Pancho Villa Mexican Revolutionary and Train Robber 1878-1923

Considered a violent, marauding outlaw to some, and a heroic revolutionary to others, Pancho Villa was anything but your average citizen. Born in Mexico to peasant parents, Villa escaped into banditry after shooting a man accused of raping his sister. He spent his twenties running with a bandit gang and stealing mules. He was sentenced to death for thievery and assault, but escaped the charge thanks to connections he’d made selling his stolen goods to high ranking police officials.

An ambitious and charismatic leader, Villa joined the Mexican Revolution in 1910 after a decade of evading the law. The revolution benefited from his continued banditry as he paid for his troops and supplies by stealing land from the wealthy, robbing banks, stealing and commandeering trains, printing his own money and even allowing a Hollywood film crew to film his battles in return for a 50% share of the profits.

During his 10 year reign as a commander in the Mexican Revolution, he was often greatly outmatched, yet won several key battles and outran a 3000 man strong year long manhunt led by General John J. Pershing and the US Army. He also inspired dozens of future movies while himself starring in four, and reportedly escaped a second death sentence while facing a firing squad, this time thanks to a last minute telegram from then Mexican president, Francisco Madero. Perhaps most impressive, he never drank alcohol during this entire period.

When he finally retired and signed a peace treaty with interim president Adolfo de la Huerta in 1920, he had accumulated enough money to purchase a large Hacienda with extensive land and livestock which he generously transformed into a community for his loyal soldiers. He was finally assassinated in 1923 after returning to political matters, many believe upon orders from then President Alvaro Obregon.

Pablo Escobar Columbian Drug Lord 1949-1993

were a politician, policeman, judge, reporter, rival drug runner, DEA agent, or alive in general in Columbia during the 1980’s, there’s a good chance Pablo Escobar tried to kill you. If you were a poor young student with an interest in soccer, he likely paid for your uniforms and donated your team a field.

At the height of his power Forbes magazine listed him as the 7th richest man in the world; worth an estimated $24 billion. He was considered more wealthy and powerful than Columbia’s entire federal government, supplying the United States roughly 80% of its annual cocaine all while holding massive orgies, getting stoned, and regularly sleeping past noon. He bought private airstrips, owned dozens of homes throughout his home city of Medellin, and used bribes, threats, murders, kidnappings and regular bombings throughout the nation’s cities to control politicians, judges, the police force, and at times the President of Columbia. He even spent time as a member of the Columbian congress, essentially buying a seat and even offering to pay off the $10 billion national debt.

Widely known as the most dangerous man in Columbia, if not the world, half the country refused to punished him for fear of retribution, while the other half viewed him as a national hero who sponsored sports teams, built stadiums and churches, fueled the nation’s economy, and regularly gave back to the nation’s overlooked poor.

When his exploits finally landed him in jail, it was in a sprawling private jail he had built for himself with a soccer field, gym, Jacuzzis and a steady stream of female escorts. After several years and failed attempts, and through the secretive collaboration of American agents and local authorities as well as a vigilante group made up of relatives of his victims, Escobar was finally gunned down as he fled across rooftops wearing a pair of jeans and no shirt.

Sir Henry Morgan Welsh Pirate 1635-1688

Pirates were the original Bandidos, and in the early colonial days of Latin America, no pirate was more feared and admired then Sir Henry Morgan. A charismatic, heavy drinking leader of roughneck sailing outlaws, Morgan commanded some of the most ingenious, outrageously successful sacks on the Spanish cities of Central and South America in all of history.

Ruthless, clever, and incredibly bold, Morgan never limited himself to attacking other ships, but chose instead to attack and burn to the ground some of the wealthiest cities of Latin America—often returning a for second raid a few years later—stealing ships, gold, and weapons before ransoming its wealthiest citizens for additional loot and information.

In one of his most famous raids, in the Venezuelan lakeside stronghold of Maracaibo, the Spanish citizens not only knew of his attack ahead of time, but held the advantage of superior ships and large, elevated fortresses stocked with cannons. Morgan succeeded anyways by using sneak attacks with dugout canoes, faking land assaults, and stocking one of his own ships with slowly burning explosives and life-size cutout statues of pirates to bait the Spanish in close for an attack before blowing up both vessels and allowing the pirates to slip away.

His victorious raids were so clever, brutal, and successful that over time the colonial Spaniards mixed their fear and hatred of him with admiration, and entire armies often abandoned their posts at the mere sight of him, choosing to flee as cowards rather than die at the hands of this fearsome and undefeatable ghost.

By the end of his career, Morgan’s men had stolen tens of millions of dollars in gold, silver and other treasures while inflicting the modern equivalent of billions of dollars in damages to the cities they attacked. Morgan retired to the wicked, pirate stronghold of Port Royal, Jamaica where he was rewarded with the post of Acting Governor. Though many of Port Royal’s pirate citizens were killed by a horrendous earthquake in 1692, Morgan—as he’d done his entire life—escaped the revenge just in time, dying four years earlier to alcohol induced dropsy.