10 Bernard “Bernie” Madoff
Bernie Madoff was a career financier. After high school, Madoff earned a degree in political science, tried law school, and dropped out to found his own Wall Street firm, Bernard L. Madoff Investment Securities. All it took to start his firm was a little hard work, grit, and… a large loan and many connections from his father-in-law. Shocker. The company took off, becoming one of the biggest market maker businesses on Wall Street, and helping to create the NASDAQ stock market, which helped launch Madoff to the role of NASDAQ chairman. This afforded Madoff a lot of prominence and power, and because of that, trust. Hopeful investors flocked to give Madoff their money, under the seemingly unbeatable promise of constant 10-12% returns monthly. The only problem was, he built his entire operation on a lie. Not just any lie, it was the biggest Ponzi scheme in history. Madoff took money from thousands of would-be investors over the course of three decades. He eventually accrued around $36 billion, and instead of investing it as promised, deposited much of it into his personal Chase account. He was able to keep up the appearance of regular investing and returns by using a portion of the money gained from new investors to pay out old investors, in an ever-growing Ponzi scheme that eventually grew too large to avoid attention. Madoff’s whole scheme was caught, but not before he ballooned his own net worth to $826 million. We wonder if all that money is worth his 150-year prison sentence.
9 Joaquín “El Chapo” Guzman
Joaquín Archivaldo Guzmán, better known by nom-de-crime El Chapo, was born into a poor family in Mexico and from an early age was vocal about wanting a better life. Through his uncle, Pedro Avilés Pérez, he found that life in the form of organized crime. His first job of this new life was transporting drugs by plane for the drug lord Héctor “El Güero” Palma, a part of the dominant Guadalajara Cartel. Once again, Guzman repeatedly made it known he wanted more, asking, and often demanding, to increase his share of the operation. Between his ambition and his reputation for violently dealing with opposition—but maybe more the violence—he consistently rose through the ranks. Guzman worked with a veritable who’s who of the Cartel. When the Guadalajara Cartel split in the late 80’s, Guzman formed his own Sinaloa Cartel, which controlled a vast swathe of Mexico and trafficked drugs between Colombia, Mexico, and the U.S. By 2003, the Sinaloa Cartel, with Guzman at its lead, had risen to become the wealthiest and most powerful of the cartels, making Guzman the top drug kingpin in all of Mexico. This paid off handsomely, earning him about $1 billion at his peak, which allowed him to construct entirely separate empires in the worlds of shipping and transport. Guzman is currently serving a life sentence. But for a few decades, he certainly obtained his dreams of a better life. Fiscally, anyways.
8 Al Capone
Perhaps America’s most famous mobster, and the real-life “Scarface,” Al Capone helped create and run a criminal empire for years- all before he was 33. He was born to poor immigrants and chose to break the cycle of poverty by joining a series of gangs, wherein he engaged in all manner of criminal enterprise- gambling, bootlegging, racketeering, extortion, and bribery. He caught the attention of a Chicago crime boss named James “Big Jim” Colosimo and began his ascension to the top of the Chicago crime world. By age 26, he was the boss of the largest organized crime group in Chicago, a sect of the Italian Mob known as the Chicago Outfit. Capone ordered or committed at least 33 known hits as a boss, the most infamous of which is the Saint Valentine’s Day Massacre. He also used his leverage to influence local elections, changing the Chicago area’s political climate to suit his needs. All told, his criminal enterprises earned him the equivalent of $1.3 billion in today’s money. Oddly enough, the crime that finally brought Scarface down? Tax evasion.
7 Griselda Blanco
If the number of nicknames is a measure of your legacy, and it certainly is, then Griselda Blanco has earned a unique spot on this list. Blanco, aka La Madrina, the Black Widow, the Cocaine Godmother, and the Queen of Narcos, was a Colombian drug lord. Working in the Medellín Cartel, she helped to pioneer the Miami drug trade, transporting huge amounts of cocaine into the city between the 1980s and early 2000s. She was perhaps most notable for her violence. She and her fellow cartel members, dubbed by the media as the Cocaine Cowboys, have been estimated to have committed up to 2,000 murders while transporting cocaine from Colombia into the U.S. Blanco was one of the richest and most dangerous women in the world at the height of her power, raking in as much as $80 million per month. She became the first-ever billionaire female criminal, with an estimated net worth of $2 billion.
