Who was the real Tony Soprano?

“Hey, what’s this f–––––– thing, Sopranos? Is that supposed to be us?” Those words were spoken by Joseph ‘Tin Ear’ Sclafani, a soldier for the New Jersey-based DeCavalcante crime family. He had no clue that he was being recorded by an FBI informant at the time – and had been for a year.

Others would agree with Sclafani’s assessment of The Sopranos: there were definite similarities between the DeCavalcante family and Tony Soprano’s crew, part of the fictitious DiMeo crime family.

The new prequel film, The Many Saints of Newark, tells the origin story of Tony Soprano, but the real genesis of the character may be the DeCavalcantes’ capo ­turned-unofficial boss – and devoted family man – Vincent Palermo, long rumoured to be the real-life Tony Soprano. Still, David Chase’s Sopranos depicted mob life in New Jersey so realistically that several real gangsters could lay claim to inspiring the show.

Investigative reporter Greg B. Smith wrote about the DeCavalcante family in his book, Made Man. He noted one especially insightful likeness between reality and fiction: that the New Jersey mobsters had an inferiority complex, from being ridiculed by the New York Mafia families.

In real life, the New York mobsters called the DeCavalcantes “farmers”. In The Sopranos, New York boss Carmine Lupertazzi is similarly disparaging about the DiMeos. “Family? They're a glorified crew.”

The DeCavalcantes were formally recognised in the Sixties – then under the rule of founding godfather, Simone DeCavalcante AKA “Sam the Plumber” (named after his heating and air conditioning business).

It was thanks to DeCavalcante that Vincent Palermo would ultimately climb the ranks. Palermo married his niece, and DeCavalcante took a shine to him. Palermo – aka, Vinny Ocean (named for working at the fish market) – was also friendly with the Five Families of New York. On paper, Palermo was clean – totally unknown to the authorities. Greg B. Smith likened his resume to that of a “hardworking suburban dad”.

Simone DeCavalcante was put under the spotlight in 1969. The FBI had bugged his office for two years and released the transcripts – all was revealed, including his dalliances with a secretary. According to the transcripts, the Plumber was prone to Soprano-like anxiety dreams, though they sounded less cryptic. (“I had a terrible dream… about a bunch of cops!” he told his secretary.)

DeCavalcante pleaded guilty to a $20 million-per-year gambling racket and served two years. He ceded control of the family to Giovanni “John the Eagle” Riggi, who eventually ran the family from prison with an “acting boss” on the outside (much like the unseen, incarcerated boss of The Sopranos’ DiMeo family).

In 1989, Vincent Palermo got his chance to put the DeCavalcante family “back on the map” when celebrity mobster John Gotti – boss of the Gambino family in New York, and nicknamed “The Teflon Don” – called in a favour.

Fred Weiss, a newspaper editor-turned-schemer had got in way over his head with mob partners. Gotti believed that Weiss, facing a lengthy prison sentence for a toxic waste dumping scam, might flip and turn informant. Palermo was one of several men who carried out a hit on Weiss – killed by two gunshots to the face on September 11, 1989 – and was made a capo (captain of his own crew).

Later, the DeCavalcantes' acting boss, Giacomo “Jake” Amari, died of stomach cancer, causing a power struggle within the family – Palermo and another member plotted to have each other killed. Similarly, the DiMeos' acting boss, Jackie Aprile, dies of stomach cancer in the third season of The Sopranos, also creating a power struggle – ultimately won by Tony Soprano.

By 1998, one year before The Sopranos started on TV, Vinny Ocean had become de facto boss of the DeCavalcante family. That same year – by which time the power and reputation of the New York families had diminished – things unravelled, beginning with a literal daylight robbery at the World Trade Center. On January 14, 1998, three men hit a Brink’s van as it delivered cash for the Bank of America in the North Tower, getting away with bags containing $1.6 million. A DeCavalcante associate named Ralph Guarino planned the robbery. It was a daring heist; it was also a total farce.

