Criminal Career
In 1898 Monk Eastman was arrested and convicted under the alias William Murray (one of the many Irish monikers Eastman employed). He spent three months on Blackwell's Island for larceny. During this time, he belonged to a gang of pimps and thieves known as the Allen Street Cadets. Herbert Asbury reports that Eastman was known to have had a messy head of wild hair, wore a derby two sizes too small for his head, sported numerous gold-capped teeth, and often paraded around shirtless or in tatters, always accompanied by his cherished pigeons. In time, Monk's reputation as a tough guy (despite his squat five-foot-six inch frame) earned him the job of "sheriff" or bouncer at the New Irving Hall, a celebrated club on Broome Street, not far from his pet shop. At the New Irving Hall and Silver Dollar Smith's Saloon, Eastman became acquainted with the Tammany Hall politicians, who would eventually put him and his cohorts to work as repeat voters and strong-arm men.
Eastman's greatest rival was Paul Kelly, leader of the Five Points Gang. The warfare between these two gangs reached a fever pitch on September 17, 1903, with a protracted gun battle on Rivington Street involving dozens of gangsters. One man was killed and a second reported fatally wounded and numerous innocent civilians were injured. Members of the Eastman gang were arrested
Tammany Hall worked closely with both Kelly and Eastman. Its officials grew tired of the feuding and the bad press generated when civilians were killed or injured in the cross-fire. In 1903, Tammany Hall set-up a boxing match between Eastman and Kelly in an old barn up in the Bronx. The fight lasted two hours, with both men taking hard punishment before it was called a draw.
Monk Eastman lived at 221 E. 5th Street at the turn of the 19th/20th century, just about two blocks from Paul Kelly's New Brighton Social Club at 57 Great Jones Street.
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