The Inside Story Of The Real-Life New Jersey Mob Boss Who Inspired Tony Soprano

Published April 8, 2024
Updated April 9, 2024

Known as "Vinny Ocean," DeCavalcante crime family boss Vincent Palermo ruled northern New Jersey with an iron first, much like Tony Soprano.

The HBO series The Sopranos is widely acclaimed for its intricate character development, moral ambiguity, and incisive portrayal of American life. It tells the story of Tony Soprano, played by James Gandolfini, a New Jersey-based Italian-American mobster, struggling to manage the pressures of his criminal organization while trying to keep his family life intact. While the show is pure fiction, it takes clear inspiration from the stories of real mobsters, which raises the question: Who was the real Tony Soprano?

One of the most obvious candidates for the real Tony Soprano is Vincent Palermo, the one-time de facto boss of New Jersey’s DeCavalcante crime family, named the DiMeo family in the show. Like the fictional Tony Soprano, Vincent “Vinny Ocean” Palermo was not averse to using violent tactics to establish and maintain control, and like in The Sopranos, many members of his crew would later work with authorities to reduce their own prison sentences.

Vincent Vinny Ocean Palermo

NYPDVincent “Vinny Ocean” Palermo, the mob boss who inspired Tony Soprano, according to some.

But Tony Soprano and Vinny Palermo are not one-to-one reflections of each other. The Sopranos is not based on a true story and the lead character of David Chase’s famous television show was inspired by several infamous mobsters in order to tell the story of a complex figure within a dysfunctional family, trying to keep it all together.

This is the story of Vincent Palermo and the other real-life gangsters who helped inspire Tony Soprano and his crew.

How Vincent “Vinny Ocean” Palermo Inspired Tony Soprano

Vincent Palermo The Real Tony Soprano

RedditThe story of New Jersey mob boss Vincent Palermo mirrored that of TV kingpin Tony Soprano so closely that Palermo’s men were once caught on an FBI wiretap discussing The Sopranos.

To understand why many have cited Vincent Palermo as the inspiration for Tony Soprano, look no further than members of Palermo’s own crew. Soon after The Sopranos first aired and buzz around the series started to pick up, one member of Palermo’s crew said, not knowing it would be picked up by an FBI wiretap, “Is that supposed to be us? Every show you watch, more and more, you pick up somebody… There’s a pork store. Yeah, in Jersey, right? They got a topless joint over there. Jesus.”

Vincent Palermo had become the de facto head of the DeCavalcante crime family after marrying the niece of the man who started it all, Simone “Sam the Plumber” DeCavalcante. Unlike most other mobsters, Palermo had a clean record — police had no clue who he was.

Real Tony Soprano

HBOJames Gandolfini portrayed Tony Soprano on HBO’s The Sopranos, which ran from 1999 to 2007.

But in the late 1960s, the FBI honed in on DeCavalcante. The FBI bugged his office in 1967, and by 1969 they had released a series of transcripts that revealed the truth about his operations. Curiously, The Telegraph noted, DeCavalcante was prone to anxiety-driven dreams much like Tony Soprano.

Meanwhile, Vincent Palermo got his big break in the family in the late 1980s, when John Gotti asked him to take care of Fred Weiss, a former newspaper editor who had become entangled with the mob. He was facing a prison sentence, and Gotti worried that Weiss would ultimately give up information to police in exchange for a lesser sentence.

Palermo and a few associates killed Weiss, and the feat earned Palermo enough recognition that he was made a capo. A decade later, as The Sopranos was starting to come out, Vincent Palermo was in charge of the DeCavalcante crime family, and members of his family were hanging out at pork stores, just like the fictional DiMeo family, and operating a strip club, again similar to The Sopranos.

Who Inspired Tony Soprano

HBOThe Bada Bing! strip club run by Tony Soprano’s organization in The Sopranos, a similar arrangement to that of Vincent Palermo in real life.

But strip clubs, pork stores, and violent pasts aside, there is seemingly little else about Vincent Palermo that would make him the real Tony Soprano. After all, the show was never meant to be a retelling of Palermo’s life; it was an original story that drew inspiration from several real-life mob stories.

In fact, despite many online pointing to Vincent “Vinny Ocean” Palermo as the real Tony Soprano, there is one group of mobsters in particular that the show’s creator, David Chase, directly named as an inspiration: the Boiardo crew.

How The Sopranos Was Also “Patterned After” The Boiardo Crime Family

In a 2002 interview with New Jersey Monthly, David Chase explained that roughly “90 percent” of The Sopranos was fictional, but it was “patterned after” the Boiardo crime family.

Richard Boiardo

Newark Public Library / Internet ArchiveRichie “The Boot” Boiardo at his son’s funeral.

In fact, the show’s subsequent prequel film The Many Saints of Newark makes this connection clearer than ever, telling the story of a young Tony Soprano growing up in a tumultuous time when crime families were rising up against the DiMeos as he himself struggled to maintain control.

