Top 20 Most Powerful Mafia Bosses of All Time

The rise in the number of mafia bosses began during the illegal bootlegging days of the Prohibition era. The crime world in the past was much more dominant, with several mafia bosses compared to the recent days.

Griselda Blanco, Pablo Escobar, Al Capone, and Bugsy Siegel are some of the top names of the most powerful mafia bosses of all time.

They happen to be known to the world for their involvement in drug cases, mob cases, smuggling cases, and sometimes in murder cases.

Let’s bring the 20 of the most powerful mafia bosses of all time who received the reputation for their criminal involvement.

20. Veto Genovese (1897- 1969)

A photo of American mobster Veto Genovese
A photo of American mobster Veto Genovese
Source: Wikimedia Common

Born on November 21, 1897, Vito Genovese was an Italian-born American mobster. He operated mainly in the United States and rose to power during Prohibition as an enforcer in the American Mafia.

Genovese was involved in the Castellammarese War, which helped shape the rise of the Mafia in the United States. 

He led Luciano’s crime family and was renamed as Genovese crime family in his honor and helped in the expansion of the heroin trade at an international level.

Genovese competed for the title of the boss of bosses by ordering the murder of Albert Anastasia and attempting the murder of Frank Costello. 

Then, he held a mafia summit to unite his power which the police raided. In 1959, Genovese was arrested for narcotics conspiracy charges and was sentenced to 15 years in prison.

In a high-stakes card game, Genovese and a mobster Ferdinan Boccia conspired to cheat a wealthy gambler for $150,000. Boccia demanded a share of $35,000 for introducing the victim to Genovese. 

Genevese decided to have him murdered instead of paying Boccia anything and killed him in a coffee shop in Brooklyn.

Luciano was sentenced to thirty to fifty years in prison on November 25, 1936, and Genovese became the acting boss of the Luciano crime family. In 1937, Genovese fled to Italy, fearing the prosecution for Boccia’s murder. Costello then became the interim boss.

Genovese bribed some fascist party members and became a friend of Galeazzo Ciano, the son-in-law of Benito Mussolini, and provided Ciano with cocaine.

When World War II ended, he donated almost 4 million dollars to Mussolini’s party and was awarded the Order of Saints Maurice and Lazarus. Genovese made a Commendatore after participating in helping create a new fascist party headquarters in Nola, Italy.

In September 1943, when enemies invaded Italy, he switched sides and offered to help the U.S. Army. He was appointed as the interpreter officer in the U.S. Army headquarters in Naples. 

Soon he became one of the Allied Military Government for Occupied Territories (AMGOT) most trusted employees. Genovese died at the United States Medical Center for Federal Prisoners, Missouri, after a heart attack on February 14, 1969.

19.  Paul Castellano (1915-1985)

A photo of American crime boss Paul Castellano
A photo of American crime boss Paul Castellano
Source: Wikimedia Common

Constantino Paul Castellano, also known as “The Howard Hughes” of the Mob and “Big Paulie,” was born on June 26, 1915. He was an American crime boss succeeding Carlo Gambino as head of the Gambino crime family.

In 1940, Castellano became a member of the Mangano family and became a capo underboss Vince Mangano’s successor, Albert Anastasia. After Anastasia’s homicide in 1957, Carlo Gambino was the boss. 

Castello attended an Apalachin meeting in Apalachin, New York, which the police raided, and Castellano was one of the sixty-one highest-ranking mobsters arrested.

He spent one year in prison on contempt charges for refusing to answer questions. He was then sentenced to five years in prison for conspiracy to withhold information in 1960.

Castellano was more a businessman than a gangster as he overtook non-legitimate businesses and turned them into legitimate ones. However, his business thrived from mob connections. 

He and his son Philip invested money in the Scara-Mix Concrete Club, a club of contractors selected by The Commission for handling contracts between two million dollars to fifteen million dollars.

He had his daughter’s boyfriend Vito Borelli murdered in 1975 as he heard Borelli compared him to Frank Perdue, the owner and commercial spokesman for Perdue Farms.

After the death of Carlo Gambino, Castellano was appointed to succeed him over his underboss Aniello “Neil” Dellacroce. Gambino believed that Castellano’s focus on white-collar business would benefit his crime family. 

