The 20 Most Brutal Mob Bosses in History

The Mafia are an important element of Italian history and culture. These mobsters originate from Italy and the Italian island, Sicily. However, as the Italians emigrated to other locations across the world, mobs formed elsewhere. For example, Chicago and New York in the United States are two areas that are known to have Mafia groups running the criminal underworld. At the head of the mobs there is always a boss, also known as a Mafioso, a don, or a godfather. These are the men responsible running the mobs and they are also often responsible for ordering the murders of people. Some mobsters have gained notoriety for the level of brutality they have inflicted on other people and for the numbers of murders they have committed. Here are 20 of the most brutal mob bosses in history.

20. Bernardo Provenzano

Bernardo Provenzano is a member of the Cosa Nostra Sicilian Mafia who was born in Corleone, Sicily, on January 31, 1933. He earned himself the nicknames of ‘Binnie the Tractor’ and ‘The Accountant’. He first joined the Mafia in his teens and became close to some of the most legendary Sicilian mobsters of the 1950s. In 1958, he was one of the gunmen involved in the murder of Michele Navarra. A warrant for the arrest of Provenzano was issued in 1963 and he spent 43 years on the run, hiding in the homes of various associates. Despite being on the run, he became capo di tutti capi in 1993 following the imprisonment of Toto Riina. During his absence, he had already been found guilty of many murders, including those of Borsellino and Falcone, and had been sentenced to many life sentences. Once in prison, he was under constant video surveillance. He died from complications relating to bladder cancer in a prison hospital in Milan on July 13, 2016, at the age of 83.

19. Roy DeMeo

Roy DeMeo was a member of the Gambino crime family. This famous New York mobster headed the DeMeo crew. He was born in Brooklyn, New York, on September 7, 1942, and also went by names including Steven DiMare, Roy DiMare, and John Holland. Although the DeMeo crew were responsible for more than 100 deaths, it is believed that over 70 of these murders were committed by Roy DeMeo himself. In many cases, these victims were dismembered and disposed of in a manner that many were never found. The FBI were well aware of his criminal activities and was a person they were targeting. In 1983, DeMao went for a meeting with his men at the home of crew member Patty Testa. Just days later, his murdered body was found in the trunk of an abandoned car. He had suffered multiple gunshot wounds, including several to the head. Anthony Gaggi was suspected of his murder. However, there are also theories that he was killed by his own crew members while at the meeting at Testa’s house.

18. Giovanni Brusca

Giovanni Brusca was born in San Giuseppe Jato, Sicily, on February 20, 1957. He was a member of the Sicilian Mafia who was by the nicknames ‘The Pig’, ‘The Swine’, and ‘The Christian Slayer’. During his time in the Mafia, he claimed to have killed somewhere between 100 and 200 people but had lost count and was unsure of the exact number. When Riina was sent to prison, Brusca became one of the most powerful Mafia bosses in Sicily. It is believed that Brusca was involved in a series of bombings during the mid-1990s. It was also known to the authorities that Brusca was responsible for the deaths of many people. In his absence, he was found guilty of these crimes. He was finally arrested in 1996 and was sentenced to life in prison for his crimes. As he collaborated with the authorities, they have allowed him to spend one week out of every 45 out of prison to see his family.

17. Richard Kuklinski

Richard Kuklinski was a Polish-American contract killer who was born in Jersey City, New Jersey, on April 11, 1935. He was known as ‘The Iceman’ and ‘Big Rich’. Although he was associated with the DeCavalcante crime family of the American Mafia in New Jersey and the Five Families of New York City, he predominantly worked as a sole hitman. Officially, he was convicted of murdering six people. However, he has claimed he actually murdered over 100 people. He would often freeze his victim so the time of death was difficult to determine and this is what earned him the nickname ‘The Iceman’. In addition to the murders, he was also involved in pornography, money laundering, hijacking, arms dealing, and narcotics. He lived with his wife and children in New Jersey until he was arrested in 1986. His wife and family claim they were unaware of his criminal activities and that he was living a double life. Kulinski was sentenced to life sentences. He died in prison from Kawasaki disease in 2006 at the age of 70.