Guarino had picked a trio of junkies to carry out the robbery. They unmasked mid-heist and showed their faces to some 55 hidden cameras. Their faces were quickly plastered across newspapers and TV bulletins and they were nicknamed “The Three Stooges” by the press. Most of the loot turned out to be foreign notes. Even worse, it emerged that they’d left behind bags containing $1.6 million of good old fashioned US notes.

Ralph Guarino ducked a 20-year sentence by turning informant on Vinny Ocean and his men. Indeed, it was via Ralph Guarino that the Feds listened in to Joseph ‘Tin Ear’ Sclafani questioning whether The Sopranos was based on their crew.

Greg B. Smith noted that The Sopranos borrowed some broader mob activities – such as calling card and airline ticket scams – but there are more specific details too. Both the real-life DeCavalcante and fictional DiMeo families hung out at pork stores (Sacco’s in real life, Satriale’s in the show); and both Vinny and Tony owned strip clubs (Vinny ran Wiggles in Queens, Tony runs Bada Bing).

There’s also the tale of John D'Amato, who was made acting DeCavalcante boss. D'Amato was whacked when it emerged that he’d had sexual relations with men at swinger clubs (“Nobody’s going to respect us if we have a gay homosexual boss sitting down discussing La Cosa Nostra business,” said one of his killers in a court testimony). His story is echoed in The Sopranos, when Vito Spatafore is revealed as gay and beaten to death.

Even a law enforcement agent close to the DeCavalcantes’ activities thought there might be a snitch among the DeCavalcantes, passing info back to the Sopranos team. “They’ve got to have somebody over there,” said the agent.

Unlike Tony Soprano, however, Vinny Ocean turned informant. Faced with hours of incriminating tapes, he cut a deal, admitted to his part in several murders, and entered witness protection. In 2009, the New York Daily News discovered his new life in Houston, Texas – running a strip club under a new name. “Strip club king and mob rat Vincent Palermo up to his old tricks,” said the report.

The Sopranos not only played homage to the gangster genre – packed with actors from other gangster films and various references – but also blurred a line that others might have warned shouldn’t be crossed. Real-life mob associates auditioned for parts. Famously, Tony Sirico, who plays Paulie Walnuts, was a known figure from the streets before he became an actor and warned David Chase not to make his character “a rat”.

Just before the show debuted, FBI surveillance observed Tony Sirico, Vincent Pastore – Big Pussy in the show – and Godfather star James Caan partying with Colombo crime family members at a New York restaurant.

The New Jersey mob were apparently pleased with the association. “It kind of gave them this almost romantic aura,” said Greg B. Smith on a documentary about the DeCavalcantes. “They were TV stars… they’d talk about it as if, ‘Of course they’d make a TV show about us.’”

It may have been a love-hate relationship with the series, however. Michael Imperioli – who played Christopher Moltisanti – had a nervy moment at his bar. A mystery drinker, still sat there at last orders, warned him: “I think you should know there’s some people in New Jersey who don’t like you very much and aren’t very happy with you.”

David Chase heard other feedback from mobsters, particularly about a scene in which Tony Soprano wore shorts at a barbecue. “A Don doesn’t wear shorts.” The line was worked into the show.

Chase took guidance from the FBI on how to keep the show realistic. He recalled hearing about the wiretapped conversation in which the DeCavalcantes pondered whether they were the real Sopranos. His reaction was quite simple: “Scared,” said Chase.

Others would disagree with Joseph ‘Tin Ear’ Sclafani. They’d argue that the real-life inspiration for The Sopranos wasn’t Vinny Ocean and Co, but the crew run by Ruggiero “Richie the Boot” Boiardo – and more specifically, his son, Tony Boy Boiardo – who ran New Jersey operations for New York’s Genovese crime family.

Richie started as a milkman before he began bookmaking and Prohibition-era booze-smuggling. So important was Richie’s flow of booze that a peace meeting between him and a rival smuggler was attended by Al Capone.

When Richie was released from a short prison sentence, he targeted the mobsters who’d taken over the Newark rackets in his absence – their bodies were soon found.