Dellacroce was in charge of activities such as extortion, robbery, and loansharking.

Castellano ordered the murder of Nicholas Scibetta, a Gambino associate who was a cocaine and alcohol user and participated in public fights and insulted the daughter of Geroge DeCicco.

At the height of his power, Castellano built a 17-room mansion in Todt Hill on Staten Island designed to resemble the White House in Washington, D.C. 

It displayed Carrara marble, an Olympic-size swimming pool, and an English garden. He wore satin and silk dressing gowns and velvet slippers around the house instead of managing the business.

Castellano was charged for federal racketeering in the Gambino case on March 30, 1984, including Eppolito and DeMeo murders. Along with that, he was also accused of extortion, narcotics trafficking, theft, and prostitution. He was bailed for two million dollars.

Castellano was arrested for loan sharking and tax evasion on July 1, 1985, and pleaded not guilty.

On December 16, 1985, Castellano was shot several times with a hit team in front of the Sparks Steak House in Midtown Manhattan as he was exiting the car.

18.  Sam Giancana (1908- 1975)

 A photo of Sam Giancana
A photo of Sam Giancana
Source: Wikimedia Common

 American mobster Samuel Mooney Giancana was born in Chicago on May 24, 1908, to Italian immigrant parents. He has led the Chicago Outfit from 1957- 1966.

As a teenager, Giancana joined the 42 Gang, developing a reputation in organized crime. He was in control of the illegal gambling, illegal liquor distribution, and political rackets in Louisiana from the 1940s through the 1950s.

He joined the Chicago Outfit during the late 1930s. Giancana was involved in Chicago’s African-American lottery payout system for the Chicago Outfit in the early 1940s. He was the boss of the Chicago Outfit in 1975.

Giancana and the Mafia were involved in the victory of John F. Kennedy in the 1960 presidential election. He was recruited in 1960 by the Central Intelligence Agency (CIA) to assassinate the Cuban leader Fidel Castro.

Along with Mafia leaders Santo Trafficante Jr. and Carlos Marcello, Giancana was associated with Kennedy’s Assassination. He was also present at the Mafia’s 1957 Apalachin meeting held at the Upstate New York estate of Joseph Barbara.

In 1966, Giancaa fled to Mexico to avoid the grand jury questioning the arms smuggling to the Middle East for the Israeli Mossad via Panama. He was arrested in Mexico and was deported to the United States in 1974.

After his return, Giancana was scheduled t appear before the Church Committee, investigated by the CIA and Cosa Nostra collusion. He was shot in the head and neck seven times in his basement kitchen.

17.  Joe Masseria (1886- 1931)

A photo of Italian-American Mafia Boss Joe Masseria
A photo of Italian-American Mafia Boss Joe Masseria
Source: Wikimedia Common

 In a family of tailors, the early Italian- American Mafia boss in New York City, Giuseppe “Joe the Boss” Masseria, was born on January 17, 1886. He was the boss of the Genovese crime family from 1922- 1931.

Joe arrived in the United States in 1902 and joined the Morello crime family in Harlem. Masseria was arrested for burglary and received four to six years on May 23, 1913, for third-degree burglary.

Masseria and his boss Salvatore D’Aquila fought for power at the end of 1910 in New York City and were at war by the early 1920s. D’Aquila ordered his gunman Umberto Valenti to kill Masseria.

The boss of the Morello crime family, Vincenzo Terranova, was killed, and Valenti was responsible for this. Valenti also fatally wounded Morello’s underboss Silva Tagliagamba. Valenti and his men again attacked Masseria, the new boss of the rival Morello family.

Masseria fled away; however, the gunmen shot two women and four men on the street. Masseria tossed away his pistol, and the police arrested him while fleeing the scene.

Masseria was again attacked on August 9, 1922, as he walked out of his apartment. He ducked into a store, and the gunmen shot into the store from outside. Masseria survived this incident with two bullet holes through his straw hat that he was still wearing. 

This gained him new respect among gangsters as “the man who can dodge bullets.” His reputation started rising as D’Aquila began to fall.

Masseria was known as “Joe the Boss” as he became the head of the Morello family. He was chosen to replace D’Aquila as the new capo dei capi after D’Aquila’s murder. He then applied pressure on the other mafia gangs for financial tributes.

