Having spent the last 45 years of his life behind bars, New York mob associate and heroin kingpin Herbie Sperling, one of the most powerful and prolific Jewish gangland figures in American history, recently died of natural causes in a federal prison hospital in Massachusetts. He was 79. Even today five decades following his reign, Sperling’s reputation is still formidable in certain east coast mob spheres. News of his death was important enough in the Big Apple to even be given an obituary write-up in The New York Times.

During his days on the street, Sperling maintained ties to the Genovese, Lucchese and Gambino mob crime families, as well as criminal factions within the African-American and Latino communities in Harlem. His inescapable place in mob lore comes as a result of being at the center of what became known as the French Connection heroin pipeline. A multi-millionaire by his mid-20s, he lived on a posh waterfront Long Island estate where he kept three yachts and a fleet of luxury automobiles prior to his incarceration.

Sperling was convicted of narcotics trafficking in 1973 and sentenced to life in prison. Born and raised in Hell’s Kitchen, he got his start in the underworld running errands for New York mafia Godfather Vito Genovese and Genovese soldier Joseph (Joe Cargo) Valachi in the 1950s. At 19, he was arrested with Valachi for heroin smuggling. Shortly thereafter, Valachi became the first person to testify to the existence of the mafia in the United States. Genovese himself went to prison — where he would die of cancer in 1969 — for a drug conspiracy.

Authorities suspected the small, foulmouthed, pugnacious Sperling of playing a role in at least two brutal slayings. In February 1972, Louie Mileto, a courier in his sprawling heroin network that stretched multiple continents, was found without a head or any limbs inside the trunk of his car in New York’s Hudson Valley after he was caught stealing (he had been beaten to death). While serving his life prison term, Sperling was indicted for paying fellow inmates to kill mobster and drug peddler Vincent Papa in the yard at a federal correctional facility in Atlanta in 1977, however was acquitted by a jury at trial.

Papa was informing on New York policemen who had helped him and Sperling steal back 400 pounds of heroin confiscated in the infamous 1962 French Connection bust, which took place out of the Bronx and was immortalized in the Oscar-winning eponymously-titled film starring Gene Hackman, Roy Scheider and Tony Lo Bianco a decade later. The $2,000,000 worth of heroin was ripped off from a NYPD evidence-storage locker in the months following the movie’s 1971 release to theatres.

Lo Bianco played a character inspired by Papa (affiliated with Lucchese crime family) named Sal Boca in the film. Sperling’s early mob mentor, Joe Valachi, got the Hollywood treatment too in the 1972 motion picture The Valachi Papers featuring action-movie icon Charles Bronson in the Valachi role and Italian actor Lino Ventura as Vito Genovese.

According to federal court documents, besides his heavy footprint in the international drug market, Sperling also had interests in gambling and loansharking rackets across the New York area in the 1960s and early 1970s. Once he got locked up, Sperling kept wheeling and dealing on the outside, often using his son Nicky as a liaison. The younger Sperling was nailed in a DEA sting when his dad’s prison buddy, notorious Harlem drug lord and black mob boss Leroy Barnes, turned state’s evidence and began informing in 1982.

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