Edward Osterman grew up in the Williamsburg neighborhood of Brooklyn, New York. Noting Edward’s fondness for animals, his father set him up managing a pet store as a young man. However, Edward wanted more excitement in his life. He moved to Lower Manhattan to become a “sheriff,” a bouncer charged with keeping order at local nightclubs. Eastman succeeded at the job, gaining a reputation as a fearsome brawler. After a few years, he decided to quit his job as a sheriff and start his own gang. Monk Eastman’s gang grew to upwards of 1200 members and was financed by whorehouses, petty gambling rings, pick pocketing, and burglary.

Eastman’s chief rival was Paul Kelly, leader of the Five Points gang. Tammany Hall, New York’s infamously corrupt political machine, used both Eastman and Kelly to “get out the vote.” In return, Tammany Hall protected Eastman from prosecution. Eventually, Tammany Hall tired of Monk Eastman’s gang wars. Police arrested him following a gunfight with two Pinkerton’s agents, and he was sent to Sing Sing Prison for five years. Monk Eastman’s gang fractured during his absence, so when he returned, he survived as a petty criminal. When the U.S. entered World War I in 1917, the 44-year-old Eastman enlisted. He served honorably in France, and his full rights of citizenship were restored by New York Governor Al Smith in 1919. (As a convicted felon, Eastman had lost some of his rights of citizenship.) Unfortunately, Eastman resumed his life of crime, and was murdered by his partner in a bootlegging operation in 1920.

Artwork Information: Monk Eastman, 2008 Mixed Media Silkscreen on Paper 19" x 29"

Filed Under: Celebrity Arrests