He called out Nicolo Schiro for committing a transgression and demanded ten thousand dollars to step down as the leader of his mafia crime family. This led to the Castellammarese War through 1930 and 1931.

He fought in the Castellammarese War in 1930 to take over the criminal activities in New York City. The war ended on April 15, 1931, with his murder by his lieutenant, Charles “Lucky” Luciano, in an agreement with his rival Salvatore Maranzano.

16. Joseph Colombo (1923- 1931)

A photo of American mobster Joseph Colombo
A photo of American mobster Joseph Colombo
Source: Wikimedia Common

 Joseph Anthony Colombo was born on June 16, 1923, in New York City. He was the boss of the Colombo crime family, one of the Five Families of the American Mafia in New York.

Columbus’s father was a member of the Profaci crime family. With the kidnapping of four high-ranking members of the Profaci crime family by Joe Gallo, the First Colombo War began in 1961. Gallo was arrested, and Joe Profaci, the family leader, died of cancer.

He created the Italian-American Civil Rights League in 1970. The first Italian Unity Day rally was held in Columbus Circle later that year. It was to protest the federal persecution of all Italians everywhere.

Colombo joined the Profaci family following his father and became one of the top enforcers and a capo.

After Profaci’s death, Magliocco assigned killing Lucchese and Gambino to one of his top hit men, Colombo. However, Colombo revealed the plan to his target. 

After Magliocco confessed his plan, the Commission spared his life but forced him to retire as Profaci’s family boss. He also had to pay fifty thousand dollars.

Colombo got rewarded by the Profaci family as a reward for turning his boss in. He was sentenced to thirty-day jail on May 9, 1966, for contempt by refusing to answer questions to the grand jury about his financial affairs.

The Italian-American Civil Rights League multiplied under the guidance of Colombo, and he appeared on television interviews, fundraisers, and speaking engagements for the League. 

He aligned the League with a rabbi and political activist, Meir Kahane’s Jewish Defense League, in 1971. This claimed the federal government harassed both groups.

With the assistance of Colombo and the League, Paramount Pictures started filming the movie, The Godfather in 1971. The film faced massive opposition from Italian-Americans to film in New York. 

However, the League fully cooperated after agreeing to remove the terms “Mafia” and “Cosa Nostra” from the film.

After a shooting, Colombo was paralyzed, and after two months, he could move his thumb and forefinger on his right hand. On May 22, 1978, Colombo died after an episode of cardiac arrest at St. Luke’s hospital in New York.

15. Dutch Schultz (1901- 1935)

A mugshot of American Mobster Dutch Schultz
A mugshot of American Mobster Dutch Schultz
Source: Wikimedia Common

 Born on August 6, 1901, Dutch Schultz was an American mobster based in New York City. During the 1920s and 1930s, he earned quite a fortune in organized crime-related activities such as bootlegging and the numbers racket.

His rackets were threatened by another mobster Lucky Luciano and were weakened by two tax evasion trials led by prosecutor Thomas Dewey. He asked the Commission’s permission to kill Dewey. 

After they refused, he disobeyed them and attempted to kill Dewy. For that, the Commission ordered his murder in 1935.

Flegenheimer worked at a nightclub owned by a small-time mobster and started robbing craps games and soon turned to burglary. He was caught breaking into an apartment and sent to prison. 

His mugshot at the age of eighteen was published in the book New York City Gangland in 2010.

After his release, Flegenheimer returned to Schultz Trucking and began smuggling liquor and beer into New York from Canada. This was the beginning of his association with criminals, and during his time, he became better known as “Dutch Schultz.” 

He went to work for Italian competitors after he left Schultz Trucking following a disagreement.

When Schultz worked as a bouncer at the hub social club in the 1920s, the owner Joey Noe, a gangster, was impressed by his cruelty and brutality when Schultz lost his temper. This led him to become a partner.

Schultz and Noe worked with John and Joe Rock, who ran a bootlegging operation in the Bronx. The younger brother Joe refused to buy beer from them. 

So, they kidnapped Joe, beat him, and hung him by his thumbs from a meat hook. They wrapped a bandage smeared with discharge from a gonorrhea infection over his eyes. 

