Edward “Monk” Eastman — Gangster of Gangsters

Born as Edward, “Monk” Eastman owned a pet store, became a boxer, served as a sheriff, and was also a bouncer. He was a gangster’s gangster for many years and was very well connected. He was one of the last of the New York gangsters of the late 1800s, running the streets before the Italian Mafia took hold.

His gang, the Eastman’s, engaged in many street battles with the Five Pointers  (from which Al Capone got his criminal start). The two were surely among the first to conduct drive-by shootings.

Eastman’s fall from grace, if that happens for gang leaders, occurred not long after the robbery of a wealthy young man. Eastman became a pariah with many of his political supporters in Tammany Hall, and was ultimately convicted and served most of a ten-year sentence. Upon release, Eastman failed at his attempted to regain control in the underworld. He settled on work as a burglar, pickpocket, and opium dealer.

Monk Eastman’s Mug Shot

In 1917, at the age of forty-three, Eastman enlisted in the New York National Guard under the alias William Delaney.   During his military physical, the doctor observed a lot of scars on Eastman’s body and asked which wars he had been in; Eastman replied that he had been in, “a lot of little wars around New York.” He served honorably in France during “the” World War (WWI), and the Governor of New York restoring his citizenship in full after the war.

Monk Eastman’s Military Funeral

Sadly, Monk did not change his ways and was murdered in 1921. He was buried, nonetheless, with full military honors.

Carter F. Smith, J.D., PhD, is a university professor and retired U.S. Army Criminal Investigations Division (CID) Command Special Agent. His book, Gangs and the Military: Gangsters, Bikers, and Terrorists with Military Training, published by Rowman and Littlefield, is available at bookstores everywhere, and the publisher’s site.

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