16. James Burke

James Burke is an Irish-American gangster who was part of the Lucchese crime family. He was born in New York City on July 5, 1931. He is the father of gangsters Frank James Burke and Jesse James Burke. One of his daughters, Catherine, married Anthony Indelicato who is a member of the Bonanno crime family. He also has another daughter, Robin. He is famous for his involvement in the Lufthansa heist of 1978 and the murders of those involved in the months that followed. Burke was the inspiration behind Jimmy ‘The Gent’ Conway, one of the main characters in ‘Goodfellas’ that was played by Robert De Niro. He was serving 20 years in New York State Prison when he died from lung cancer in 1996.

15. Vito Genovese

Vito Genovese was a mobster who rose to prominence during the Prohibition era. He was an enforcer who worked with Charles Luciano in the Castellammarese War. He played an important role in shaping the American Mafia and other aspects of organized crime in the United States. The Luciano crime family was later renamed the Genovese crime family and Vito Genovese led this for 12 years. Between 1957 and 1959, he was the Boss of all Bosses. During this time, he expanded the heroin trade to an International level. It is believed that Genevese is also responsible for the murder of mobster Ferdinand Boccia in 1934. In 1958, he was charged with crimes relating to narcotics and sentenced to 15 years in prison. Before going to prison, he had ordered the murder of mobster Anthony Carfano. Genovese died of a heart attack in 1969 while at the United States Medical Center for Federal Prisoners in Springfield, Missouri.

14. Anthony Accardo

Tony Accardo was also known as ‘Joe Batters’ or ‘Big Tuna’. He was born in Chicago, Illinois, on April 28, 1906. His career as a criminal spanned eight decades, beginning as a small-time hoodlum before becoming the boss of the Chicago Outfit in 1947. He was the final Outfit authority in 1972. Hide was involved in many different types of rackets and was particularly well-known as an enforcer. His violent streak was also well-known. When his house was burgled in 1978, the four thieves were later found with their throats cut. When Accardo retired, he lived with his daughter and son-in-law in Illinois. It was there that he died from heart and respiratory problems in 1992 at the age of 86. Despite his long criminal career and the horrendous crimes he had committed, he spent only one night in jail in his whole life.

13. Frank Costello

Francesco Castiglia became better-known as Frank Costello and was also referred to as ‘The Prime Minister’. He was born in Cassano Allo Ionio in Calabria, Italy, on January 26, 1891. During his criminal career, he rose to the top of the underworld crime scene in the United States and became an Italian-American Mafia gangster and crime boss. Eventually, he led the Luciano crime family, that was later known as the Genovese crime family. He ran a vast gambling empire and had significant political influence. He ordered a lot of deaths during his reign and this made him unpopular with many people. As a result, there was an assassination attempt on Costello in 1957. Costello died from a heart attack in his Manhattan home in February 1973.

12. Lucky Luciano

Charles ‘Lucky’ Luciano was born in Lercara Friddi, Sicily, on November 24, 1897. This famous Italian-American mobster and crime boss is considered the father of modern organized crime. Luciano was also the first boss of what is now the Genovese crime family and played an important role in the National Crime Syndicate. He ordered the murders of many people. In 1936, he was tried and convicted of running a prostitution racket. Although he received a 36-year prison sentence, he struck a deal and was deported to avoid imprisonment. He spent some time in Cuba and then lived in Italy. Although he was under police surveillance, he continued his criminal activities. Luciano died of a heart attack at Naples International Airport on January 26, 1962.

