10. Bernard Madoff
- $820 million
The former NASDAQ chairman admitted to operating the largest Ponzi scheme in U.S. history after his sons turned him in to the authorities in 2008. In 2009, “Bernie” Madoff plead guilty to 11 federal felonies. The Madoff investment scandal dated back to the mid-80s and racked up nearly $65 billion from client accounts.
Madoff received a 150-year prison sentence in 2009. He was the “first prominent practitioner” of “legal kickbacks,” a highly-debated financial practice. The fund set up to reimburse customers affected by the Ponzi scheme is reportedly on its ninth distribution, and the total handed out so far is $11.4 billion.
9. Joaquin Guzman Loera – ‘El Chapo’
- $1 billion
El Chapo (which means “shorty”) was nicknamed for his 5’6 height. Regardless of his stature, the Mexican drug lord was called the most powerful drug trafficker in the world by the U.S. Department of the Treasury.
El Chapo headed the Sinaloa cartel responsible for bringing nearly a quarter of the illegal drugs that entered the U.S. from Mexico. The infamous drug kingpin notoriously escaped prison twice and is currently preparing for a Brooklyn trial in April 2018. He pleads ‘not guilty to a 17-count indictment on heading a criminal enterprise and conspiring to murder.
8. Al Capone
- About $1.3 billion
Whether you know him as “Public Enemy No. 1” or “Scarface,” the infamous gangster amassed a multi-million dollar fortune through bootlegging, prostitution and gambling during the Prohibition Era. Capone is allegedly responsible for the Saint Valentine’s Day Massacre in 1929 and attempted murder on Bugs Moran, head of the North Side Gang.
While he wasn’t indicted for his racketeering, Capone served six-and-a-half years for income tax evasion. He was released and later died in Miami in 1947.
7. Allen Stanford
- About $2 billion
In 2012, the American billionaire was found guilty of a $7-billion Ponzi scheme, money laundering, and obstruction of justice, The Telegraph reports. Federal agents raided Stanford Financial offices in 2009. The Security Exchange Commission charged Allen Stanford with “massive ongoing fraud” in 2009, and he was sentenced to 110 years in prison. He is currently serving his time at the United States Penitentiary, Coleman, in Florida.
“I didn’t do anything wrong,” Stanford told the BBC in 2016, “Will I apologize? No. Mark my words… I am going to walk out the doors of this place a free man.”
6. Leona Helmsley
- $2 billion
“The Queen of Mean” called taxes something “Only the little people pays,” and then received 16 years in prison for tax offences. Her prison sentence fittingly began on April 15th (Tax Day). Leona and her husband accumulated famous New York City real estate, including the Empire State Building and Flatiron Building, in their heyday.
Rudy Giuliani, a U.S. Attorney back in 1988, indicted Leona, her husband, and two of their associates on tax charges, including extortion. The Helmsley’s were accused of using money from their real estate empire to stock their Connecticut summer home with luxuries like a $1 million marble dance floor and a $45,000 silver clock.
5. Carlos Enrique Lehder Rivas
- $2.7 billion
The Medellin Cartel co-founder and drug lord began a life of crime dealing stolen cars, marijuana, and eventually cocaine. A “titan of the cocaine industry,” Lehder oversaw “legions of gunmen, racing boats, airplanes, a ranch with a racetrack and even his own small neo-fascist party.”
There are multiple theories about Lehder’s capture, including that his own cartel wanted him out of the picture and that Pablo Escobar himself provided the police with Lehder’s location. Lehder was tried and sentenced to life without parole plus 135 years, which he got reduced to 55 years total in 1992. Lehder remains imprisoned in the U.S.
4. Khun Sa
- $5 billion
Khun Sa, known as a “publicity-loving Golden Triangle drug lord,” headed opium trafficking from 1974 to 1994. During this time period, he controlled an estimated 70% of the Golden Triangle’s heroin business. He used the money to build an army and large-scale heroin laboratories.
Khun Sa’s empire traded opium for guns to gain control over large parts of the Shan region. Khun Sa was a guerrilla leader and self-dubbed “King of the Golden Triangle.” He surrendered to the Burmese authorities in 1996 under the condition that he received government protection. He died of unknown causes in 2007 at age 73.
3. Viktor Bout
- $6 billion
Bout was convicted of conspiracy to kill U.S. officials and aiding the terrorist organization FARC. He was also charged with the wire fraud and money laundering that experts anticipate helped him amass his billion-dollar fortune.
Bout was sentenced to 25 years minimum in 2012. The 2nd U.S. Circuit Court of Appeals in New York rejected his contention. In 2014, Bout hired former U.S. Attorney General John Ashcroft to represent him in a new trial to overturn his conviction. As recently as 2016, Bout “dared” then-President-elect Donald Trump to pardon him if he took office.
2. Amado Carillo Fuentes
- $25 billion
Allegedly the second-richest drug lord, Amado Carillo Fuentes, worked with infamous drug kingpin Pablo Escobar to smuggle cocaine and other drugs from Columbia into Mexico U.S. Fuentes built a multibillion-dollar drug empire and made an estimated $25 billion-plus in revenue from his illicit activities.
Fuentes evaded the DEA his entire life. In 1997 he died from an alleged eight hours of extreme plastic surgery to alter his appearance. The plastic surgeons who operated on Fuentes were found dead afterward — encased in concrete inside steel drums — and reportedly showed signs of torture.
1. Pablo Emilio Escobar
- $9 to $30 billion
The “King of Cocaine” became one of the world’s richest people by the time he turned 35. It’s impossible to verify how much Escobar made in total, but it’s estimated to be nearly $30 billion. He brought in an estimated $420 million a week, smuggling in an estimated 80% of the U.S. cocaine supply in the 1980s.
Forbes estimated Escobar’s personal net worth at $3 billion in 1989 as one of the “World’s Top Billionaires,” recognizing that not all of them made their money legally. Escobar bought various residences and safe houses with his wealth. He escaped La Catedral, his personal “luxury prison,” and spent the rest of his life evading the authorities. He died in a shootout 16 months after his escape.