Herbie Sperling was one of the last real, old-style, tough Jewish hoodlums and a New York City heroin kingpin.
He was generally known to have a foul mouth and a bad attitude, and he wasn’t afraid to speak his mind. He also voiced his hatred of rats and stool pigeons. During his later years in prison, Sperling was even heard lamenting, “What happened to honor? As a kid, I was taught that being a tattletale was a bad thing.”
Herbert (Herbie) Sperling was a poverty-stricken Jewish kid born on December 29, 1938, in the gritty Hells Kitchen section of Midtown Manhattan’s far Westside. His parents were immigrant Jewish parents from Eastern Europe. By the time he was a teen, Sperling was said to have relocated down to the Little Italy area around the 6th and 4th wards, where he would reside and hang around the area’s Italian hoodlums for the rest of his days.
He had little supervision at home. His father, Irving, died when Herbie was only one year old, and his mother, Cecilia, didn’t have the wherewithal to properly raise and deal with him. It would soon lead him astray.
Sperling was always in trouble in school or on the streets with the cops. He was sent to a juvenile reformatory at the age of 13 for truancy. He banged around in his early years as a bar bouncer and even boxed as a featherweight.
By his mid-teens, he was already dealing heroin in Manhattan. In fact, in 1958, when he was only 19 years old, he was arrested in a major narcotics case along with Genovese Family soldier Joseph Valachi and other top mafia traffickers, including boss Vito Genovese. Young Sperling was thought to have been getting his drug supply from Valachi.
Herbie got married early to a girl named Josephine Chiaremonte. By the early 1970s, as he started earning better on the streets, he moved his wife and their three sons to the South Bellmore section of Nassau County. There, Sperling indulged himself in buying expensive cars, two luxury boats he docked by his home that he liked to cruise the waters of the Great South Bay in, and reportedly even an original Picasso painting.
Underworld lore has it that when he was a kid growing up, Vito Genovese had met and taken a liking to little Herbie. He was soon allegedly being utilized by older neighborhood racketeers to run numbers, carry a few packages of dope across town to various customers, and other similar tasks easily performed by a young, mob-star-struck kid. Hence, his later arrest with Genovese and his minions.
Often Imitated. Never Duplicated. Button Guys of The New York Mafia...There's Only One!