After that, their gang met only a few oppositions, and they expanded across the entire Bronx and made them very wealthy.

Noe-Schultz operation flourished so much that they were the only gang to go against the Mafia’s Five Families. They got into a bootleg war with New York’s Irish Mob, led by Jack “Legs” Diamond

He also had to deal with conflicts within his gang when Vincent Coll, one of Schultz’s enforcers, demanded to become an equal partner. They received a flat salary instead of the customary percentage from the take.

To find new sources of income with the end of Prohibition, Dutch Schultz put his hand into the Otto “Abbadabba” Berman and the Harlem number rackets. Along with this, he started extorting New York restaurant owners and workers. 

He worked through a hulking gangster Jules Modgilewsky, also known as Julie Martin, and made deals with Waiters Local 16 and Cafeteria Workers Local 302 to extort money.

Before Schultz’s surgery for peritonitis, he got himself baptized and received the last rites from a Catholic priest. After a day, he died on October 24, 1935.

14.Vito Rizzuto (1946-2013)

A photo of Italian-Canadian crime boss  Vito Rizzuto
A photo of Italian-Canadian crime boss Vito Rizzuto
Source: Wikimedia Common

 Vito Rizzuto was born on February 21, 1946, and was an Italian-Canadian crime boss. He was also known as “Montreal’s Teflon Don” and was the leader of the Sicilian Mafia in Canada. He led the infamous Rizzuto crime family based in Montreal, Quebec.

He was born in Italy and immigrated to Montreal with his parents in 1954. Rizzuto’s father, Nicolo, married into a mob. He then started his crime organization in Montreal after taking over the Controni crime family.

Rizzuto was involved in the killing of three rival capos in 1981 in New York City. It was ordered by Joe Massino of the Bonanno crime family and was questioned by a Brooklyn federal grand jury for this. He was given a ten-year prison sentence in 2004 but was released in 2012.

Vito married Giovanna Cammalleri, the daughter of the mobster Leonardo Cammalleri. He also oversaw a criminal empire importing and distributing heroin, cocaine, and hashish in Canada. He laundered hundreds of millions of dollars and lent out millions through loansharking operations, and profited from illegal gambling, fraud, and contract killings.

He was arrested in 1972 for planning to commit arson of Renda’s hair salon. He was detained again in 1988 for plotting to import hashish to Canada.

Rizzuto was considered a soldier of the New York Bonanno crime family by the Federal Bureau of Investigation (FBI). He, however, was supposed to be the most powerful mob boss in the country by Canadian officials.

An arrest warrant was issued against Rizutto on February 11, 2005, for having connections with plans to launder money through Giuseppe Zappia in the construction of a multi-billion-dollar Strait of Messina Bridge connecting the Italian mainland with Sicily.

Rizzuto died on December 23, 2013, due to complications from pneumonia induced by lung cancer. At the age of 67. Rizzuto’s funeral was held at the Madonna della Difesa in Montreal’s Little Italy and was attended by around 800 people.

13. Frank Scalice (1893- 1957)

A photo of Italian-American mafia boss Frank Scalice
A photo of Italian-American mafia boss Frank Scalice
Source: Wikimedia Common

 Born on September 23, 1893, Frank Scalice was an Italian-American mobster active in New York City. He was also known as “Don Ciccio” and “Wacky” and led the future Gambino crime family from 1930 to 1931.

Scalice became the new boss of the family in 1930 after Mineo and his underboss, Stefano “Steve” Ferrigno, were murdered by Castellammarese Silicans led by Salvatore Maranzano. He became a firm friend and supporter of Maranzano in the Castellammarese War.

After the end of the war, Masseria was killed, and Mazaranzo organized the Five Families and a peace. However, Lucky Luciano forced Salice to resign as family boss after the murder of Maranzo in 1931 and was replaced by Vincent Mangano.

Scalice helped mobster Bugsy Seigel to open the Flamingo Hotel and Casino in 1945 in Las Vegas. He later was involved in the casino business.

After the death of Manganos, Anastasia became the boss of the family, and Scalice became the underboss.

Scalice was murdered by two gunmen on June 17, 1957, in the Bronx for selling memberships in the family to the high bidder.

