20 of the Scariest Gangsters and Their Crimes

Jack Diamond

Jack Diamond was an Irish American gangster; commonly known as Gentlemen Jack or “Legs Diamond”, a bootlegger whose operations were primarily focused in Philadelphia during the Prohibition era. 

He had close friends who were also famous gangsters. Diamond oversaw bootleg alcohol sales in Manhattan. He also got involved in a series of kidnapping in Manhattan Diamond died in 1931, when enemies shot him.

Tom Devaney

New York-based mobster, Tom Devaney was the guy behind the drift between mobster Mickey Spillane and the Genovese crime family in the 60’s and 70’s. He led the gang war against James Coonan, an Irish-American mobster, and racketeer in Manhattan.

Devaney was killed in a bar-and-grill in Midtown Manhattan, he was shot in the head by a foe because Devaney was “interfering” with George Barone’s affairs.

James Coonan

This Irish-American mobster used to operate in New York, Manhattan as “Jimmy C”. He was introduced into crime when Mickey Spillane kidnapped his father. Coonan grew angry with Spillane and formed a powerful crew and overtook him.

Later, Coonan went on to commit several other crimes and faced charges of racketeering and weapon charges. He was sentenced to 75 years in prison without any possibility of parole.

Dawood Ibrahim

He is the man behind the infamous Indian organized crime syndicate dubbed as D-Company. Ibrahim currently heads a large, unlawful empire in India. He is on the wanted list of Interpol for cheating, criminal conspiracy and more. Ibrahim was number three on “The World’s 10 Most Wanted”.

He is believed to have masterminded, financed and organized the 1993 Bombay Bombings, a series of 13 bomb explosions in Mumbai. He used to have close relations to Osama Bin Laden of Al Qaeda and is currently the most wanted man in India.

Kray Brothers

Twin brothers, Ronald “Ronnie” Kray and Reginald “Reggie” Kray were English gangsters. These two were the foremost perpetrators of organized crime in the East End of London during the 50’s and 60’s. With their gang, the Krays were involved in armed robberies, arson, protection rackets, assaults, and murders. 

They were amongst the most feared gangsters of their time, becoming US celebrities in the 60’s. The Krays’ criminal activities remained hidden behind celebrity status and “legitimate” businesses. Ronnie died of a heart attack while in prison in 1995 and Reggie died of bladder cancer. Source: womensforum

Demetrius Flenory

Known as “Big Meech” in many cities around the America. Demetrius Flenory was among two of the Black Mafia Family founders. The Black Mafia Family was a large drug trafficking organization that primarily operated in Detroit, then expanded to other cities like Los Angeles and Atlanta.

He was convicted of trafficking cocaine throughout America for two decades and is currently incarcerated until 2032. Flenory is identified as one of the highest-earning traffickers grossing $100 million.

Joaquin Guzman

Joaquin Guzman (aka “El Chapo”) is a Mexican drug lord who heads the Sinaloa Cartel, a criminal organization named after the Mexican Pacific coast where it was formed. He became Mexico’s top drug kingpin in 2003 after the arrest of his revival Osiel Cardenas. 

Each year from 2009 to 2011, Forbes ranked Guzman as one of the most powerful people in the world. His net worth is about $1 billion.

James Burke

Burke, better known as “Jimmy the Gent”, an American gangster who is believed to have either committed or orchestrated the brutal murders of many of people. Burke is of Irish decent and head of the Lucchese Crime Family in the 1970’s. 

He is believed to have masterminded the Lufthansa heist, an extensive robbery that took place at the John F. Kennedy Airport.

Vito Genovese

He is an Italian-American mobster who reached the peak of his popularity during the Castellammarese War in the 30’s. Vito Genovese was known as the “Boss of all Bosses” and is deemed responsible for expanding the heroin trade to an international level. 

Genovese, like plenty of other mobsters, arranged to have people murdered. Karma came back to get him when he died in prison of a heart attack in 1969.

Meyer Lansky

Lansky was known as the “Mob’s Accountant” and was a major organized crime figure. He, along with many others, was instrumental in the development of the “National Crime Syndicate” in the United States. Lansky developed a gambling empire that reached across the world.

