10. Joseph Kennedy ($200-400 million, a billionaire figuring in today’s inflation)
Joseph Kennedy was the harmless-looking patriarch of one of the most powerful families in America, a corporate big shot… and strongly connected to the bootleggers who made millions selling alcohol during the Prohibition Era — if not a bootlegger himself. He is widely thought to have had dealings with Frank Costello, the head of the Luciano crime family, to facilitate smuggling alcohol into the country for easy distribution during the post-WWI period. Not only did Kennedy make a profit on his river of illicit booze, but he was also credibly accused of framing one of his rivals for rape in order to acquire his business (not to mention of being a gross anti-Semite and a major supporter of Hitler). Still, with his fortune measuring in the billions in today’s money (in 1957 he was named one of America’s richest people by Fortune magazine) it probably wouldn’t have been wise for the rest of the Kennedys to have disowned him completely…
9. Meyer Lansky ($300-400 million)
8. Griselda Blanco, “The Godmother” ($500 million)
The Miami-based “Godmother,” Griselda Blanco was arguably the most ruthless gangster working in the drug trade in the ’70s and ’80s. She was known equally for her good business sense as she was for her sociopathic tendencies (at the age of 11 she took a fellow child hostage, demanded a ransom and eventually killed him with a bullet to the head). Nothing like learning your job skills early in life… Blanco was also suspected of murdering her three husbands, ordering more than 200 hits during her time as a mob boss, and forcing men to have sex with her at gunpoint. She went into hiding in the mid-2000s and was last seen in 2007. If she is still alive, she is believed to be one of the wealthiest self-made women on the planet… If the glass ceiling was going to crack, why did it have to be here?
7. Anthony Salerno ($600 million)
The real life “Fat Tony” wasn’t nearly as cuddly as his Simpsons counterpart. Easily distinguishable by his trademark cigar and fedora, Anthony Salerno worked his way up to Consigliere of the Genovese family in the 1970s, having spent the previous few decades practicing his skills in illegal gambling, loan sharking and protection rackets. In the ’60s, his New York numbers empire was generating $50 million annually. Salerno was also notable for sending his close personal friends Christmas cards with pictures of himself in pyjamas on the front. Come to think of it, that is pretty cuddly… Nevertheless, he died at the age of 80, having spent the fading years of his life in jail.
6. Joaquín Loera ($1 billion)
Mexican criminal Joaquín Loera is a dark horse compared to more flamboyant drug dealers like Pablo Escobar, but that doesn’t make him any less influential. On the contrary. Loera, who made most of his billion dollars selling drugs from Mexico — and goes by a number of nicknames, including El Chapo and Crystal King — is currently a fugitive in his own country but is believed to be the most powerful drug dealer on Earth — meaning that the reported figure for his wealth could be a big under-estimate (he might be worth closer to $5 billion). The man who was listed as the the 937th richest man in the world by Forbes in 2010 was last heard from leaving a taunting message for the police near the bullet-riddled corpses of two military officers: “You’ll never get ‘El Chapo’, not the priests, not the government.” Well, he’s gotten away with it so far.
5. Al Capone (nearly $1.3 billion per year in income, allowing for inflation)
Iconic gangster Al Capone was practically the Bill Gates of the criminal world in his heyday. Capone supplied America with a river of bootleged alcohol in the 1920s and 1930s, and was frankly the real “untouchable” in Chicago. His iron-fisted (although certainly not iron-chinned!) rule over his city netted him a substantial income. Although there are no exact figures, it is estimated that in 1929 his criminal activities brought in more than $100,000,000 per year, over a billion dollars in today’s money. The cigar-chomping one even found the time to be a noted philanthropist and public figure… All that before he was brought down on tax evasion charges and syphilis. What a way to go for Chicago’s Godfather.
4. Susumu Ishii ($1.5 billion)
Scary tattooed Yakuza Godfather Susumu Ishii was a member of a manned suicide torpedo unit during World War II. However, after making it through the war alive, he fought his way into a new position as a gangster (sadly, one of the only jobs with long-term prospects as bad as his previous one) and worked his way up the career ladder in the Inagawa-kai gang. He made his estimated billion-and-a-half dollars primarily through loans, banking deals and real estate scams, but lost most of it when Japan’s bubble economy burst at the end of the 1980s. The gangster was so popular that when he died in 1991, his funeral was attended by over 5,000 people. How many bosses, mob or not, can say that?
3. Carlos Enrique Lehder Rivas ($2.7 billion)
Carlos Lehder was one of the co-founders of the infamous Medellín cartel, the group of South America-based drug barons who at their peak were responsible for shipping $60 million of illegal substances per day (and another of whose leaders, José Gonzalo Rodríguez Gacha, made Forbes‘ annual list of billionaires, in 1988). Described as a megalomaniac, this criminal spared no expense on the transportation of his precious cocaine, even buying a private plane and a Bahamian island to help him smuggle the substance into the US. How many legitimate businessmen could afford that? After amassing a fortune that would make ‘Scarface’ blush, he was eventually imprisoned in the 1980s and is still in jail in the US to this day. Hmm, on second thought, maybe crime doesn’t pay after all…
2. Pablo Escobar ($9-25 billion)
From being born in a village in Columbia with no electricity, Pablo Escobar worked his way up to become one of the wealthiest and most powerful men in the world. Now that’s a self-made man. At the peak of their operations, he and his associates in the Medellín cartel smuggled around 15 tons of cocaine every day, and protected their shipments by offering snooping officials “lead or silver” — lead for bullets or silver for a bribe. In 1989, Forbes magazine estimated that he was the world’s seventh richest man, with assets of close to $25 billion, and control of 80 percent of the global cocaine market. Despite being a ruthless, murderous drug lord, Escobar was also a compassionate family man (he once reportedly burned $1 million in cash to keep his daughter warm while on the run) but that doesn’t make his illegal exploits any less ominous.
1. Amado Carrillo Fuentes (around $25 billion)
Hans Gruber lookalike and cocaine baron Amado Fuentes was practically a real life James Bond villain. He had the whole package: a vast, drug-based Mexican empire; incredible hardware (including a fleet of 727 jets to transport his product); he even had plastic surgery to alter his appearance. And he was rich. At the time of his death from medical complications, his net worth was estimated to be around $25 billion, which would make him the richest criminal of all time on record. That may be quite an accomplishment, but it’s not exactly a career that is going to earn you much respect… except amongst other drug barons, of course.