Monk Eastman

Edward "Monk" Eastman was a prominent American gangster in the late 19th and early 20th centuries. He founded and led the Eastman Gang in New York City. This group became one of the most powerful street gangs in the city during that era.

Eastman is often viewed as one of the last major gangsters of the 19th century. His era preceded the rise of the Jewish mob and organized groups like the Italian American Cosa Nostra. Because his criminal enterprise included many Jewish-American members, some historical reports labeled him as Jewish. However, researchers note he was likely a Protestant of British European descent. His family's religious ties were often linked to Baptist and Methodist traditions.

Eastman's early life began in the Corlear's Hook section of Manhattan's Lower East Side. He was born in 1875 to Samuel Eastman and Mary Parks. His father was a Civil War veteran who worked as a wallpaper-hanger. After his father left the family, Edward lived with his mother and his maternal grandfather, George Parks.

Parks worked in a dry goods store and helped Edward establish a pet shop on Broome Street. For many years, Eastman used the occupation of "bird seller" on official government forms. He was known for his love of pigeons and often kept them with him. This pet business provided a public cover for his involvement with neighborhood gangs.

As his reputation grew, Eastman's criminal activities became more organized. He worked as a bouncer, or "sheriff," at the New Irving Hall club. This position allowed him to meet influential politicians from Tammany Hall. These politicians were deeply involved in the ethnic immigrant communities of New York. They used Eastman and his followers for political purposes. The gang acted as "repeat voters" during elections. They also served as strong-arm men to intimidate political opposition. This relationship connected street crime directly to the city's political systems.

Eastman's career was defined by a violent rivalry with Paul Kelly. Kelly was the leader of the Italian Five Points Gang.

The two leaders fought for control of the city's underworld. This conflict reached a peak on September 17, 1903. A massive gun battle occurred on Rivington Street involving dozens of gangsters. The violence resulted in the death of Michael Donovan and the wounding of John Carroll. Many innocent civilians were also injured during the chaos. Following the battle, police arrested approximately 18 members of the Eastman gang.

To end the street warfare, Tammany Hall officials intervened in 1903. They organized a boxing match between Eastman and Kelly to settle the feud. The fight took place in an old barn located in the Bronx. It was an intense struggle that lasted for two hours. Both men received heavy punishment during the bout. Ultimately, the match ended in a draw. The politicians used this event to press the gang leaders to accept a truce. They wanted to stop the bad press and the danger to civilians.

Eastman's criminal dominance ended following a failed robbery in 1904. He attempted to rob a man on 42nd Street and Broadway. Pinkerton agents were watching the man and intervened during the crime. Eastman shot at the agents while trying to escape but was caught by police. Because of the bad publicity, Tammany Hall refused to help him. He was convicted of attempted assault and sentenced to ten years at Sing Sing penitentiary.

He served five years before being released in 1909. Upon his release, he found his gang had split into different factions. He lost his power and struggled with an addiction to opium.

In 1917, Eastman joined the United States Army during World War I. He served in France with the 106th Infantry Regiment, also known as "O'Ryan's Roughnecks." During his physical exam, a doctor noticed many scars from bullets and knives on his body. When asked about his history, Eastman joked that he had fought many "little wars" in New York.

After the war, he returned to petty crime and worked with a corrupt Prohibition agent named Jerry Bohan. On December 26, 1920, a dispute over money at the Bluebird Cafe led to a fatal shooting. Bohan shot Eastman several times, ending the gangster's life. Eastman was buried with full military honors in Cypress Hills Cemetery.