As the New York Post acknowledged in September 2021, the story has a lot in common with the real life story of Anthony “Tony Boy” Boiardo. While he did not suffer panic attacks like Tony Soprano, Anthony Boiardo suffered from anxiety-induced ulcers, and like his fictional counterpart, he began speaking with a psychiatrist to tackle his issues.

“Tony Boy worked with a therapist who had been a military doctor, specializing in PTSD,” Richard Linnett, author of In the Godfather Garden: The Long Life and Times of Richie “The Boot” Boiardo, told the Post. “Tony Boy was dealing with the stress of being the Boot’s son and running a mob family, which he was ill-equipped to do.”

Tony Boy Boiardo

Newark Public Library / Internet ArchiveAnthony “Tony Boy” Boiardo (bottom right) at a banquet at Vittorio Castle.

Boiardo’s father, Richie “The Boot,” had been the head of his family for decades by the time his son took over. They started to face hard times in the 1960s, but at their height, they had effectively owned Newark, controlling nearly all of the city’s underground operations.

The Boot was a cunning, shrewd, and murderous man. He even had his own “crematorium” at his expansive manor, a large fire pit where he’d burn “evidence” in the form of people who crossed him. His son Tony Boy, however, grew up in the lavish manor who lacked his father’s cleverness and rose through the ranks on pure nepotism, drawing the ire of other mobsters.

Many assumed that when The Boot died, it wouldn’t be long until someone killed Tony Boy.

Surprisingly, though, The Boot outlived his son. Tony Boy died after suffering a heart attack in 1978, at 64 years old. The Boot died of heart failure in 1984, at the age of 93.

It’s fairly easy to draw comparisons that’d mark Anthony Boiardo as the real Tony Soprano — especially when the show’s creator himself noted the connection. However, researchers familiar with New York’s crime families still debate to this day whether it was Vincent Palermo and the DeCavalcantes or the Boiardos who actually should actually earn the title of the “Real Sopranos.”

The True Stories That Inspired The Sopranos

One pivotal storyline on The Sopranos features the character Vito Spatafore, a member of the mob who is revealed to be gay and is ultimately beaten to death because of it. This plot was actually based on the real-life story of John D’Amato, who had been an acting boss for the DeCavalcante family.

When other mobsters, including Vincent Palermo, learned that D’Amato had been having sexual relations with men he met at swingers clubs, they killed him, claiming in court, “Nobody’s going to respect us if we have a gay homosexual boss sitting down discussing La Cosa Nostra business.”

Vito Spatafore In The Sopranos

HBOThe Sopranos‘ Vito Spatafore, played by Joseph Gannascoli.

This is another way in which the DeCavalcantes inspired The Sopranos, but other characters in the show seem to harken directly back to the Boiardos.

One of Tony Soprano’s children, for instance, opted to take a different path in life and become a doctor — just as one of Tony Boy Boiardo’s children had done. Meanwhile, two members of the Boiardo crew, John “Big Pussy” and Anthony “Little Pussy” Russo — named for their cat burglary skills — most certainly inspired The Sopranos’ Salvatore “Big Pussy” Bonpensiero.

In fact, Dr. Richard Boiardo — the son of Tony Boy — said in an interview with Richard Linnett that the show was “fundamentally” based on his family, even if producers won’t admit it.

“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.”

Real Story Of The Sopranos

Newark Public Library / Internet ArchiveJoe DiMaggio with Jerry Spatola and “Tony Boy” Boiardo standing behind him.

In the end, The Sopranos has a lot in common with the stories of both Vincent Palermo and the DeCavalcantes as well as the Boiardos, while also pulling inspiration from other mobster media that came before it. Was the “real” Tony Soprano actually Vincent “Vinny Ocean” Palermo? Or was it Anthony Boiardo who served as the main inspiration for The Sopranos?

Ultimately, the answer is both and neither. There are elements of both men’s lives in the character for sure, but Tony Soprano ultimately stands out as a distinctly fictional creation.

Besides, producers on the show could never admit to using either family’s story as inspiration, anyway — because then they’d have to give them a paycheck.

After learning about Vincent Palermo and the mobsters who inspired Tony Soprano and his crew, read the story of Tony Accardo, the elusive mobster who succeeded Al Capone. Then, learn about the most notorious Mafia bosses of all time.

Austin Harvey
A staff writer for All That's Interesting, Austin Harvey has also had work published with Discover Magazine, Giddy, and Lucid covering topics on mental health, sexual health, history, and sociology. He holds a Bachelor's degree from Point Park University.
John Kuroski
John Kuroski is the editorial director of All That's Interesting. He graduated from New York University with a degree in history, earning a place in the Phi Alpha Theta honor society for history students. An editor at All That's Interesting since 2015, his areas of interest include modern history and true crime.
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Harvey, Austin. "The Inside Story Of The Real-Life New Jersey Mob Boss Who Inspired Tony Soprano.", April 8, 2024, Accessed May 23, 2024.