Who was the most dangerous mob boss of all time?
Eternalized in many significant films like The Godfather or Goodfellas, mob bosses have long sparked the public’s curiosity.
But, behind these fictional characters were real bosses at the helm of vast and violent smuggling, drugs, money laundering, bootlegging, kidnapping, and murder operations.
Deeply hierarchical, wide-reaching, and tough to infiltrate, the heads of organized crime networks often reach beyond the state and function as law enforcement of sorts. As a result, mob bosses have almost always been notoriously untouchable.
We saw a big rise in the number of mob bosses during the illegal bootlegging days. The underworld in the past was much more dominant than in recent days. Bugsy Siegel and Al Capone are some of the most well-known top names of the most powerful mafia bosses of all time.
They’re known to the world for their involvement in drugs, smuggling, and sometimes murder cases. But they’re not the only ones you should know about. Let’s take a look at the 8 most powerful American mafia Dons.
Constantino Paul Castellano
(1915-1985)
“The Howard Hughes” of the Mob, “Big Paulie,” was born on June 26th, 1915. He was a crime boss following Carlo Gambino as head of the Gambino crime family.
Castellano took over illegal businesses, turning them into legitimate ones, and was taken as more of a businessman rather than a mobster.
He and his son Philip funded the Scara-Mix Concrete Club, a club with members that The Commission appointed to handle contracts that were anywhere between two million dollars and fifteen million dollars.
Paul built a 17-room mansion in Todt Hill on Staten Island designed to resemble the White House in Washington. It had an Olympic-size swimming pool, Carrara marble, and an English garden.
On March 30th, 1984, Castellano was charged with numerous felonies, including extortion, narcotics trafficking, theft, and the DeMeo murders. And he was arrested yet again on July 1st, 1985, for loan sharking and tax evasion, but he pleaded not guilty.
He passed away on December 16th, 1985, after being gunned down in front of a Steak House in the Manhattan area.
Al Capone
(1899-1947)
Earning the nickname Scarface, Alphonse Gabriel Capone was born in New York.
As a teenager, he was a Five Points Gang member before moving to Chicago to start a bootlegging business as co-founder of the Chicago Outfit, which later expanded to include smuggling and other illegal work. Besides his forms of extreme violence, he often bribed judges, police, and even the Mayor of Chicago.
Yet, after he allegedly publicly murdered seven rival gang members during the infamous Saint Valentine’s Day Massacre, he was declared Public Enemy No.1 by the city of Chicago.
He was eventually imprisoned, but not for what one might think. He ended up doing time for tax evasion but was later released. He passed away from a heart attack, leaving behind a $3 billion fortune.
John Gotti
(1940-2002)
“The Dapper Don,” called this way for his passion for fine suits and media coverage, Gotti became America’s most powerful mob boss during the 1980s.
Born in Queens, New York, Gotti was well-known for his careless temperament, which he displayed after ordering a hit on his Gambino crime boss, Paul Castellano, in ’85.
After this assassination, the Don took over and made millions in a myriad of illegal activities, including illegal gambling, loan sharking, and narcotics distribution.
Although he avoided prison multiple times throughout the 80s, earning the nickname “Teflon Don,” the FBI continued to pursue and build a case against him.
With the help of Gotti’s second in command, “Sammy the Bull,” Gotti was finally put behind bars in 1992 for several crimes, including five counts of murder, tax evasion, and racketeering. In 2002 he died of throat cancer while locked up in a Missouri federal prison.
Bugsy Siegel
(1906 – 1947)
Bugsy Siegel, one of the first big-name celebrity gangsters, was a Jewish-American mobster involved in murder, racketeering, and illegal gambling.
Siegel, who loved to gamble, changed it from being illegal into a legally profitable business and was also known for being a mafia enforcer and hitman. He also founded the Las Vegas Strip, where he and his guys robbed tourists for many years until his passing.
But that’s not all. His name also came up in many bootlegging cases with his close associate, Meyer Lansky.
In 1936, Bugsy moved to California, where he started building casinos for the East Coast’s mob bosses, started racketeering, and through this, favored many Hollywood celebrities and earned fame.
A hitman fatally shot Siegel on June 20th, 1947, at his girlfriend’s house in Beverly Hills.
Lucky Luciano
(1897 – 1962)
Known for being the first gangster to officially “legitimize” the mob’s power in the US, Charles “Lucky” Luciano began 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 sought to prevent any future gang wars.
However, Lucky’s luck ran out when he was convicted of illegally working girls. 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 was deported to Italy.
He spent his final years in Naples, where he eventually passed away due to a heart attack.
Frank Costello
(1891 – 1973)
Born in Italy and raised in East Harlem, Frank Costello began his criminal career at 13 years old. His association with Lucky Luciano in gambling and bootlegging gained his influence, and when Luciano went to prison, Costello became head of the Luciano crime family.
Nicknamed the Prime Minister, he used an Asian connection during the Vietnam War to traffic narcotics, virtually cutting off the Italian mob’s activities, which typically handled trade.
He survived an assassination attempt on his life that killed Albert Anastasia, escaped many legal cases brought against him, and ultimately died of a heart attack at age 82, leaving 52 million dollars behind.
It has been rumored that he was the inspiration for Mario Puzo’s book and Francis Ford Coppola’s film The Godfather.
Carlo Gambino
(1902 – 1976)
This was a crime boss who ruled the mob world for a long time and met his death… WITHOUT a bullet. Carlo Gambino was an Italian-American mafia member belonging to the Gambino crime family.
He earned several nicknames, including The Godfather, Don Carlo, The Dictator of NYC, and The King of the American Mafia. Gambino began his criminal journey at 19 when he was inducted as an assassin into the Cosa Nostra family in 1921.
Along with two other guys, Bugsy Siegel and Frank Costello, he joined a “Young Turks” gang that was led by Lucky Luciano. In 1957, Gambino requested the assassination of Albert Anastasia, which resulted in him becoming the head of the Mangano crime family.
He then changed the name Mangano to Gambino and took charge of loan sharking and illegal gambling. He ended up ruling as one of the most powerful mafias until his passing on October 15th, 1976.
Frank Lucas
(1930 – 2019)
Born in North Carolina, Frank Lucas eventually moved to New York’s Harlem.
Once there, under the mentorship of Harlem mob boss Bumpy Johnson, Frank would rise to become a powerful narcotics kingpin in the 60s and 70s, selling dope and cutting out the middleman by buying straight from his Asian suppliers.
By the 70s, Lucas was bringing in 1 million dollars per day from his “Blue Magic” and living large, which caught the eye of the FBI. After the police raided his New Jersey residence in 1975, he was convicted of drug charges and given a 70-year prison sentence.
After only serving five years, Lucas was set free due to his cooperation as a state witness on narcotics cases. He later stated that he was remorseful for his life of crime and the damage it did to his community. In May 2019, Lucas died of natural causes at the age of 88.
The 2007 film American Gangster, starring Denzel Washington, was based on his life.
One thing all of these mob bosses have in common is that their life is uncertain in most cases, and several gangsters met their end by being shot or serving time in prison for their deeds. Only a few died naturally.
If you enjoyed reading about all of these mob characters, we’ve got many more famous figures you can read about, including this one: Mary Tudor: 6 Shocking Things You Don’t Know About the FIRST Queen of England
