10 of the Most Infamous Mob Bosses in History | History Hit

10 of the Most Infamous Mob Bosses in History

Immortalised in Hollywood films like The Godfather, mob bosses have long sparked the public’s imagination. However, behind these fictional depictions were real bosses at the helm of vast and violent smuggling, laundering, bootlegging, sex work, drug, kidnapping and murder operations.

Often deeply hierarchical, wide-reaching, and difficult to infiltrate, the arm of organised crime networks often reaches further than the state, and functions as a kind of quasi-law enforcement. As a result, gang mob bosses have almost always been notoriously untouchable. Here are ten of the most violent, prominent and feared mob bosses in history.

1. Al Capone (1899-1947)

Earning the nicknames Scarface, Big Al, Big Boy, and Snorky, Alphonse Gabriel Capone was born in New York. He was a Five Points Gang member as a teenager, before moving to Chicago to start a bootlegging business as co-founder of the Chicago Outfit, which later expanded to include smuggling and sex work.

Along with his methods of extreme violence, he often bribed police, judges and even the Mayor of Chicago. However, it was after he publicly murdered seven rival gang members during the infamous Saint Valentine’s Day Massacre that he was declared Public Enemy No.1 by the city of Chicago. He was eventually imprisoned for tax evasion but was later released. He died of a heart attack, leaving behind a whopping $3 billion fortune.

The life and times of perhaps the most infamous gangster in American history.
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2. Albert Anastasia (1902 – 1957)

Nicknamed The Earthquake, The One-Man Army, Mad Hatter, and Lord High Executioner, Umberto ‘Albert’ Anastasia was one of the founders of the modern American Mafia. Born in Italy, Anastasia began his career as a longshoreman in the US. He allied himself with the mafia, and co-founded and later became boss of the Murder, Inc. organisation, which allowed him to exercise control over New York’s entire shoreline. He later became boss of the Mangano crime family.

It was only after the notorious Castellammarese War, a bloody struggle for power amongst the Italian-American crime factions, that he was appointed leader of the modern Gambino crime family. He was eventually murdered in a barbershop, likely by members of the Genovese and Gambino families.

3. ‘Lucky’ Luciano (1897 – 1962)

Known for being the first gangster to ‘legitimise’ mafia power in America, Charles ‘Lucky’ Luciano started his life of crime in the Five Points gang, before becoming a top assistant in Masseria’s criminal organization after the Castellammarese War. He established the Commission in 1931, which formally connected the different mob families and aimed to prevent future gang wars.

Lucky’s luck ran out when he was convicted for sex work racketeering. However, his 30-50 year sentence was shortened after he cooperated with the US Navy during World War Two, then commuted on the condition he be deported to Italy. He later died of a heart attack in Naples.

4. Frank Costello (1891 – 1973)

Inspiration for ‘The Godfather’ Frank Costello, American mobster, testifying before the Kefauver Committee investigating organized crime, 1951.

Image Credit: Wikimedia Commons / Library of Congress. New York World-Telegram & Sun Collection.

Born in Italy but raised in East Harlem, Costello began his criminal career at the age of 13. His alliance with Lucky Luciano in bootlegging, gambling, and building operations gained him influence, and when Luciano went to prison, Costello became head of the Luciano (later Genovese) crime family. Nicknamed the Prime Minister, he used an East Asian connection during the Vietnam War to traffic heroin, effectively cutting off the activities of the Italian mob who usually controlled trade.

He survived an assassination attempt which killed Albert Anastasia, escaped many legal cases brought against him, and eventually died of a heart attack aged 82, leaving $52 million behind. It is said that he was the inspiration for Mario Puzo’s book and later Francis Ford Coppola’s film The Godfather.

5. Carlo Gambino (1902 – 1976)

Earning nicknames such as the Godfather, Don Carlo, the King of the United States Underworld, the Dictator of New York City and the King of the American Mafia, Carlo Gambino was head of the Mangano crime family, which he renamed the Gambino criminal family after he assassinated Albert Anastasia. After the Apalachin Meeting in 1957, he unexpectedly took control of the American Mafia Commission, and his power grew after Vito Genovese was imprisoned.

A discreet and secretive man, he died of a heart attack aged 74.

6. Paul Castellano (1915 – 1985)

A business-minded mob boss, Paul Castellano manoeuvred the Gambino crime family to its financial peak by driving the family away from illegitimate business like drug trafficking to safer practices like money laundering, extortion, construction and food.

He built a 17-room mansion on Staten Island to resemble the White House, and demanded a larger cut in mob profits, which, combined with resentment towards him being appointed the boss, led to him being gunned down outside a Manhattan restaurant aged 70.

7. Pablo Escobar (1949 – 1993)

Mugshot of Pablo Escobar, 1976.

Image Credit: Wikimedia Commons / Colombian National Police

As the most prominent capo of the eighties and nineties, Colombian narcoterrorist and drug trafficker Pablo Escobar is estimated to have murdered some 4,000 people. Known as the King of Cocaine, the King of Crack, El Padrino and El Patrónhe founded the Medellín Cartel, which, at its peak, supplied the US with 70-80 tons of cocaine per day, and caused crime in Colombia to skyrocket.

He was imprisoned in 1992, but escaped, with the ensuing nationwide manhunt eventually leading to him being shot and killed the day after his 44th birthday.

8. John Gotti (1940 – 2002)

With tabloids frequently picturing him in expensive suits, John Gotti was known as the Dapper Don. A criminal from the age of 12, Gotti murdered his boss Paul Castellano, which led to him becoming boss of the Gambino crime family. During the 1980s, he earned millions through loan sharking, sex work, illegal gambling and narcotics distribution.

He was eventually imprisoned in 1992 but continued his crime business from behind bars. He died of cancer in 2002.

9. Griselda Blanco (1943 – 2012)

Mugshot of Griselda Blanco, 1997.

Image Credit: Wikimedia Commons / Metro Dade Police Department

At her peak in the 70s and 80s, Griselda Blanco became the first-ever billionaire criminal, earning $80 million a month from the proceeds of smuggling cocaine from Colombia to the US. A drug lord of the Medellín Cartel, she was nicknamed La Madrina, the Black Widow, the Cocaine Godmother and the Queen of Narco-Trafficking.

Never one to carry out killings, she ordered the deaths of some 2,000 people. She was shot dead aged 69 outside a butchers by a man on a motorbike in Medellín, Colombia.

10. Frank Lucas (1930 – 2019)

A powerful drug kingpin in Harlem in the 60s and 70s, Frank Lucas broke the Italian-American mob boss drug ring monopoly. He sold heroin and cut out the middleman by buying directly from his suppliers in South East Asia. During his prime in the 1970s, Lucas was earning $1 million a day from his Blue Magic heroin, and boasted of bribing army members into smuggling the drugs via US military aircraft.

The police raided his New Jersey home in 1975, and he received a 70-year prison sentence. However, after just five years he was freed due to his cooperation in implicating others. He later expressed remorse over the damage that his life of crime did to the community, and died of natural causes in 2019.

Dan headed up to Birmingham to meet bestselling author and celebrity local historian Carl Chinn to learn the true history behind 19th century Birmingham's most notorious gang members: the Peaky Blinders.
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Lucy Davidson