12.Salvatore Riina (1930- 2017)

A mugshot of Italian mobster Salvatore Riina
Source: Wikimedia Common

 Salvatore Riina was an Italian mobster and chief of the Sicilian Mafia and was born on November 16, 1930. He was also known as Toto’ u Curtu and was famous for his ruthless murder campaign with assassinations of Antimafia.

Riina was the head of the Corleonesi criminal organization in the mid-1970s, succeeding Luciano Leggio. He achieved dominance through a campaign of violence, causing the police to target his rivals.

After the death of Michele Navarra, the head of the Mafia family in Corleone in 1958, Luciano Leggio became the new boss. Along with the three gunmen in Navarra’s murder- Riina, Calogero Bagarella and Bernardo Provenzano, Leggio increased the power of the Corleonesi.

They spent a few years hunting down and killing dozens of Navarra’s supporters and were forced to go into hiding to avoid arrest. Riina and Leggio in 1969 and tried for the earlier carried out murders but cleared of guilt by intimidating the jurors and the witnesses.

During the Second Mafia War, Riina and Leggio killed almost a thousand people as they wiped out their enemies along the way. Riina had mutually beneficial relationships with local political figures like the mayors of Palermo Vito Ciancimino and Salvatore Lima.

Riina ordered the murders of judges, police officers, and prosecutors to claim authority as the people in law enforcement questioned the existence of the Mafia.

Buscetta talked to the anti-Mafia judge Giovanni Falcone and became his informant. He revealed that the Mafia was a single organization led by a Commission and established that the highest Mafia members were involved in all the organization’s crimes. 

Four hundred seventy-five Mafia members were arrested, and three hundred thirty trees were convicted in the Maxi Trial.

To divert attention from the investigation, Riina ordered the murder of seventeen people and left two hundred sixty-seven wounded. This came to be known as the “Christmas Massacre.”

One day after his eighth-seventh birthday, Riina died on November 17, 2017, while in a medically induced coma after two operations in the prison unit of Maggiore Hospital in Parma.

11.Sonny Franzese (1917- 2020)

A mugshot of American mobster Sonny Franzese
A mugshot of American mobster Sonny Franzese
Source: Wikimedia Common

 John ”Sonny” Franzese Sr. was born on February 6, 1917. He was an Italian-born American mobster and was a longtime member and underboss of the Colombo crime family.

His career began in 1930 and revolved over eight decades. He was the underboss of the Colombo family until he was sentenced to fifty years in prison to organize a series of bank robberies.

Sonny became the underboss again in 2005 after he was paroled in 1978 and re-jailed six times on parole violations. He was again convicted of extortion in 2011 and was sentenced to eight years in prison.

When he was released on June 23, 2017, at the age of 100, he was the oldest federal prisoner in the United States. He was the only centenarian in federal custody.

He died on February 24, 2020, at the age of 103. 

10.Griselda Blanco (1943 – 2012)

Griselda Blanco - a Columbian drug lord of the Medellin Cartel
Griselda Blanco – a Columbian drug lord of the Medellin Cartel
Source: Wikimedia Common

The quote that only men are Mafia bosses is not necessarily accurate, and Griselda Blanco is the decisive proof. Griselda Blanco, who started with prostitution and pickpocketing, ended up booming the cocaine trade.

A Colombian drug lord controlled the Medellín Cartel and became a Miami-based cocaine drug trade pioneer. 

She was active in the underworld with several names, such as La Madrina, the Queen of Narco-Trafficking, the Black Widow, and the Cocaine Godmother during the 1980s through the early 2000s.

She was estimated in 200 murders while smuggling cocaine from Colombia to New York, Miami, and Southern California. Blanco, at her peak, was one of the richest women and the most powerful drug kingpins in the world.

She earned $80 million a month during the ’70s and ’80s and became the first-ever billionaire female criminal with a $2 Billion net worth as of 2012.

She married four men and bore four children. With the multi-billion dollar drug trafficking empire, she became one of the deadliest women of all time.

However, her mafia acts ended on the 3rd of September,2012, after police shot her dead.

9.Bugsy Siegel (1906 – 1947)

Benjamin Siegel is commonly known as Bugsy Siegel, a Jewish - American mobster
Benjamin Siegel is commonly known as Bugsy Siegel, a Jewish – American mobster.
Source: Wikimedia Common

Described as handsome and charismatic, Bugsy Siegel was one of the first front-page celebrity gangsters. He was a Jewish-American mob involved in the racket, murder, and illegal gambling. 

