Top 10 Biggest Gangsters and Mobsters of All Time

In the annals of crime, there are few figures more notorious than the gangsters and mobsters of yesteryear. From Al Capone to John Gotti, these infamous figures made headlines for their ruthless tactics and larger-than-life personalities. They were the subjects of countless films, books, and documentaries, and they continue to captivate the public imagination to this day.

But who were the biggest gangsters and mobsters of all time? This is a question that has long intrigued criminologists, historians, and true crime enthusiasts alike. Was it the legendary Scarface, who ruled over Chicago with an iron fist during the Prohibition era? Or perhaps it was Lucky Luciano, the mastermind behind the modern American Mafia?

There are plenty of candidates to choose from, each with their own sordid tales of violence, corruption, and betrayal. But the real question is: who do you think deserves to be at the top of this list?
The Top Ten
1 Al Capone Al Capone, also known as "Scarface," was a notorious American gangster who rose to infamy during the Prohibition era. He became the head of the Chicago Outfit, a crime syndicate that smuggled and sold illegal alcohol. Capone was involved in numerous criminal activities, including extortion, prostitution, and murder. He was eventually convicted of tax evasion and sentenced to 11 years in prison. Capone died in 1947 at the age of 48 from complications related to syphilis.

This man was literally the mayor of Chicago because he had complete control over a majority of the cops, the mayor, and scared or massacred all of the other gangsters. He was so good at getting away with things he got caught for tax evasion, not the dozens of murders he committed. He was the person who inspired Scarface. But still, the truth is he was just a sick human being.

This guy sure has had a lot of influence on people, especially in music and movies. Megadeth's song Public Enemy Number 1 is based solely on Al Capone. He was one bad guy, that's for sure.

2 Lucky Luciano Charlie "Lucky" Luciano was an Italian-American mobster who is considered one of the founders of the American Mafia. He is credited with creating the Commission, a governing body that oversaw all organized crime activities in the United States. Luciano was involved in various criminal activities, including bootlegging, gambling, and prostitution. He was sentenced to 30-50 years in prison in 1936 for running a prostitution ring, but his sentence was later commuted in exchange for his assistance during World War II. He was deported to Italy in 1946 and died there in 1962.

I cannot put into words how much bigger Luciano was compared to Capone. He did much more to shape the Mafia than Capone did. Capone was most famous for the St. Valentine's Day Massacre, in which he got the wrong guy, which ultimately forced the Feds to go after him, sending him to jail.

Also, Morello should be in this, either 2 or 3.

He was the Boss of all Bosses and had what you call a Team of gangsters, and everyone played their part flawlessly.

He was the Boss of all Bosses and formed the Commission. One tends to forget that he was even the Boss of Al Capone.

3 Carlo Gambino Carlo Gambino was an Italian-American mobster who is considered one of the most powerful bosses in American Mafia history. He became the head of the Gambino crime family in 1957, which was the largest and most powerful Mafia family in the United States at the time. Gambino was involved in various criminal activities, including extortion, loan-sharking, and murder. He died of natural causes in 1976 at the age of 74.

The power and influence this man had were incredible. When he was boss, nobody got away with anything. He took control of a small crime family and turned it into the biggest, richest, and most powerful Mafia family in the US.

4 Bugsy Siegel Bugsy Siegel was an American mobster who was involved in the development of the Las Vegas Strip. He was a prominent member of the Italian-American Mafia and was involved in bootlegging, gambling, and murder. He is also believed to have been involved in the founding of Murder, Inc., a group of contract killers. Siegel was assassinated in 1947.
5 Vincent Gigante Vincent Gigante was an Italian-American mobster who was boss of the Genovese crime family. He was known for his eccentric behavior, which included walking the streets in a bathrobe and mumbling to himself. He was involved in extortion, loan sharking, and murder. He was eventually convicted of racketeering and murder and died in prison in 2005.
6 John Gotti John Gotti, also known as "The Teflon Don," was an Italian-American mobster who became the boss of the Gambino crime family in 1985. Gotti was involved in various criminal activities, including racketeering, extortion, and murder. He gained widespread notoriety for his flamboyant personality and high-profile legal battles. Gotti was eventually sentenced to life in prison without parole in 1992 and died of throat cancer in 2002 while still incarcerated.

