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The Eastmans

Founded by Monk Eastman, the Eastmans were a tough bunch of Jewish gangsters from Lower East Side Manhattan. Archenemies of the Five Points Gang, their story is one of corrupt politicians, a dirty cop and spectacular gangland shoot-outs.

Edward Osterman, or "Monk Eastman" Edward Osterman was born in Brooklyn in 1873, the son of a Jewish immigrant who ran a Kosher restaurant. He went under numerous alias’ such as Eddie Delaney, William Delaney, Joe Marvin, and Joe Marrio. However, he was known best as Monk Eastman, and he lent this name to his gang, the Eastmans. The Eastmans started out as muggers and burglars, and later moved on to more lucrative gambling, prostitution and extortion rackets.

An animal enthusiast, Eastman opened a pet store on Broome Street in Manhattan’s Lower East Side, but he grew so attached to the animals that he could not bear to sell a single one. Instead, he kept a shop-full of cats and pigeons as his own pets. He was rarely seen without a pigeon on his shoulder or a cat under his arm, and was known to hand out severe punishments to anyone being cruel to animals. Oddly enough, he never viewed cruelty to humans in the same light.

In the days before the pet shop, he 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. He once beat up a customer for no other reason than to add a new notch and "make it an even 50". His gang would carry out beatings for $15, stabbings for $25 and murders for $100. This is the kind of activity that lead ambulance drivers at the Bellevue hospital to nickname the Accident and Emergency Ward the "Eastman Ward".

At the height of it’s power, the Eastman gang had approximately 1200 members and a territory between Monroe Street, 14th Street, the Bowery and the East River. The gang worked for corrupt Democrat politicians William "Boss" Tweed and Richard Croker. The Eastmans intimidated voters and were themselves "repeat voters", meaning they used assumed names to vote several times in the same election. Despite many arrests, these political contacts protected Eastman from conviction for his numerous thefts, assaults, vice crimes and murders.

The predominantly Italian Five Points Gang lead by Paulo Vaccerelli aka "Paul Kelly" worked in the same area as the Eastmans and the two gangs were fierce rivals. Territorial fighting broke out between them in 1901 and Monk was lucky to survive an assassination attempt when one of Kelly’s men shot him twice in the abdomen. The bullet entry wounds were only minor scars on a man who went through life with a broken nose, cauliflower ears and lacerations almost covering his face and body.

In 1903, a battle broke out between the two sides when members of the Five Points Gang held up a gambling hall owned by the Eastmans. The Eastmans opened fire and killed one of the Five Pointers. The raiders quickly retreated to the nearest phone and called Paul Kelly. Kelly told his men to round up as many gang members as possible, then he rushed to Rivington Street in a carriage. Meanwhile, Eastman 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. Hearing the gunfire, the Gophers showed up on Rivington Street and shot into the fray, not really paying attention to which side they hit. Approximately 500 police officers arrived making for a dramatic four-way firefight. The conflict ended only when the last of the Five Pointers, Eastmans and Gophers ran out of ammo. Amazingly, only 3 people were killed and 7 injured.

After Rivington Street, the media put intense pressure on the corrupt politician "Big Tim" O’Sullivan. The battle was so highly publicized that O’Sullivan told the two gangs that every gambling joint and brothel they owned would be subject to police raids until the sides made peace. Monk Eastman and Paul Kelly were forced to publicly 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 intervened when Eastman was beating someone up in 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.

Max "Kid Twist" Zwerbach became the new Eastman boss. As far as the Five Points Gang was concerned, the war was over, but for Kid Twist, the issue had just been put on the back burner. Instead, Zwerbach concentrated his aggression on Irish gangster Richie Fitzpatrick. Zwerbach lured Fitzpatrick and one of his men to a "peace-meeting" and killed them. Shortly afterwards, Kid Twist’s lieutenant Vach "Cyclone Louie" Lewis murdered several members of Fitzpatrick’s gang.

4 years later, Kid Twist and Cyclone Louie got into a fight in a Manhattan bar. Their rival, Louis "The Lump" Pioggi broke his ankle when he jumped out of a first-floor window in order to escape his attackers. A member of the Five Points Gang, Pioggi complained to his boss Paul Kelly. Kid Twist and Cyclone Louie were murdered shortly afterwards.

