Big Bosses: The Most Powerful And Notorious Mobsters In History

The origin of the American mob boss hails from Sicily, Italy, during the time of prohibition in the 1920s. During this time, organized crime families began to flourish in major cities such as Chicago and New York, particularly in “businesses” such as gambling, trafficking, bootlegging, and even loan sharking.

Throughout history, major players such as Al Capone, Frank Lucas, and Tony Accardo became known as some of the most notorious mob bosses, evading the law and building organized crime in their respective cities. During their time, these men lived anything but ordinary lives.

Lucky Luciano Is The Mastermind Behind Organized Crime

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Slim Aarons/Getty Images

Although Charles “Lucky” Luciano was born in Sicily, Italy, in 1897, he was raised in New York. During his time, the mobster played a role in creating the National Crime Syndicate and, thanks to his establishment of the governing body of the Commission in 1931, he is considered to be the mastermind behind modern-day organized crime in the United States.

As head of the Genovese crime family, Luciano became one of the most powerful mob bosses of the ’30s. It wasn’t until 1936 that the authorities were finally able to nail Luciano with illegal dealings.

Vito Genovese’s Enemy Became One Of The First Government Informants

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Born in a province in Naples, Italy, in 1897, Vito Genovese moved to Manhattan, New York, as a teen, quickly finding his appetite for money and power. But it was that greed that would compromise the entire mafia organization by the end of his reign. Before everything went downhill, though, he empowered the mob, helping Luciano build the Commission.

After Genovese “cleaned house” of his enemies, one of his associates, Joe Valachi, became intimidated, relaying mafia secrets to the government as their first-ever informant. Ultimately, in 1958, Genovese was sentenced to a Missouri prison for the distribution of narcotics. Eleven years later, he died of a heart attack.

Frank Lucas Claimed To Regret His Time As A Boss

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David Howells/Corbis via Getty Images

Born in 1930 in North Carolina, Frank Lucas made his way to Harlem, New York, eventually finding a mentor in “Bumpy” Johnson. Under his tutelage, Lucas rose in the ranks, becoming a powerful narcotic kingpin through the ’60s and ’70s. His strategy was successful because he cut out the use of a middleman, buying his supply straight from South East Asia.

His income of one million dollars per day gained the attention of the authorities. Lucas was arrested in 1975 and sentenced to 70 years in prison. Later, he claimed to feel remorse for living a life of crime. He died in 2019, at the age of 88, from natural causes.

Paul Castellano Was The Howard Hughes Of The Mob

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Known as the godfather of the Gambino crime family, the most powerful crime family in New York, Paul Castellano is what one would call a businessman, or “The Howard Hughes of the Mob,” as his nickname states. Born in 1915 in Brooklyn, New York, Castellano quickly learned the ways of the mob, climbing up the ranks and eventually becoming head of the family.

He was known for turning non-legitimate white-collar businesses into huge enterprises, using his people to infiltrate the food and construction side of things. Then, in 1985, he was slain by a testy John Gotti. Many blame Gotti for weakening the strong Gambino family, as the death was unauthorized.

Frank Costello

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While he was born in Cosenza, Italy, back in 1891, Frank Costello was raised in East Harlem, New York. Eventually, Costello moved up the ranks, becoming the head of the 104th Street Gang. During the ’20s, Costello was in close allegiance with Luciano, operating gambling rings, bootlegging, and building up their operations in New York as well as further down south.

Eventually, Costello became the syndicate boss after Luciano was arrested. But the law wasn’t far behind Costello, arresting him multiple times for contempt and tax evasion throughout the ’50s. Costello died at the age of 82, due to a heart attack.

John Gotti Was “The Dapper Don” Who Was Betrayed

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Yvonne Hemsey/ Getty Images

John Gotti, aka “The Dapper Don” for his love of dressing well, was one of the most powerful mob bosses in the United States during the 1980s. Born in 1940s New York, Gotti was known for his quick temper, a trait that was shown in 1985 when he ordered a hit on Paul Castellano, the Gambino crime boss.

After the hit, Gotti took over, making millions in organized criminal activity, including gambling, loan sharking, and the illegal distribution of narcotics. Authorities were finally able to put Gotti behind bars in 1992, with the help of his second-in-command Salvatore “Sammy the Bull” Gravano. In 2002, Gotti passed from throat cancer while serving in Missouri federal prison.

