Joe Bruno on the Mob — Monk Eastman

Monk Eastman was born Edward Osterman in 1875 in the Williamsburg section of Brooklyn. His father owned a restaurant, and to keep the young Osterman busy, his father bought him a pet shop. Osterman’s business venture failed, reportedly because he kept fighting with customers who wanted to purchase pets he had become especially fond of. He relocated to lower Manhattan and dived head first into a life of crime. He operated under several aliases, finally settling on the last name of Eastman.

The short and stocky Eastman was nicknamed “Monk,” because he resembled a monkey stalking the streets. He had an unkempt appearance and his pumpkin-sized head, with his frazzled hair, was covered by a derby two sizes too small. Eastman became known a a feared brawler, and was the bouncer at one of the roughest nightclubs on the Lower East Side, the New Irving Social Club on the Bowery. While he patrolled the club keeping the peace, he carried a four-foot stick, which he used to crack the heads of any patron who was not behaving properly. In just a few short months, Eastman had whacked the heads of forty nine near-do-wells, and not liking crooked numbers, he conked the skull of an innocent man, just to make it an even fifty. Eastman sent so many people to Bellevue Hospital, the hospital staff jokingly called their emergency room “The Eastman Pavilion.”

Yet Eastman apparently had a soft spot for women. If anyone of the female persuasion needed to be reckoned with, he reportedly dropped his stick, took off his brass knuckles and hit the woman just hard enough to give her a black eye. No hospital visit was necessary for the lucky young lady.

Eastman was also quite a willing killer; for hire, or just plain fun, especially when he was drunk, which was often. Eastman believed in “Dead Man’s Eyes,” which is the concept that when a person dies, the last thing that person he sees is permanent imprinted on the retina of their eyes. When Eastman killed someone, he truly believed he was leaving proof on the victim’s eyes that he was the shooter. So Eastman, being the cautious bloke that he was, after he killed someone, he shot out their eyes not to leave any incriminating evidence.

Eastman assembled a rough and tumble gang that reportedly numbered close to two thousand men. He curried favor with politicians by doing them “little favors,” like patrolling polling places during elections to make sure each voter cast their vote for the proper man. The politicians returned the favor by springing Eastman out of jail whenever an ambitious policeman decided to do something foolish, like actually arresting Eastman for one of his many crimes. But Eastman was so out-of-control with his thievery, thuggery and killings, he soon ran out of political favors.

In 1904, Eastman was finally sent to prison for beating and robbing a man uptown. He was sentenced to 10 years at Sing Sing Prison, but was released after serving only five. When he got back to his old haunting grounds, he found his gang was dismantled, and his former men working for other scattered ringleaders. Eastman was reduced to performing petty crimes in the streets for awhile, until he had the bright idea of joining the army. He wound up serving in France with the 106th Infantry Regiment of the 27th Infantry Division. He was honorably discharged in 1919 and immediately was back on the streets of the Lower East Side, causing his usual mayhem.

Eastman soon became involved with a crooked Prohibition agent named Jerry Bohan. On the night of December 26, 1920, the two men got into a drunken argument, and Bohan, knowing full well of Eastman’s reputation for killing easy, shot Eastman dead in front of 62 East Fourteenth Street.


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