Siegel, initially known for being a mafia hitman and enforcer, became Murder, Inc. He loved gambling and turned illegal gambling into legal one during the Prohibition era.  

He also established the Las Vegas Strip, where he and his men robbed tourists for years until death. His name also came in several bootlegging affairs with his close associate, Meyer Lansky. 

In 1936, Siegel moved to California, started campaigning rackets, and built casinos out there for the mob bosses on the East Coast. He also favored many Hollywood celebrities and earned some fame for himself.

Siegel was shot dead by a hitman on the 20th of June, 1947, at his girlfriend’s house in Beverly Hills.

8.Pablo Escobar (1949 – 1993)

A mug shot of Pablo Escobar - a Columbian drug trader
A mug shot of Pablo Escobar – a Columbian drug trader
Source: Wikimedia Common

Pablo Escobar was a Colombian drug trader and famous narcoterrorist who founded the Medellín Cartel. He was known as The King of Cocaine, The King of Crack, El Padrino, and El Patrón.

He started his criminal journey around the 1970s by selling illegal cigarettes and fake lottery tickets, participating in motor vehicle theft, and kidnapping people for ransom.

With his experience working under other mafia bosses, he established his Cartel in 1976 and named it the Medellín Cartel. The cartel made their first smuggling routes to the United States to distribute cocaine, which eventually became the most successful cartel to supply in the US.

They would supply at least 70 to 80 tons of cocaine a day from Columbia. This made Escobar and his cartel one of the wealthiest in the world. His business, however, created the battle between rival cartels and resulted in killing police officers, locals, judges, and politicians.

Escobar also stepped into the 1982 Colombian parliamentary election and was elected as an alternate member of the Chamber of Representatives. He earned some fame by working on community projects for the construction of houses and football fields.

He was convicted of planning the Avianca Flight 203 and DAS Building bombings. In 1991, he surrendered to the police and was sentenced to imprisonment for five years. 

He escaped jail in 1992, and a nationwide manhunt was conducted. Escobar was shot dead by the Colombian National Police on December 2, 1993.

7.Albert Anastasia (1902 – 1957)

A portrait of an Italian-American crime boss, Albert Anastasia
A portrait of an Italian-American crime boss, Albert Anastasia
Source: Wikimedia Common

Italian origin, Albert Anastasia was one of the most ruthless and feared Italian -American crime bosses, mobsters, hitmen, and gangsters in American history.

He was well known as The Earthquake, The One-Man Army, Mad Hatter, and Lord High Executioner. He worked as a longshoreman when he came to the US and became a hitman and enforcer for Luciano.

Anastasia was appointed underboss and head of his Brooklyn rackets when Salvatore Maranzano and Joe Masseria were killed during the Castellammarese.

By 1951, Anastasia had transformed New York Harbor into a whole Crime zone. At the time, he served Vincent Mangano and continued for 20 years as an underboss. When Mangano was killed, he became the new boss of the Mangano crime family.

The conspiracy against Anastasia was aggressive for killing his boos, so Vito Genovese with Carlo Gambino planned on killing him. He was killed in a barbershop in Manhattan on the 25th of October, 1957.

6.Carlo Gambino (1902 – 1976)

A picture of Carlo Gambino, an Italian-American mafioso
A picture of Carlo Gambino, an Italian-American mafioso
Source: Wikimedia Common

If there was any crime boss who ruled the crime world for a long time and still met his death without a bullet, it was Carlo Gambino. Carlo Gambino was an Italian-American mafioso of the Gambino crime family.

He had earned several 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. 

Gambino carried out his criminal journey at 19 when he was inducted as an assassin into the Cosa Nostra in 1921. Along with two other fellows, Bugsy Siegel and Frank Costello, he joined a ‘Young Turks’ gang led by Lucky Luciano.

In 1957, Gambino ordered the assassination of Albert Anastasia and became the head of the Mangano crime family. He then changed the original name Mangano to Gambino family and took charge of loan sharking and illegal gambling.