Authorities Never Found Meyer Lansky’s $300 Million

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Although he’s not a mob boss or the head of a major family, Meyer Lansky is probably one of the most financially successful gangsters in American history. Known as the “Mob’s Accountant,” Lansky helped his associate Lucky Luciano develop the National Crime Syndicate.

He also developed a worldwide gambling empire, something organized with the help of the Jewish mob. And while he had many ties with various families, Lansky was never arrested on anything but illegal gambling charges. In 1983, he died of lung cancer at the age of he was 80. At the time of his death, he was suspected to be worth $300 million! But the authorities never found the money.

Joe Bonanno Was One Of The Youngest-Ever Mob Bosses

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Anthony Calvacca/New York Post Archives /(c) NYP Holdings, Inc. via Getty Images

Born in 1905, Joe Bonanno, also known as Joe Bananas, was the Italian-American crime boss of the Bonanno family. It was one of the “Five Families” of New York from 1931 to 1968. Growing up in Sicily with a father involved in organized crime, it was almost as if Bonanno’s future was laid out before him.

By the time he was 26, Bonanno was one of the youngest-ever bosses of a major crime family. After a failed hit attempt, he fled to Canada, only returning to the United States years later. In 2002, Bonanno died of heart failure; he was 97 years old.

Al Capone Is Still Known For The 1929 Massacre

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In 1899, one of the most notorious mob bosses of the Chicago area was born, Al Capone. Joining the James Street Boys gang when he was growing up in New York, Capone eventually met his mentor Johnny Torrio. Together, they journeyed to Chicago.

Known for his use of extreme violence and the 1929 Saint Valentine’s Day Massacre of public executions, Capone became public enemy number one. Of course, the authorities couldn’t pin any of the slaughter on Capone, having to arrest him for tax evasion instead. He was sentenced to 11 years, only serving eight before dying of a heart attack in 1947.

Bugsy Siegel: The Hitman Who Became A Target

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Bugsy Siegel was born in Brooklyn, New York, in 1906. Known for being a mafia enforcer and hitman, Siegel was a close associate of boss Meyer Lansky. As such, the enforcer was involved in gambling, bootlegging, and eventually, the co-founding of the enforcement arm of the mob, called Murder, Inc.

In 1936, Siegel left New York behind moving to California to grow “businesses” out west for the east coast mob bosses. He began building casinos with his girlfriend, Virginia Hill. But the hitman became a target when Lansky learned he was pocketing mob money for his own gain. Siegel died in 1947, at the age of 41.

Tony Accardo Learned The Ways Of The Underground From Capone

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Tony Accardo is best-known for being the protege of Al Capone. Born in 1906 in Chicago, Accardo was taken under Capone’s wing, learning the ropes and climbing his way to the top ranks of the Chicago Crime Syndicate. By 1947, Accardo was the head of the Chicago Outfit.

Under his leadership, Accardo moved the mob toward more profitable business ventures, including call girl services and smuggling narcotics. While the authorities could never tie Accardo to his illegal dealings, they were able to indict him for tax evasion in 1960. The ruling was overruled. Eventually, he retired from the mob, and, in 1992, died from lung and heart complications.

John “Sonny” Franzese’s Son Testified Against Him

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Jeffrey Basinger/Newsday via Getty Images

Born in 1917, John “Sonny” Franzese had a criminal career spanning over three decades. Starting in the ’30s, Sonny worked his way up the ranks until he gained the title of underboss to the infamous Colombo crime family in 1963. A few years later, he was sentenced to 50 years in prison for a bank robbery.

But the most interesting part about Sonny’s life is that in 2011 when he was convicted for extortion. Sonny’s son, John Franzese Jr., testified against him, making him the first New York mobster to testify against their father and turn over state’s evidence. In 2020, Sonny passed away at the age of 103.

Sam Giancana Started A Life Of Crime At A Young Age

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Sam Giancana’s mob legacy is a bit more political than most on this list. Born in Chicago in 1908, Giancana took over the Outfit from 1957 to 1966, after Tony Accardo announced his retirement. His obsessiveness with American politics made him of interest to government leaders while his ruthlessness was the thing of legend in the underworld.

It’s said that before the age of 20, he’d committed no less than three murders and had been arrested over 70 times. After spending some time in prison after refusing to testify against mob activities, Giancana left the country. He should have stayed in South America; in 1975, he was assassinated in Illinois.

