Organized crime was influenced by Jewish Americans for over 30 years after the late 1890s. Edward Osterman (known as Monk Eastman) was born in Williamsburg, Brooklyn, in 1873 and was one of the kings of NYC from the 1890s until 1904. Monk started off as a bouncer, but wound up hired killer. Other aliases Monk used were Joe Morris, Joe Marvin, Bill Delaney, and Eddie Delaney. Monk loved cats and pigeons (“I like de kits and boids”) but hated his rivals. the Five Pointers. Monk was short for Monkey because of his bullet-shaped head and mangled face, which grew uglier as a result of the amazing numbers of fights he got himself into. Monk had a broken nose, cauliflower ears, sagging jowls, no neck, and scars galore. The derby hat always worn on his messy hair was several sizes too small. The name “Monk” also came from his ability to climb walls and swing through windows.
The Eastman Gang’s many rackets in the Lower East Side included prostitution and gambling as well as strong-arm operations and voter mobilization for Tammany Hall. So many of his victims ended up in Bellevue's accident ward that ambulance drivers called it the Eastman Pavilion. The gang started out around Mangin and Goerck Streets in the notorious Corlear's Hook. The streetwalkers of Corlear's Hook are where the term “hookers” originated. When the Lower East Side became the home to so many Jewish immigrants, slum kids who would become the Eastman Gang turned into a predominantly Jewish gang. Monk Eastman also came from the Hook and was a member of the gang when it first started out, involved in petty thefts mainly.
By 1900, the gang started pimping on Allen Street where NYC's largest red light district was forming. At the turn of the century, most neighborhood brothels (or “disorderly houses”) were located between Allen and Chrystie Streets. The gang at that time was known as the Allen Street Cadets; “cadet” being slang for pimp. Often seen with loose women, the gang sold opium, ran gambling operations and (don’t forget the strong-arm work) as hired goons.
The Allen Street Cadets had their clubhouse at 64 Essex Street at the Silver Dollar Smith bar. Monk Eastman soon became the bouncer (or sheriff) and started working for Tammany Hall and other politicians running NYC. Monk was also sheriff for a bar called New Irving Hall. He carried a big club and added notches to it every time he bashed an unruly patron. According to folklore, Monk had 49 notches in the club. The gang Monk led soon was known as the Monk Eastman Gang, and then the Eastman Gang.
Monk's love of pigeons and cats led his father (a deli restaurateur) to help him open a pet shop on Broome Street, which also rented bicycles. Most of his gang members were well groomed men (called dandies) and liked to show off their wealth. Many members of the Eastman Gang rode bicycles and opened a club called the Squab Wheelman. Monk lived with his wife, Margaret, at 221 East 5th Street, just a few blocks away from Paul Kelly's New Brighton Social Club at 57 Great Jones Street.
The Eastman Gang fought for territory with the Five Points Gang, Red Onions and the Yakey Yakes. Notorious Eastman members Kid Twist and Richie Fitzpatrick both were recruited from the Five Pointers. The biggest battle between the Five Pointers and the Eastmans was on September 16th and 17th, 1903, a 4-1/2 hour battle that ended at Rivington Street under the Allen Street section of the Second Avenue elevated railroad. Tammany Hall grew tired of the two gangs, both often in their employ, feuding all the time and set up a two-hour boxing match in late 1903 between Paul Kelly and Monk Eastman. The match in a barn in the Bronx ended up a draw.
But the following year, Monk was sentenced to Sing Sing for 10 years after a February 3rd, 1904, botched mugging of a drunk (with a rich influential father), and shooting at a Pinkerton detective in Times Square. Monk spent five years in prison between 1904 to 1909. Tammany Hall tired of all the bad publicity stemming from Monk and refused to help him anymore.
When Monk went to prison, Eastman's lieutenants. Kid Twist and Richie Fitzpatrick took over parts of the gang, splitting the members between them and sparking a civil war. Kid Twist bottled his own celery tonic with his picture on it and forced all the bars to carry it.
On November 1st, 1904, Richie Fitzpatrick was shot and killed, and the rest of his former Eastman Gang members were eliminated by Kid Twist's lieutenant Vach Cyclone Louie Lewis. At 8 p.m., May 14th, 1908, Paul Kelly of the Five Points Gang arranged for Kid Twist’s (Max Zwerbach) death in Coney Island with the help of another Five Pointer, Louie the Lump Pioggi. Kid Twist’s Coney Island girlfriend was a dancehall girl named Carroll Terry.
Abe Lewis ran the Eastman Gang until 1910 when another Eastman lieutenant, Big Jack Zelig Lefkowitz took over and divided the gang again into three. One part was led by Johnny (Jack) Sirocco, owner of a Bowery gin mill heavily frequented by NYC gangsters. Sirocco wore a plaid cap pulled down over his eyes and rarely shaved. Another part of the Eastman Gang was run by Chick Tricker, who was also a Bowery saloonkeeper; at a dive called the Fleabag at 241 Bowery by Stanton Street. Zelig was killed October 5th, 1912, by Red Phil Davidson, and Sirocco and Tricker took over what was left of the Eastman Gang.
The Eastman Gang was part of the toughs that Tammany boss Big Tim Sullivan used on Election Day and for other events where violence might crop up. Kenmare Street was named for the Irish town Big Tim was born in. Other members of the 1,200-member Eastman Gang were Abe Reles, Chris Wallace, Dopey Benny Fein, Diamond Charley Torti, Lolly Meyers, Tommy Dyke, Crazy Butch, Julie Morrell, Kid Dahl, and Charles Ike the Blood Livin.
After prison, still shunned by his old gang, Monk made money selling opium and resorted to petty thievery. In 1917, at the start of WW1, 44-year-old Monk Eastman enlisted in the infantry, using the name William Delaney. His street fighting was the perfect training ground to become a professional war hero. His bravery and courage on the battlefield were skills honed as leader of the Eastman Gang. He served in France with O'Ryan's Roughnecks, the 106th Infantry Regiment of the 27th Infantry Division. Discharged in 1919, his U.S. citizenship was restored by Al Smith (Governor of New York).
Monk Eastman, leader of the Lower East Side gang the Eastmans, was shot to death on Christmas night, at 3:43 a.m., December 26th, 1920, at the SW corner of 14th Street and 4th Avenue in front of the subway station by the Bluebird Cafe at 62 East 14th Street. Monk was shot by Jerry Bohan, a Prohibition agent who was one of his partners in crime. His wartime pals paid for his military funeral and plot at the Cypress Hill Cemetery in Brooklyn.
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