 19th century, the area was populated by African-Americans who had fled lower Manhattan.
New York’s first Red Light District was the Bowery however as the Bowery spiraled downwards the Tenderloin took its place.
The original Tenderloin district: from 24th Street north to 40th, between Fourth and Seventh Avenues housed Satan’s Circus, one brothel after another that offered every type of depravity that could be sold. The name came from the reformers in the 1870s.
The best known club in the area was the Haymarket, located on Sixth Avenue, near 30th Street. It opened after the Civil War, and would remain in business until 1913. It was originally a theater, the Haymarket, and then reopened as a saloon where women drank free, while men had to pay a quarter cover-charges to cover the dancing, peep shows and private sexual entertainment in private boxes.
There was Billy McGlory’s Armory Hall. McGlory had once been the leader of the Forty Thieves gang leaving it in the 1870s to enter the saloon business. McGlory’s was the favorite watering hole of the Five Points, the Old Fourth Ward and the Bowery, gangs.
The bouncers were gang members from Five Points, and they walked through the bar carrying bats and guns. Drunks were rolled by prostitutes. There was also the Cremorne at West 32nd and Sixth, the Star & Garter at West 30th and Sixth, Sailor’s Hall on West 34th, Buckingham Palace on West 27th, Tom Gould’s on West 31st and Egyptian Hall on West 24th at Sixth.
The tenderloin was the place to shop in the day and at night the place for gambling, sex of all types and all night dance halls. The area took its name from a remark by another cop Captain Alexander S. Williams AKA Clubber Williams. In 1876, he was transferred to the 19th, where his superiors hoped he could make a difference. Williams was transferred into the old Fourth and remarked “I’ve had nothing but chuck steak for a long time, and now I’m going to get a little of the tenderloin.”
On the weekends the place was packed with tourists, soldiers, drunkards, prostitutes and squads of police. The bordellos in the Tenderloin ran the spectrum, from cheap dirty houses to expensive madams. Dollar houses were located from West 24th up to West 40th. Five dollar houses littered the side streets from West 41st up to West 60th. A bordello could employ anywhere from 10 to 30 women.
The most expensive bordellos in New York City could be found on Sisters’ Row, on West 25th near Seventh Avenue. It consisted of seven adjoining buildings owned by seven sisters from New England. Callers were not admitted unless they wore evening clothes and carried flowers. They were provided with fancy clothes, pianos, champagne, food and free medical services. The women were also schooled in manners and culture. They were taught to play piano, sing and recite poetry. And they were allowed to keep a large percentage of the proceeds.
At the other end of the spectrum were the cheapest houses, along the low West 20s. The women who worked these houses were poorly fed, in poor health and poorly treated by both their customers and the owners. Even food wasn’t provided for them free. Most were ravaged with some form of venereal disease and had no access to a physician, unless they paid for it themselves.
All of the bordellos of the Tenderloin paid protection money to the police precinct. One bordello, located on West 27th Street, kept detailed records of its pay-offs. The figures are startling. In a one month period in the 1880s, the bordello, which employed 30 prostitutes, paid out the following sums:
Saturday & Sunday: additional $1.00
Sergeants: .00 every 2 weeks
Lieutenants: .50 every 2 weeks
Inspector: first-time initiation fee; then every month
Sergeants & detectives: .00 every 2 weeks
Ordinary plain clothes officers: .00 every 2 weeks, plus gifts
The police could raise their fees at any time, and without notice. If a bordello was unable to afford the increase, the police would simply shut them down and turn the girls out into the street.
Becker became the bagman for the local police captain which earned him $8,000 a year at a time when a police officer made less then $3,500.In 1910, Police Commissioner Rhinelander Waldo formed special squads to break up the street gangs that ruled Lower Manhattan and somehow Becker was placed in charge of the unit. Becker, of course, used the unit as a legal shake down tool and grew rich. Then the Rosenthal problem happened.
Big Jack Zelig subcontracted the killing to a thug named Harry Horowitz AKA “Gyp the Blood” who led a group of thieves called the Lennox Avenue Gang.
Four members of the Lennox Avenue Gang shot Rosenthal in the Metropole café. All four were arrested. When Becker was slow in getting them released, one of the men, the getaway driver, talked and Becker was arrested. On July 30, 1915, Lt. Becker was led to the gas chamber at 5:30 AM. At the signal 2,000 volts were sent into his body but didn’t, some how, kill him. A second higher jolt did. Kid Twist was already dead, executed by the state for the Rosenthal murder.
The Eastman gang then fell under control of Big Jack Zelig. In 1911, Big Jack Zelig was wounded in a badly botched hold-up in. His two top lieutenants, Jack Sirocco and Chick Tricker, assuming he was dead, left him on the streets. Zelig was arrested, but used his political pull and was released. Sirocco and Tricker, afraid that Zelig would hunt them down for deserting him on the street, hired a thug named Jules Morell to kill Zelig. However, Zelig was warned about the murder and quickly murdered Morell. The murder did little but to spark a civil war within the Eastman’s which ended several months later on October 5, 1912 when Zelig was shot dead by a hood named “Red” Phil Davidson.
In June of 1909, Monk Eastman was paroled from Sing-Sing and returned to the East Side, but found himself without a kingdom. The Eastman’s had more or less fallen apart and the Monk was unable to put them back together again. The civil war sparked by Zelig had taken out some of the gangs best men. With little else to do, he reverted to pick pocketing and dope peddling.
From 1912 to 1917, Monk was in and out of prison on various charges ranging from opium dealing, robbery, and fighting. Then, in 1917, at age 44, he enlisted in the New York National Guard under the name of William Delaney. By all reports, as part of the 106th Infantry, 27th Division, O’Ryan’s Roughnecks, Eastman proved to be a fearless warrior on the frontlines and was decorated for crawling on his belly, under fire back into enemy lines to rescue five men under his command.
He was discharged from the service in April of 1919 and as agreed Governor Al Smith restored his citizenship. By the Monk returned to dope peddling and street crime. His day was over. In 1918, Monk stole a car belonging to Jules W. Arndt, aka “Nicky Arnstein” as close friend of mastermind of the Underworld Arnold Rothstein who had once employed Eastman as a collector for his money lending operation. Rothstein found Eastman and explained that the car belonged to a friend and Eastman personally delivered the car back to Arnstein and made his apologies.
On December 26, 1920, Monk Eastman was shot and killed in front of the Blue Bird Café, a speakeasy by Jerry Bohan, a corrupt Prohibition Enforcement Agent. Bohan put five slugs in Monk Eastman
His army buddies Hank Miller and John Boland, put up the funds for a military burial with full honors at Brooklyn’s Cypress Hill Cemetery. Over 4,000 people attended the funeral, most of them simply gawkers who never knew Eastman.
“Mr. Edward Eastman did more for America than Presidents and generals,” Boland announced. “The public does not reward its heroes. Now they are calling Mr. Eastman a gangster instead of praising him as one of those who saved America. But we’ll do the right thing by this soldier and give him the funeral he deserves.”
The Monk’s corpse was dressed in full military regalia, wearing his service stripes and American Legion pin. On his coffin was a silver plate inscribed “Our Lost Pal. Gone but Not Forgotten” As for Bohan, he was arrested for the murder and sentenced to prison on first degree manslaughter charges, severed several years and was released in 1923.