He became the head of the Mangano crime family and renamed it the Gambino crime family after murdering Albert Anastasia in 1957

Gambino became more potent after the Apalachin Meeting in 1957 and the imprisonment of Vito Genovese in 1959. He controlled the Commission of the American Mafia until his death.

He finally met his end with a heart attack on his bed on October 15, 1976. In his criminal career of 50 years, he served only 22 months in jail for a tax evasion charge in 1937.

5.Frank Costello (1891 – 1973)

A picture of Frank Costello - an American mobster
A picture of Frank Costello – an American mobster
Source: Wikimedia Common

Frank Costello was introduced to the crime world by his brother, Edward, who was still a teenager. Frank was born in Cosenza, Italy, and grew up in East Harlem. He joined the local gang 104th Street Gang at the early age of 13 and started petty crimes.

He had already served in prison in 1908, 1912, and 1917 for assault and robbery. With Lucky Luciano, he was involved in gambling, bootlegging, and building operations in New York and the South in the 1920s.

The association of Luciano helped him to gain political influence on the local level. When Luciano went to jail for operating a prostitution ring in 1936, Costello became the head of the Luciano crime family, later changed to the Genovese crime family.

He had risen at the height of his criminal career and became an Italian-American Mafia gangster and crime boss. He gained his popularity through his nickname “The Prime Minister.”

In the 1950s, Costello faced several problems with the law as he was frequently taken in and out of jail for contempt and tax evasion by the US government. 

He had also developed a solid alliance with Albert Anastasia. However, in 1957, the assassination attempt was made upon them, in which Costello survived while Anastasia was killed. Vito Genovese, the rival New York mob boss, was behind this scheme.

Though he lost some dominance after the attack, he continued his operation. He eventually met his end with a heart attack on February 18, 1973.

4.Lucky Luciano (1897 – 1962)

Lucky Luciano - an Italian-American mobster
Lucky Luciano – an Italian-American mobster
Source: Wikimedia Common

Lucky Luciano was a great influencing mafia king in American history and the first gangster who legitimized mafia power in America.

Charles “Lucky” Luciano was also an Italian-born mob boss who started his crime by joining the Five Points gang. His power rose when he became the top assistant in Masseria’s criminal organization and after the Castellammarese War.

People also called him the father of modern organized crime in America due to establishing The Commission in 1931. Luciano was a mobster who had great ambition and business sense.

He proposed The Commission maintain his power over all the families and stop future gang wars. The other bosses appreciated his idea and approved it.

The modern Genovese crime family then received the first official heir, and it was Luciano. His dominance in the mafia world grew even further because of his contribution to the development of the National Crime Syndicate.

However, his fortune dropped when District Attorney Thomas E. Dewey, with his years of investigation, brought him to trial in 1936. Luciano was convicted for his prostitution rackets and sentenced to 30 to 50 years in jail.

Luciano, however, shortened his prison time as he had helped the US Navy’s security measures during World War II. Thus, he was brought to Italy from where he continued his drug business. He died from a heart attack when he was at Naples International Airport on January 26, 1962. 

3.John Gotti (1940 – 2002)

A picture of American mobster John Gotti
A picture of American mobster John Gotti
Source: Wikimedia Common

Apart from his criminal activities, John Gotti was famous for being called the “The Dapper Don.” His swagger and expensive suits always roamed around the media that made him a tabloid celebrity.

John Gotti was the American mobster and boss of the Gambino crime family in New York City. He began his criminal career at 12 when he started working for Carmine Fatico.

Even after joining the Gambino crime family, Gotti could not stop his heroin business, despite knowing that it was against the family ethics. His business of heroin was discovered by the Gambino family only in 1985, which led to chaos.

Gotti had to plan and organize the murder of Paul Castellano to save him and his business team. The murder of Paul led to him becoming the head of the Gambino family.

During the 1980s, Gotti was the most powerful crime boss in America, called the “Teflon Don.” He earned millions through criminal and illegal business, including loan sharking, prostitution, illegal gambling, and narcotics distribution.

He often avoided prison throughout the 1980s, but the Feds continued chasing him and built a strong case against him. Gotti was finally locked in jail in 1992 for several crimes involving five counts of murder, tax evasion, and racketeering.