11. Matteo Messina Denaro

Matteo Messina Denaro is a Sicilian Mafia boss who is also known as Diabolik, which is the name of a comic book character. He was born in Castelvetrano in Sicily on April 26, 1962. Following Bernardo Provenzano’s arrest in 2006, Messina Denaro became known as one of the new leaders of the Cosa Nostra. Following the death of Salvatore Riina in 2017, he is now viewed as the boss of all bosses in the Italian Mafia. Messina Denaro has been a fugitive since 1993 and is one of the top ten most wanted men in the world. He has been linked to many deaths and his other criminal activities include protection rackets, narcotics, and corruption. His whereabouts are still unknown to the police although they have seized many of his assets.

10. Al Capone

Al Capone is probably the best-known mobster in popular culture and is often referred to simply as ‘Scarface’. This mobster, crime boss, and businessman was born on January 17, 1899, in Brooklyn, New York. He was the crime boss and co-founder of the Chicago Outfit and reigned for seven years until he was 33. He is particularly famous for leading the Valentine’s Day Massacre in which seven members of rival gangs were killed. In 1931, he was convicted of tax evasion and sentenced to 11 years in prison. While in jail, he began to show the symptoms of syphilitic dementia. Following his release from prison, he died after suffering a stroke that led to cardiac arrest on January 25, 1947.

9. Bugsy Siegel

Benjamin ‘Bugsy’ Siegel is a Jewish American mobster who was born in Brooklyn, New York, on February 28, 1906. During his time, he became something of a celebrity gangster and was instrumental in the development of the Las Vegas Strip. He was also hugely influential to the American Mafia, especially the National Crime Syndicate. Siegel was a bootlegger during the Prohibition and was one of the leaders and founders of Murder, Inc. He became particularly well-known for his use of guns and violence. Bugsy Siegel was tried for murdering mobster Harry Greenberg in 1939 but was later acquitted of the crime in 1942. On June 20, 1947, he was at the home of his girlfriend Virginia Hill in California when he was shot dead.

8. Arthur Simon Flegenheimer

Arthur Simon Flegenheimer went by the name of Dutch Schultz. He was born in New York City on August 6, 1901. He was a mob boss that led a crime gang that was the only non-Italian gang in the American Mafia. When Lucky Luciano was charged with tax evasion in 1935, he divided his empire and Schultz became one of the bosses. He was known for having a hot head and a violent temper. His undoing was putting a hit out on Thomas Dewey, the US Attorney for the Mafia Commission. After this, he was considered a liability and was shot dead in Newark, New Jersey, on October 24, 1935.

7. Carlo Don Carlo Gambino

Carlo Gambino was also known as Don Carlo or ‘The Godfather’. He was born in Palermo, Sicily, on August 24, 1902. He was inducted into the Cosa Nostra as an assassin in 1921 when he was just 19. Along with Bugsy Siegel and Frank Costello, he became a member of a gang called the ‘Young Turks’. This gang was headed by Lucky Luciano. Gambino then became a captain for the Mangano crime family and was given the responsibility of taking charge of loan sharking and illegal gambling. In 1957, Albert Anastasia was murdered and Don Carlo was put in charge of the Mangano crime family. Once he was the boss, he renamed it the Gambino crime family. He was the head of this family for 20 years. He died on October 15, 1976, in Massapequa, New York.

6. Frank Lucas

Frank Lucas was born in La Grange, North Carolina, on September 9, 1930. During his teens he befriended Bumpy Johnson, a gangster. When Johnson died, Lucas broke the monopoly that the Italian-American Mafia had on the drugs ring and established his own drugs ring, which became one of the biggest of the 20th century. He gained he privilege to smuggle heroin by bribing members of the US Army so he could use military aircraft. Both Lucas and members of his gang became well-known for their use of brutal violence in order to conduct their crimes. In 1975, he was jailed for drug trafficking that involved over 100 drug convictions. However, he struck a deal with the DEA. Although he had been sentenced to 70 years in prison, he was released in 1981 after serving just five years in prison.

