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Meet The Wealthiest Criminal Kingpins In History- Money Rolls In Even When Locked Up!

If you want to be a millionaire, it’s not really advised that you turn to a life of crime, that much should be obvious. However, some have completely ignored the law and became filthy rich by doing so. While most of us take out our inner criminal in video games, some have had the cojones to launch international operations and hire police onto their payroll (while the rest of us are getting pulled over for rolling through stop signs!).


Of all of the criminal kingpins that ever lived, here are the ones that made the most money. Remember not to try this at home, you’ll notice the common place these people ended up; dead, or in prison!

#20 – Frank Lucas ($52 Million)

According to Frank Lucas’s biography, he is a retired drug dealer. It’s a good thing he’s retired, too, because that would be a strange thing to put on a resume. Despite making millions in the drug trafficking game, he only spent 12 years in prison in his life, including 5 years of a 70 year sentence. You, on the other hand, would probably get 3 months for a speeding ticket.

He specialized in getting Heroin into the United States and he did it in one of the worst ways possible, by smuggling it inside of dead American soldiers’ coffins. They even made a movie based off of Lucas in 2007 starring Denzel Washington, American Gangster.

#19 – José Figueroa Agosto ($100 Million)

José Figueroa Agosto is a guy who really does not like dealing with authority, and he’s pretty much the personification of a Grand Theft Auto character.. After becoming the biggest drug dealer in all of Puerto Rico, he was arrested and sentenced to 209 years in prison. He promptly escaped though and got out of the country to the nearby Dominican Republic.

Instead of turning his life around and laying low in the Dominican, Figueroa Agosto went back into the drug trafficking game. He was arrested and released using another identity, then was chased again by police in 2009. It wasn’t until 2010 that he was caught again, and he even tried to escape that! Figueroa Agosto has $100 million in cash stashed in a spot he refuses to disclose to police, so if you can find it, it’s yours! But you have to split it with the feds.

#18 – George Jung ($100 Million)

George Jung is from Boston, Massachusetts and earned the not so creative nickname of Boston George. In the 1980s, Jung was the person that brought almost all of America’s cocaine to the shores. He was arrested in 1984, however, and had to spend 20 years in jail, finally being released in June of 2014.

To help soften the blow of a two decade long stint in jail, they made a movie about his life. Most people would be thrilled to see that Johnny Depp was picked to play them in a biopic, but since Jung was locked up he couldn’t enjoy the fame. He is now helping to write a sequel to 2001’s Blow. As long as the chubby guy from Boy Meets World is in there again, we’re all excited to see it.

#17 – Nicky Barnes ($105 Million)

Nicky Barnes had a much better nickname than Jung, as Mr. Untouchable. He’s still alive at 81 years old and started out as a heroin user. After the young Barnes went to jail for heroin use, he cleaned up, and got into the selling business instead! There’s a lot more money in selling drugs than buying drugs, apparently.

Barnes made a lot of his money by avoiding police for a long time, since many of them were on his payroll. By claiming he was untouchable, he made Jimmy Carter so mad that the President himself forced the DEA to arrest Barnes and he received a life sentence. He got out in 1998 though, quit the drug selling business, and made money off of telling his story instead. You know you’ve made it when the President personally sees to your arrest!

#16 – Paul Lir Alexander ($170 Million)

Alexander, or El Parito Loco as he was known, was quite the businessman. While he was smuggling cocaine into the US, he was shutting down other smugglers with the help of the Federal Government by basically pretending he was the good guy. He amassed a fortune by being the only game in town and soon moved to the US from Brazil.

Alexander was finally caught while living in America, and had to spend 12 years in prison. He was shipped back to his home country of Brazil in 2005 and was sentenced to another 42 years. Alexander was able to leave the prison in 2011 on work release, but escaped from his job. The police still haven’t found him, even though he’s on Facebook. Status update: LOL can’t find me!

#15 – Zhenli Ye Gon ($300 Million)

Zhenli Ye Gon’s story is an interesting one. Instead of working the streets and selling drugs, he is an executive for a pharmaceutical company in Mexico, where he would bring in pseudoephedrine from China. He made Mexico his home after he started netting a lot of money, and is a member of the Sinaloa Cartel.

His charges are still pending, so he hasn’t had to do as much jail time as a lot of the people on this list. However, he had some of his assets seized, which included more than $200 million in US Dollars alone. He also had money from Mexico, Europe and Hong Kong stashed in his hideout. Most of us can only hope to be rich in one country, let alone four!

#14 – Joseph P. Kennedy, Sr. ($400 Million)

Joseph Kennedy is the father of President John F. Kennedy, and served as the Ambassador to the United Kingdom during his career. This isn’t how he made the bulk of his fortune, however. He was born into a wealthy family, but made a killing by smuggling booze during the prohibition era.

It has not been confirmed that he was actually doing it, but it was kept on the down low to help preserve the Kennedy name. He took the money that he made from bootlegging and did the wise choice of investing it into real estate. Put it all together and you have one rich politician. So the next time there is a prohibition on booze in this country, you too can make millions by smuggling!

#13 – “Freeway” Ricky Ross ($600 Million)

Don’t confuse Freeway Ricky Ross with rapper Rick Ross, even though they look similar. Freeway Ricky Ross earned millions by smuggling and dealing crack cocaine in Los Angeles during the 1980’s, when it was at its peak use. He was arrested in 1996, after a sting operation by the feds had him purchase more than 200 pounds of the white stuff.