6 Allen Stanford
Allen Stanford is one of those men who looks, on the surface, to be an upstanding, influential leader of society. Stanford was the chairman of the Stanford Financial Group, a group of companies specializing in banking and wealth management. He and his company funded cricket, golf, polo, and sailing events for charity. He even funded a movie that featured Abigail Breslin, a film about the joy of philanthropy. Of course, all of this hid a darker center to Stanford. In addition to his surface-level dealings, Stanford was engaged in what the SEC would later call “massive ongoing fraud” and a “massive Ponzi scheme.” The Ponzi scheme eventually grew to encompass $7 billion in assets and included money laundering, bribery, and political manipulation. Though convicted by a jury and sentenced to an impressive 110 years in prison, Stanford nonetheless managed to wrack up an equally impressive $2 billion before it was over.
5 Khun Sa
Khun Sa has some impressive, and awful, credentials. Before his death, he would come to be called the Opium King, the King of the Golden Triangle, and best/worst of all, the American ambassador to Thailand once dubbed him,” the worst enemy the world has.” Khun Sa was Shan by ethnicity and spent much of his life fighting for Shan independence throughout Southeast Asia. His success in that venture is questionable, if only because his success in drug trafficking and the formation of his own paramilitary group ran at times counter to that goal. From the mid-70s to the mid-90s, Khun Sa ran a massive opium smuggling operation in the Golden Triangle, where he was considered the dominant opium warlord. During this time, he controlled an estimated 70% of the Golden Triangle’s heroin business. His power and wealth allowed him to retire comfortably, with around $5 billion to his name.
4 Viktor Bout
There is a lot of money in selling weapons. Especially if you’ll sell them to practically anyone. Over two decades, Viktor Bout proved this true. Bout was trained in the Soviet Armed Forces, including possibly the KGB, where he mastered at least six languages. He retired from armed service to start an air freight business. That he did, a company called Air Cess, though his planes would soon come to carry more than food and supplies. For two decades, Bout and Air Cess smuggled weapons to whoever would buy them, including several West African countries which were subject to arms embargoes by the U.N. It was one sale, however, that brought Bout down. He attempted to sell an entire army’s worth of arms to the radical anti-U.S. Colombian guerrilla group FARC. Bout was caught and convicted of conspiracy to kill U.S. officials, aiding the terrorist organization FARC, wire fraud, and money laundering. Before his capture, he did manage to amass $6 billion, so at least in prison, he’ll be able to afford the nice cigarettes.
3 Leona Helmsley
Leona Helmsley was a famous condominium broker and hotelier whose ruthless business practices and disposition earned her the nickname the Queen of Mean. She was known in equal parts for her abuse of her staff and her tendency to dispute payments to and from contractors, vendors, and tenants. During court proceedings in 1985 over a lawsuit about disputed payment, the contractors revealed that they were billing most of their work illegally to Helmsleys’ hotels as business expenses. Then the dominos began to fall. After a criminal investigation, Helmsley was convicted of conspiracy to defraud the United States, tax evasion, filing false personal tax returns, and assisting in filing false corporate and partnership tax returns. On top of that, they got her for mail fraud, too. She served a couple of years’ time, but in exchange made a decently comfortable $8 billion.
2 Amado Carillo Fuentes
Amado Carrillo Fuentes was a Mexican drug lord who headed the Juárez Cartel. Fuentes gained the nickname The Lord of the Skies because of the vast fleet of jets he used to smuggle drugs. As far as smugglers and cartel members go, Fuentes was pretty unremarkable. He joined the cartel because of the influence of his uncle, cartel leader Don Neto. Once inside, his trajectory was fairly normal, and he never attained the fame of either of his peers El Chapo or Pablo Escobar. He did, however, help grow and control a multibillion-dollar international drug empire, and in the process make himself a cool $25 billion. Ironically, what killed this relatively fame-less drug lord was complications from plastic surgery to give him a new face.
1 Pablo Emilio Escobar
There is no one like Pablo Escobar. The “King of Cocaine” became the richest criminal in history and one of the world’s richest people. He creating a near-monopoly on the cocaine trade in the U.S. for years. His empire is unparalleled in history, and frankly sounds made up when read aloud. His organization moved 70 to 80 tons of cocaine into the U.S., or 80% of the country’s total, every month, and hundreds of more tons into countries on every continent but Antarctica, which altogether earned him $420 million per week. Though his exact net worth is unknown, it is thought to have reached the equivalent of $59 billion in modern dollars. Even though it comes at an incalculable criminal cost, it is very hard not to respect $59 billion, Pablo. Very hard.