5. John Gotti

John Gotti was born in The Bronx, New York, on October 27, 1940. He started working for Carmine Fatico at the age of just 12. Although he was a member of the Gambino crime family, he was selling heroin with his crew. That was a violation of the Gambino family rules and he was discovered in 1985. As he feared his actions would have repercussions, Gotti organized the murder of Paul Castellano so that he could take control of the Gambino crime family. His crimes finally caught up with him and he was arrested in 1992. He was convicted of racketeering, conspiracy to murder, laundering, and multiple murders. When he was sent to prison, it ended his reign as ‘The Teflon Don’. In 2002, he died of throat cancer.

4. Vito Rizzuto

It is not just Italy and the United States that have Mafia as Canada also has its own branch of the Sicilian Mafia. Vito Rizzuto is the alleged boss of this branch. He was bornin Cattolica Eraciea in Sicily on February 21, 1946, and moved to Montreal, Canada, with his parents in 1954. His father, Nicolo Rizzuto was a mobster for the Cotroni crime family. Vito Rizzuto followed in his father’s footsteps. Just some of his crimes include racketeering and loansharking. He was also involved in the murders of three of the captains of the Bonanno crime family. He was arrested in 2003 but was not jailed until 2012 for these crimes. Rizzuto died in Montreal Hospital at the age of 67 on December 23, 2013. His death was caused by complications related to lung cancer.

3. Vincent Louis Gigante

Vincent Gigante was also known by many other names, including ‘The Oddfather’, ‘The Robe’, ‘The Enigma in the Bathrobe’, ‘The Real Boss of New York’ and ‘Chin’. He was born in Manhattan, New York, on March 29, 1928. Unlike many other mobsters, Vincent Gigante was the first member of his family to have any involvement in the Mafia. He became a prodigy of the Genovese crime family during his teems before enjoying a short career as a light heavyweight boxer. He then went on to become a mob enforcer. Eventually, Gigante became the head of the Genovese crime family following the murder of Paul Castellano. This gave him the title of Capo di tutti Capi. Throughout his adult life, he endured a long battle with mental health issues. In 1997, he was convicted of multiple crimes, including racketeering and murder, and was sentenced to 10 years in prison. While in prison, his health began to decline. He died on December 10, 2005.

2. Nicodemo Domenico Scarfo

Nicodemo Scarfo was also known as ‘Little Nicky’, ‘The Killer’, and ‘Lethal Nicky’. He was born in Brooklyn, New York, on March 8, 1929. He was one of the Genovese crime family’s made men. By the early 1950s, he was given his own bookmaking operation. He later became the boss of the Philadelphia crime family. Those who knew him described him as cold-hearted and narcissistic. His downfall was trying to extort $1 million from Willard Rouse, a major commercial property developer. Rouse contacted the FBI, and this eventually led to the arrest of Scarfo. He was initially sentenced to 14 years for this extortion. However, he was then guilty of nine murders and the multiple attempted murder of Harry Riccobene. In total, he was sentenced to 45 years in jail. While serving time at Atlanta federal penitentiary, Scarfo died of natural causes on January 13, 2017.

1. Salvatore Toto Riina

Salvatore Riina is one of the most feared mob bosses of all-time. He was born in Corleone, Sicily, on November 16, 1930. He was born and raised in Sicily and this Italian mobster became the boss of the Sicilian Mafia. During his criminal career, he personally murdered at least 40 people and ordered hits on hundreds of others. He even ordered the murders of several anti-Mafia prosecutors. Unfortunately, it was this action that was his undoing that led to his arrest. He was charged with multiple crimes, including multiple murders, and was sentenced to life imprisonment. While in Parma Prison, he underwent two surgeries in the medical unit. Following this, he was in a medically induced coma. Just a day after his 87th birthday, he died on November 17, 2017. Even after his death, he is considered the most dangerous mob boss ever.


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