Freeway Ricky Ross’ sentence was reduced, and he was released in 2009. He was such an important drug dealer that he was called in as part of the Iran-Contra hearings. He cashed in on his life’s story by releasing a book in June of 2014. Freeway Ricky Ross also sued the previously mentioned rapper for using his name (since the rapper’s real name is William Roberts).

#12 – Rafael Caro Quintero ($650 Million)

Rafael Caro Quintero created the Guadalajara Cartel in Mexico and made it a family business by starting it with his brother. It’s not quite like the startups you hear about today, but they made a lot of money. He was wanted for multiple murders as part of the cartel, including a federal agent and a pilot (who was not flying at the time of the murder, thankfully).

Quintero was sentenced to 40 years in jail for murder (but not for drug dealing) in 1985, however, he was released from a Costa Rican prison in 2013. The United States and Mexico would still like to have a word with him, so he is at large according to these federal agencies. Quintero is still one of the most wanted men in the world according to Interpol as well (not the band).

#11 – Joaquín Guzmán Loera ($1 Billion)

Since 2009, Forbes magazine has actually named Joaquín Guzmán Loera one of the most power people on Earth today and as Public Enemy Number One. He was the head of the famed Sinaloa Cartel in Mexico, and was top dog in the drug dealing business starting in 2003.

Loera was arrested in 1993, but used his vast wealth to entice the guards at the Guatemalan prison to let him walk in 2001. There’s no word as to why it took him 8 years to think of that brilliant idea. Mexico and the United States were not pleased by this and offered a substantial award for his arrest. After 13 years of searching, the Mexican government finally got their man in February of 2014. He went peacefully, too, which is a rarity among the people on this list.

#10 – Al Capone ($1.3 Billion)

Al Capone is perhaps the most notorious gangster in the history of the United States. When Capone was young, he moved from New York to Chicago to become a bodyguard to alcohol smugglers during the prohibition. Since evidence was hard to come by before technological advances, it was hard to arrest Capone. Nowadays, he would have been arrested within a week and had an episode of NCIS based off of him.

However, the US Government did get him, but only on the charge of tax evasion. He was well liked by the common man, but that didn’t do much for him in prison. He was sentenced to 11 years for the tax crimes but only served 8. He passed away just a few years later from cardiac arrest when he had a stroke, which was only a matter of time considering his gangster lifestyle.

#9 – Griselda Blanco ($2 Billion)

Griselda Blanco is one of the most interesting people on this list and the only female. She became one of the leaders of the Medellin Cartel from Columbia and set up shop in Miami. She brought a massive amount of cocaine into the United States every year, and her harsh ways earned her the nickname of The Black Widow.

Blanco’s relations with the cartel turned sour after she had a member of the Ochoa family murdered (more on them later) because she didn’t want to pay for a shipment. For non drug dealers, that’s basically like killing an eBay seller. She then went on the run for many years, but was found by drug dealers in 2012, where she was shot in a drive-by incident.

#8 – Carlos Lehder ($2.7 Billion)

Carlos Lehder is one of the founding members of the Medellin Cartel in Columbia. Like many of the people on this list, he helped get cocaine into South Florida (which really seemed like the place to be in the 1980’s) to spread it across the country. He was arrested at a very young age for car theft in Connecticut, where he met George Jung. The two would form a beautiful friendship.

After their release, Lehder and Jung sold enough cocaine to buy a stolen airplane (when they could have just stolen an airplane themselves) to cut out the middle man. This is where Lehder made all of his money, but ended up getting caught by federal agents. He is still serving time in prison for all of the illegal smuggling. Lehder was also featured in the film Blow, but he wasn’t played by an A-List star like Jung was (Johnny Depp).

#7 – The Rodríguez Orejuela Brothers ($3 Billion)

The Rodríguez Orejuela brothers consist of Gilberto and Miguel Rodriguez Orejuela. These two, along with another partner, created their own cartel known as the Cali Cartel to show that entrepreneurship even extends into the drug dealing world. They started by smuggling marijuana, but soon upgraded to cocaine. They were responsible for nearly all of the product in the United States and Europe.

The Rodríguez Orejuela brothers were arrested in June of 1995, when the Colombian police pulled the trigger on a search warrant. The raid turned up a lot of evidence and they were sentenced to prison. They were freed for six months between 2002 and 2003, but were promptly re-arrested when the court realized what they did. The court extradited them to the United States, where they are still imprisoned.

#6 – José Gonzalo Rodríguez Gacha ($5 Billion)

Not surprisingly, Gacha was also a member of the Medellin cartel. Due to the fact that he made so much money, Forbes was forced to list him as one of the world’s richest men in 1988 (though a lot of the people on that list probably partake in illegal activity themselves.) The cash kept flowing in until President George H.W. Bush ordered a crackdown on money laundering in the drug dealing business, and had Gacha specifically in mind.

This caused Gacha to hide some of his money where the feds couldn’t seize it. He racked up more charges after leading the murder of more than two dozen men. The authorities closed in on him quickly. Instead of going quietly, he and his men engaged in a gunfight where his son was killed. He then took his own life by handling a live grenade and pressing it up to his face. Despite all of his enemies, his funeral was attended by thousands.

#5 – Khun Sa ($5 Billion)

Khun Sa dabbled not only in drugs, but also in the very lucrative weapons smuggling department. He was trained in battle at a very young age, and built his own army during the Chinese Civil War. The army quickly grew and began to deal in gun and opium smuggling.



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