This man is the best. He had his own boss killed at the risk of getting killed himself. He was a man's man and didn't take anything off anybody. Rest in peace, John Gotti.

7 Pablo Escobar Pablo Escobar was a Colombian drug lord who controlled the MedellĂ­n Cartel, one of the most powerful drug-trafficking organizations in history. At the height of his power in the 1980s, he was responsible for the majority of cocaine smuggling into the United States. He was also responsible for numerous acts of violence, including bombings, assassinations, and kidnappings. Escobar was eventually killed by Colombian authorities in 1993 while on the run.

This man is the only one on this list who influenced countries.

8 Meyer Lansky Meyer Lansky, also known as the "Mob's Accountant," was a Jewish-American mobster who was involved in various criminal activities, including bootlegging, gambling, and money laundering. Lansky was a close associate of Lucky Luciano and helped him establish the Commission. He was also involved in the development of Las Vegas as a gambling destination. Lansky died of lung cancer in 1983 at the age of 80.
9 Joseph Bonanno Born in Sicily, Joseph Bonanno was an American crime boss who founded the Bonanno crime family in New York City. He was involved in racketeering, loan-sharking, and other criminal activities. He wrote an autobiography called "A Man of Honor."
10 Dawood Ibrahim Dawood Ibrahim is an Indian crime boss and the founder of the D-Company, which is one of the most powerful criminal organizations in South Asia. He has been involved in numerous illegal activities, including drug trafficking, extortion, and terrorism. Ibrahim is considered one of the most dangerous and influential mobsters in the world.

He is literally the founder of the D-Company, which is a name given by the Indian media to Mumbai underworld's organized crime syndicate, still controlled by him to date. To avoid being at risk by running Mumbai's organized crime while being in Mumbai itself, this individual fled to Pakistan for a safer environment to control the terrorist activities. As a matter of fact, he even has contacts within India's Bollywood, which is for sure one of the biggest industries in India.

He has organized various murders and even had a hand in the 26/11 attacks in Mumbai. To conclude, he is after all a total maniac, who is a top-tier terrorist, you could say.

The Contenders
11 Frank Costello Frank Costello, also known as "The Prime Minister of the Underworld," was an Italian-American mobster who was involved in various criminal activities, including bootlegging, gambling, and racketeering. He was a prominent member of the Luciano crime family, which later became the Genovese crime family. Costello was known for his political connections and was rumored to have had close ties to numerous politicians and public figures. He died of a heart attack in 1973 at the age of 82.

Frank Costello was the boss of the old Luciano family after Luciano was deported to Italy and a member of Luciano's first crew.

12 Albert Anastasia Albert Anastasia was an Italian-American mobster who was a founding member of the modern American Mafia. He was involved in racketeering, gambling, and murder. He was the boss of the Gambino crime family until he was assassinated in 1957.
13 Ronnie and Reggie Kray, "The Kray Twins" The Kray Twins were twin brothers who were notorious gangsters in London's East End during the 1950s and 1960s. They were involved in organized crime, including extortion, armed robbery, and murder. They were eventually arrested and sentenced to life in prison. Ronnie Kray died in prison in 1995, while Reggie was released on compassionate grounds in 2000 and died a few months later.

A pair of psychopaths, they didn't care who got in their way. They are the most notorious gangsters in British history.

14 John Dillinger John Dillinger was an American bank robber during the Great Depression. He was a notorious criminal who escaped from jail multiple times and was involved in several high-profile robberies. He was eventually killed by federal agents outside a movie theater in 1934.

He was a very bad gangster and bank robber who murdered lots of people during the Depression Era of the US, including a police officer. He escaped from jail twice.