Carlo Gambino, The Original Godfather

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Italian-American crime boss Carlo Gambino, also known as The Godfather, was born in 1902, later becoming head of one of the “Five Families” of New York City, the Gambino crime family. Gambino ran the family for 20 years, a time in which he became the most dangerous and powerful mob boss in the country.

Ironically, the only time Gambino served time behind bars was in the ’30s, two years for running an illegal liquor still. And, while other families dabbled in narcotics, Gambino preferred “traditional businesses” such as loansharking, gambling, as well as hijacking and extortion. He died of heart disease in 1976.

Albert Anastasia Was A Ruthless Boss Known As The “Mad Hatter”

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During his time in the mafia, Albert Anastasia was a man of many traits. He was a crime boss of what became the Gambino family, a hitman, and an outright Italian-American mobster. Born in 1902, Anastasia went on to become one of the founders of what we know to be the modern-day American mafia.

He was also co-founder and boss of the mafia enforcement agency Murder, Inc. Anastasia is considered to be one of the most feared and ruthless leaders in all of mafia history, traits that earned him the nicknames of “Mad Hatter” and “The One-Man Army.” He ultimately died in a 1957 assassination.

Raymond Patriarca Sr. Ruled In New England For Three Decades

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Philip Preston/The Boston Globe via Getty Images

Raymond Patriarca Sr. was born in 1908, later becoming the long-time head of the Patriarca crime family. His control spread throughout the greater New England area for more than three decades, with each illegal business having to pay a kickback to the family.

It is said that Patriarca was a ruthless and brutal leader, once having allegedly ordered the murder of his own brother because he didn’t notice a recording device placed in his office. In 1970, he went on trial for murder conspiracy and was sentenced to 10 years in prison. But being the fearless leader he was, Patriarca continued to run the family from behind bars.

Lepke Buchalter Is The Only American Mob Boss To Get The Death Penalty

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Born in 1897, Lepke Buchalter moved up the ranks of the American mafia after being released from prison in 1922. From there, he and his friend Jacob “Gurrah” Shapiro began inflicting fear in New York’s garment industry union, slowly but surely gaining control of it.

Then, in the ’30s, Buchalter helped create what would later be known as Murder, Inc., the enforcement “agency” of the mafia. But his success came to a crashing halt when he was convicted of killing in 1941. His sentence was the death penalty by means of the electric chair at Sing Sing. He is the only American mob boss to be given a death sentence.

Dutch Schultz Went Against The Commission’s Orders

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Born in 1902, Dutch Schultz was an American mobster based in New York throughout the ’20s and ’30s. Like many mob affiliated people, Schultz made his fortune in crime-related organizations, including bootlegging and taking bets for the lottery. And while his “business” was going well, it didn’t stop him from being prosecuted by Thomas Dewey not once, but twice for tax evasion.

In an attempt to overturn his conviction, Schultz asked the mob’s governing body, the Commission, if they’d assassinate Dewey. They refused. And Shultz took the job upon himself, ultimately failing. Because he disobeyed the Commission’s orders, they set a hit on him. Schultz died in 1935.

Vito Rizzuto’s Family Was In A Power Struggle

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AFP via Getty Images

Born in Cattolica Eraclea, Sicily, Italy, in 1946, Vito Rizzuto immigrated to Montreal, Canada, with his family in 1954. His father, Nicolo, married into the mob and overtook the Cotroni crime family in the late ’70s. When he was old enough, Rizzuto took over as head of the family, becoming the alleged leader of the Sicilian mafia in Canada.

After pleading guilty to murder conspiracy and racketeering in 2007, Rizzuto was sentenced to ten years in prison. While behind bars, the Rizzuto family wound up in a power struggle, resulting in the death of his son and father. Rizzuto died from pneumonia in 2013, a result of lung cancer complications.

Stefano Magaddino Stashed $500K At His Legitimate Business

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Born in 1891, Stefano Magaddino became the longest-tenured boss in the history of the American mafia. As head of the Buffalo crime family, it’s interesting to point out that Magaddino actually owned and operated a legitimate funeral parlor, but made his fortune bootlegging and smuggling wines and spirits across Niagara River and into New York State.

For fifty years, Magaddino, known as “Don Stefano” to friends and “The Undertaker” to everyone else, was a dominant presence in the underworld of Buffalo, New York. His reign began to crumble in 1968 when the authorities found $500,000 stored away in his funeral home as well as his son’s attic.