Pablo Escobar
As a teenager, Pablo Escobar would steal tombstones and sell them to smugglers in Panama. From those devious roots, he entered the coca business in the 1970s, just as the U.S.'s obsession with the highly addictive drug began. Thanks to his ruthless ambition, Escobar built up Colombia's now infamous Medellin cartel into a powerful drug-trafficking enterprise that by the 1980s controlled more than 80% of cocaine shipped to the U.S., making him one of the 10 richest people in the world. After his death (he was gunned down at age 44 while on the run), books and movies shed light on just how lucrative his empire was. His son Juan Pablo Escobar (who changed his name to Sebastian Marroquin) said his father once burned some $2 million to keep himself and his daughter warm while they were on the lam. Another tale said Escobar once offered to pay off his country's $10 billion national debt. But his reign was not just lucrative: Escobar was also one of history's most violent criminals. The deaths of three Colombian presidential candidates, an attorney general, a Justice Minister, more than 200 judges, dozens of journalists, more than 1,000 police and countless ordinary citizens are all attributed to his rule.