15 Dutch Schultz Dutch Schultz was a New York City-based mobster who made his fortune through bootlegging during Prohibition. He was involved in a number of criminal activities, including extortion, gambling, and murder. He was eventually targeted by the government, and was killed in 1935.
16 Joaquin "El Chapo" Guzman Joaquin "El Chapo" Guzman is a Mexican drug lord and the former leader of the Sinaloa Cartel. He was considered one of the most powerful drug traffickers in the world and was responsible for the distribution of large amounts of cocaine, methamphetamine, and heroin. Guzman was known for his violent tactics and was considered a major threat to law enforcement.
17 James "Whitey" Bulger James "Whitey" Bulger was an American mobster who was a prominent figure in organized crime in Boston from the 1970s until his arrest in 2011. He was involved in extortion, money laundering, and murder. He spent 16 years as a fugitive before being captured and convicted of multiple crimes. He was killed in prison in 2018.

This guy ran Boston's criminal underworld for years and wasn't caught until he was 83. He even struck a deal with the FBI to ignore his crimes in exchange for information on the Italian Mob. He had everyone - the mobs, the FBI - under his thumb for years. Truly an icon of Irish mobs.

18 Spiros Velentzas Spiros Velentzas was a Greek-American mobster who was involved in organized crime in New York City during the 1980s and 1990s. He was known for his involvement in drug trafficking, gambling, and murder. He was eventually arrested and sentenced to life in prison.
19 Frank Lucas Frank Lucas was an American drug lord who operated in the 1960s and 1970s. He was responsible for the distribution of large amounts of heroin in the New York City area. Lucas was known for his innovative smuggling techniques, which involved transporting the drugs inside the coffins of dead American soldiers.
20 Amado Carrillo Fuentes Amado Carrillo Fuentes was a Mexican drug lord who was the head of the Juarez cartel. He was known as "The Lord of the Skies" because he used a fleet of planes to smuggle drugs across the border. He died in 1997 during plastic surgery to alter his appearance.
21 Mickey Featherstone Mickey Featherstone was a member of the Westies gang in New York City during the 1970s and 1980s. He was involved in a variety of criminal activities, including murder, extortion, and drug trafficking. Featherstone was known for his violent temper and was considered a ruthless and dangerous individual.

A former member of the Westies, he had a nasty reputation as a psychopath and was willing to kill anyone who dared challenge the Westies in cold blood. However, after being framed by his own boss and allies, he helped the police bring down the Westies and is now in the Witness Protection Program.

22 Raymond Washington Raymond Washington was the founder of the Crips gang in Los Angeles during the late 1960s. He was known for his violent tactics and was involved in a variety of criminal activities, including drug trafficking and extortion. Washington was considered a major threat to law enforcement and rival gangs.
23 Frank Matthews Frank Matthews was an American drug lord who operated in the 1970s. He was one of the biggest drug traffickers in the country, and his organization was responsible for the distribution of large amounts of heroin and cocaine. Matthews was known for his extravagant lifestyle and was considered one of the most elusive mobsters of his time.

At the same time as Frank Lucas and Nicky Barnes were fighting over Harlem, Frank Matthews was a major player and the major supplier of drugs in 21 to 25 states in the US.

24 Jimmy Coonan Jimmy Coonan was the leader of the Westies gang in New York City during the 1970s and 1980s. He was involved in a variety of criminal activities, including murder, extortion, and drug trafficking. Coonan was known for his violent temper and was considered a ruthless and dangerous individual.

He was the leader of the Westies, an Irish gang in Hell's Kitchen. Cold and murderous, he was a ruthless killer who would kill anyone, even members of his own gang. At one time, he hired a man named Billy Bokun to frame his own right-hand man, Mickey Featherstone.

However, Featherstone's wife, Sissy, proved his innocence, and the Westies went down.

25 Michael Franzese Michael Franzese is a former New York mobster and former caporegime of the Colombo crime family. He was born on May 27, 1951, in Brooklyn, New York. Franzese became involved in organized crime in the 1970s and eventually became a made member of the Colombo family. He is known for his involvement in a variety of illegal activities, including loan sharking, extortion, and racketeering. In 1986, Franzese was arrested and later convicted on racketeering charges. He served time in prison and became a born-again Christian while incarcerated. After his release from prison, Franzese turned his life around and became a motivational speaker, author, and consultant on fraud prevention and organized crime.
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