Salvatore Gravano, who was Gotti’s underboss, helped the FBI to put Gotti behind the bar. Though Gotti was in jail, he continued his crime business through brother Peter and son Jr. He died of throat cancer in 2002

2.Frank Lucas (1930 – 2019)

A picture of an American drug smuggler, Frank Lucas
A picture of an American drug smuggler, Frank Lucas
Source: Wikimedia Common

Frank Lucas was an American drug smuggler trained under Harlem mob boss Bumpy Johnson from his teenage years. He worked for Johnson for 15 years.

He broke the monopoly that the Italian-American mob bosses had on the drug ring and developed his drug ring that became one of the most significant rings of the 20th century.

Lucas became a powerful drug lord in Harlem in the 1960s and 70s through his heroin trade. He cut out the middleman by contacting the direct suppliers in Southeast Asia to buy the drug.

By the 1970s, Lucas leveraged a lavish lifestyle with an earning of $1 million a day from his “Blue Magic” heroin. It caught the eye of authorities, and Lucas was convicted of drug charges after they raided his New Jersey house in 1975.

He was sentenced to 70-year prison in 1976, but he served only five years and was set free. Due to his cooperation on drug cases as a state witness, he could shorten his prison time. (rearrange)

Lucas boasted of smuggling the drugs in the US military aircraft during his high peak career after bribing the US army members. He eventually met his natural death on May 30, 2019.

Lucas has also been fictionalized in the movie The American Gangster (2007).

1. Al Capone (1899 – 1947)

Al Capone an American mafia
Al Capone an American mafia
Source: Wikimedia Common

Al Capone was an American mafia boss and businessman who established his crime empire through several criminal activities in the 1920s. During his criminal career, Capone was the most powerful and dangerous crime boss in the world.

Capone was also one of the wealthiest and most influential people in the world. By 1927, he became a billionaire, possessing a startling $3 billion net worth in 1929.

His criminal affair started when he became a member of the Five Points Gang as a teenager. He then became a bouncer in many organized crime premises in his early twenties. 

In his initial career, his mentor was Johnny Torrio, who helped him to grow in bootlegging. He, along with Torrio, co-founded and became the leader of Chicago Outfit, previously known as the Black Hand. Still, his fall and rise continued due to the North Side Gang.

Capone became the crime boss and expanded his crime empire through smuggling, bootlegging liquor, and prostitution after Torrio’s death.

He bribed police officials, judges, and the Mayor of Chicago, and his domination prevailed in the US. He also donated funds to several charity groups, which earned him the nickname “modern-day Robin Hood.”

He, however, was tagged as “Public Enemy No.1” when the Saint Valentine’s Day Massacre happened. In the event, he killed his seven gang rivals. It boiled the media and public to pressure the US government to put Capone behind the bar.

Thus, Capone’s organized crime reign ended when he was sent to jail after being found guilty on five counts of tax evasion in 1931. The imprisonment was decided for 11 years, but he was released in 1939 when he suffered an advanced case of syphilis.

Capone eventually died of a heart attack on January 25, 1947. At the height of his career, he received many names such as Scarface, Big Al, Big Boy, and Snorky.

Capone’s life has also been discussed in many books, articles, journals, and movies. The Untouchables (1987) was a blockbuster movie based on Capone’s life.

Conclusion

Mafia life is uncertain, and several gangsters met their end either being shot or serving the prison for their lifetime. Only a few died naturally. This piece has only included ten mafia leaders and misses several others, such as Tony Accardo, Whitey Bulger, Sam Giancana, etc. 

Anyway, who do you find the most powerful mafia boss enlisted in the article? Comment your thoughts below. 

5 thoughts on “Top 20 Most Powerful Mafia Bosses of All Time”

  1. Griselda didn’t get shot by the cops, she got gunned down in front of a meat market. Ironically she started the movement of killing Plp by motorcycle drive by n that’s how she got killed

    Reply
  2. Anastasia was definitely not killed by Carlo Gambino. I’m not debating that Gambino put the hit out, but he himself definitely did not murder Anastasia.

    Reply
    • Very true. Without the Mafia, we wouldn’t have Don Pendleton’s Executioner. Of course, only the first 38 were written by Pendleton, but check out the series. I have a hunch you will love it as much as I do. It’s only fictional, but fun.

      Reply

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