Zwerbach’s successor was Big Jack Zelig, a racketeer from the Bronx who relocated to Manhattan’s West Side. In 1911, Lt. Charles Becker of the NYPD hired Zwerbach to kill Herman "Beansie" Rosenthal. Becker was using his position in the police force to extort money from New York criminals. As Becker’s demands grew more and more outlandish, Rosenthal refused to pay and threatened to expose him. Undoubtedly, "Beansie" thought his association with big-time mobster Arnold Rothstein would protect him, but he was wrong.

Zelig hired Harry Horowitz to carry out the murder. Known as "Gyp the Blood", Horowitz lead a group of thieves called the Lennox Avenue Gang. Four members of the Lennox Avenue Gang shot Rosenthal in the Metropole café. The killers were Gyp himself, "Dago" Frank Cirofici, Loius Rosenburg, and Jacob Seidenshuer. All four were arrested along with Jack Rose, the getaway-driver. When Lt. Becker delayed in bailing the men out, Rose got nervous and confessed during interrogation. Becker and the shooters were jailed for murder, but fortunately for the Eastmans, Rose did not know about Big Jack Zelig’s involvement. The less fortunate Lennox Avenue Gang could not withstand the blow dealt by the convictions of it's best men, and the remaining members broke away to other gangs.

During a botched hold-up in 1911, an injured Zelig was abandoned by his two lieutenants, Jack Sirocco (a defected Five Pointer) and Chick Tricker, and was arrested. The Eastmans were still working for Democrats Tweed and Croker who flexed their political muscles to have him released. Knowing that their boss would seek revenge, Sirocco and Tricker sent their friend and fellow Eastman, Jules Morell, to kill Big Jack. Foolishly, they let a man named Ike the Plug in on the plot, and he warned Zelig of Morell’s intent.

One night, a group of the Eastmans went out with Morell and plied him with drink. Once he was drunk, they lead him to Big Jack Zelig who shot him down, sparking off a civil war. The two sides battled for several months until Zelig was shot dead on October 5 1912 by "Red" Phil Davidson. Monk Eastman was actually released from prison shortly afterwards, and assumed leadership of the gang for a brief period before returning to prison for another 8 months for robbery. Sirocco and Tricker took over the Eastmans but the gang had been torn apart by the civil war. Severely reduced in size and lacking the political might of former leaders, the gang quickly disintegrated.

In 1914, Monk Eastman was released from prison and joined the 106th Infantry of the US Army’s 27th Division: "O’Ryan’s Roughnecks". Under the alias of William Delaney, he served in France during the Great War and afterwards, newspapers were filled with stories of his courage and heroism in the trenches. Eastman was put on a pedestal as the model "reformed prisoner". After his conviction, Eastman had lost his US citizenship, but with the vocal support of the press and his fellow war veterans, the Governor of New York conceded and restored his citizenship.

However, there is much doubt as to the extent of his rehabilitation. One story tells that in 1918, he stole a car belonging to Jules W. Arndt, aka "Nicky Arnstein". Arnold Rothstein was one of New York’s most powerful gangsters and he made it his business to retrieve his friend Arnstein’s car. Rothstein knew Eastman from Hammerstein’s Victoria Theatre where the two men played craps back in 1898. Rothstein, then only 16 years old used to loan money to other gamblers, and paid Eastman to extract money from those who didn’t make their repayments on time. Now, twenty years later, Eastman discovered that the car he stole belonged to a friend of Rothstein. Eastman personally delivered the car back to Arnstein and made his apologies, saving his skin for the time being.

Eastman met his end on December 27 1920. He had been drinking in the Bluebird Café, a speakeasy in Manhattan. After he left that night, he was shot five times outside the Bluebird by Jerry Bohan, a corrupt Prohibition agent with whom he had been drinking inside the Bluebird. Despite his self-defence plea, Bohan was convicted of murder. Two of Eastman’s army friends took up a collection and raised the money for a military funeral attended by over 4,000 mourners.


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