Edward “Monk” Eastman, gangster, war hero

Edward “Monk” Eastman (1875 – December 26, 1920) was a New York City gangster who founded and led the Eastman Gang, which became one of the most powerful street gangs in New York City and is considered to be one of the last of the 19th-century New York gangsters. His father was a civil war veteran who abandoned the family by the time Edward was 5 and he lived with his maternal grandparents, mother and siblings.  

His first arrest was in 1898 and while in prison became part of the Allen Street Cadets. He was known for his messy hair and small derby hat as well as gold teeth.  His legitimate work included owning a pet store where he sold birds and as a bouncer for a local club. Eastman became acquainted with Tammany Hall politicians, who would eventually put him and his cohort to work as repeat voters and strong-arm men.

Eastman was sent to Sing Sing prison for 10 years after attempting to rob a young man who’s family had hired 2 Pinkerton guards to follow him. Eastman shot at the bodyguards and was caught by the police. Though Tammany Hall had helped him out multiple times in the past, they sat this one out, so Eastman had to do the prison time. He served 5 of the 10 years, but when he got out he found his gang fractured into many small divisions and one of his cohorts dead. With no gang to run with, he became a petty thief and opium addict. He served many small sentences in jail.

Eastman enlisted in the army for World War I and received many accommodations for bravery. He served in France with “O’Ryan’s Roughnecks”, the 106th Infantry Regiment of the 27th Infantry Division. After Eastman’s discharge in 1919, the Governor of New York, Al Smith, recognized his honorable service by restoring his U.S. citizenship (voting rights were removed with his conviction as a felon.). After returning from military duty, he returned to a life of petty crime and was shot on the street by corrupt Prohibition Agent Jerry Bohan.

Mr. Eastman was buried with full military honors in Cypress Hills Cemetery in Brooklyn, New York. Bohan was later convicted of his murder and served three years in prison.

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