“The Boot” nickname is attributed to conflicting stories: because he was bootlegger; because he conducted business from a pay phone (with a Jersey-fied mispronunciation of phone booth – “in da boot”); or because he booted his victims to death. The flamboyant villain was once nicknamed “Diamond Richie” for wearing a $5,000 diamond-studded belt buckle.

Richie’s business spread from Newark to the Essex County suburbs, and he passed the reins to his son, Anthony Boiardo AKA Tony Boy in the late Fifties. On an FBI surveillance tape, Tony Boy boasted how the father and son duo had once beaten a “little Jew” to death: The Boot using a hammer, Tony Boy using a crowbar.

Like Sam the Plumber, the Boiardos made headlines in 1969. They were among 15 people indicted – also including Hugh Addonizio, the mayor of Newark, known as “the Pope” – for a construction racket: 64 counts of money laundering, extortion, tax fraud, and perjury.

Incredibly, Addonizio continued his campaign for a third term, but lost his seat and was sentenced to ten years. Tony Boy had a heart attack and escaped conviction.

Tony Boy, like Tony Soprano, saw a therapist. Years of living “the life” took their toll. There were other similarities: Tony Boy lived in Essex Fells, not far from Tony Soprano’s McMansion in North Caldwell; and like Tony Soprano, one of Tony Boy’s kids passed over the life to become a doctor.

Among the Boiardos’ men were the Russo brothers, John “Big Pussy” and Anthony “Little Pussy” (named for their skills as cat burglars) – who surely inspired The Sopranos’ Big Pussy Bonpensiero. Greg B. Smith's book, however, claims Anthony Russo for the DeCavalcante crew. Smith’s book is absolutely certain the DeCavalcantes are the true inspiration.

In an interview with Richard Linnett for Penthouse, Tony Boy’s son, Dr Richard Boiardo, said The Sopranos was “fundamentally” based on his family, though producers wouldn’t admit it. “Maybe they don’t want to get sued?” said Linnett. “Or whacked,” replied the doctor.

“Chase absolutely took material from the DeCavalcantes and other New Jersey and New York families for the show,” said Boiardo. “But it all started with my family… you could say that we’re the true OGs, the original gangsters. Of course, we weren’t as sexy as what you find now on TV and in the movies. The glamour was tempered with real heartache.”

In his old age, Richie the Boot believed he was the inspiration for The Godfather himself, Vito Corleone. On his grand estate in Livingston, he hung a sign in his vegetable garden that declared it “The Godfather Garden”. The bizarre, fortress-style estate was very much not a McMansion. One report described it as being in “the Transylvanian Tradition”. At the entrance was a statue of Richie the Boot on horseback, flanked by his children. Tony Boy died of a heart attack in 1978. Richie the Boot died in 1984, aged 93.

David Chase – who grew up in North Caldwell and heard stories about local crime – has been asked about the real-world inspiration for The Sopranos. Chase stated the show is “purely invention”, but has occasionally let slip potential influences. In a 2002 interview he said that while “90 per cent” is made up, it was “patterned” after the Genovese crime family, which included the Boiardo crew.

As the Cosa Nostra News blog suggested, maybe acknowledging the Boiardos is a legal technicality. After the show launched, a former municipal judge tried to sue Chase, claiming he’d given Chase ideas for the show – including stories about the DeCavalcante family – and hadn't been paid. Chase cited the Boiardo crew again in court. “The Mafiosi I had been most familiar with as a young man,” he said.

The DeCavalcante family has since been back in the spotlight. FBI agent Giovanni Rocco (an assumed name) published a book earlier this year, detailing how he had infiltrated the family. His undercover work led to numerous arrests in 2015, and Rocco was forced into hiding. The book is titled Giovanni's Ring: My Life Inside the Real Sopranos.

Similarities to both the DeCavalcantes and Boiardos are too striking and numerous to write off either family as the true inspiration. Perhaps it was the many sins of New Jersey that created Tony Soprano.