He was a member of the Jewish Mob, but undoubtedly had strong influence with the Italian Mafia and played a huge role in the consolidation of the criminal underworld. He died from lung cancer at his home in Miami Beach.

Jacques Mesrine

Lansky was known as the “Mob’s Accountant” and was a major organized crime figure. He, along with many others, was instrumental in the development of the “National Crime Syndicate” in the United States. Lansky developed a gambling empire that reached across the world.

He was a member of the Jewish Mob, but undoubtedly had strong influence with the Italian Mafia and played a huge role in the consolidation of the criminal underworld. He died from lung cancer at his home in Miami Beach.

James Whitey Bulger

The notorious Boston-based gangster, James Whitey Bulger, was a social bandit. He dedicated his life to leading protection racket which he organized himself. Their purpose was to chase after and kill drug lords and illegal gamblers. 

Bulger was indicted for 19 murders based on grand jury testimony from other former associates. In 2011, he was arrested for his involvement in a conspiracy to commit identity fraud. Bulger was also one of the FBI’s Top 10 Most Wanted Fugitives and is currently serving time with two life sentences.

Anthony Accardo

Nicknamed “Joe Batters” or “Big Tuna”, Anthony Accardo emerges from being a notorious hoodlum, to being the head of crime syndicate known for “The Chicago Outfit.” 

Accardo moved “The Outfit” into new operations and territories, greatly increasing its power and wealth. Accardo died from congestive heart failure.

Bugsy Siegel

This Jewish American mobster is known as one of the most infamous and feared gangsters of his day. Siegel was also a driving force behind the development of the Las Vegas Strip. 

In the 1940’s Siegel controlled and financed some of the original casinos in Las Vegas and became a bootlegger. He is the founder of Murder Incorporated and headed the Genovese crime family. Siegel was assassinated in Beverly Hills in 1947.

Carlo Gambino

Sicilian mobster, Don Carlo Gambino was the head of the Gambino crime family and leader of the American Mafia. He’s widely known for being low-key and very secretive. 

Gambino stood up against the Anastasia loyalists in the 60’s and expanded his rackets to several parts of the United States until he was able to control about 90% of the ports in New York. He died of heart disease in 1976 at his home in New York.

Frank Costello

Known as “The Prime Minister,” Frank Costello was a crime boss, Italian criminal and known as one of the most popular mob group leaders in America. When Costello was a young boy, his brother introduced him to gang activities.

By the age of 13, Costello had become a member of a local gang and started using the name, Frankie. He and others became involved in the operations of rum manufacturing. As Costello retired, he still retained power and influence in New York ‘s Mafia and remained busy throughout his final years. He died of a heart attack at the age of 82.

Billy The Kid

Known as Henry Antrim, a gangster who had his first murder victim at the age of 18. Antrim was a 19th-century gunman who became involved in the Lincoln County War. 

Throughout his life, he killed a little less than 30 people and stole several horses and cattle. Antrim died in New Mexico at the age of 21 from being shot.

Al Capone

Nicknamed “Scarface”, “Big Boy” and “Big Al”, Capone was an American gangster who dedicated his life smuggling liquor and involving himself in prostitution. He was involved with murders, bribery of government officials, robbery and bootlegging. 

People remember him as hospitable and generous, only turning evil when he felt crossed. He led a Prohibition-era crime syndicate and was brought behind bars on account of tax evasion charges. Before he died, he was diagnosed with late stages of syphilis that he contracted from a prostitute, which evidently led to cardiac arrest.

Griselda Blanco

Griselda Blanco is better known as, “The Cocaine Godmother”. Blanco was a pioneer of the biggest cocaine drug trade in Miami. She spent most of her childhood involved with criminal activity and had three sons. This little lady isn’t one to be messed with; rumor has it, she actually killed the majority of her husbands.

Blanco is also credited with inventing the motorcycle ride by killing, during her years controlling southern Florida’s fledgling cocaine trade. Blanco was killed in 2012 in a drive-by shooting.