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10 Facts About the World’s Most Despicable Conman

by Alan King
fact checked by Darci Heikkinen

There was once a man who fought through wars, survived the un-survivable, married into two of the most esteemed and wealthiest families of the 18th century, and was even regarded as a war hero. This man, however, grew to become one of the most cunning and convincing liars in human history. He caused the deaths of hundreds through a con that had never been done before and a scam that could never be done again.

This is the story of Gregor MacGregor, the most despicable conman in human history.

Related: 10 Con Artists Who Sold Things They Did Not Own

10 Married for Money to Buy Military Rank

When MacGregor turned 16, he enlisted into the British military, where he was posted to Guernsey to defend against a French invasion during the Napoleonic Wars. The French attack, however, didn’t go down well because, well…it never actually happened. As MacGregor waited for an enemy invasion that he was destined to never meet, he was met with something else entirely.

A young woman by the name of Maria Bowater had caught his eye. She was by all accounts a one-in-a-million catch to a simple soldier posted there for the war. Maria was young and beautiful, but most importantly for MacGregor, she was born into an exceedingly wealthy family with an admiral for a father.

To young soldiers, she was an impossible dream only to be admired but never claimed. However, for MacGregor, it truly was as they say: “You can resist beauty, but you cannot resist charm,” and MacGregor had plenty of that. So despite his class and the obstructive disapproval of Maria’s parents, MacGregor and Maria were married.

Once the ring was on Maria’s finger, MacGregor immediately seized his opportunity to begin spending his wife’s money to buy the rank of captain. Once captain, he transferred himself to Gibraltar, where he enjoyed Spain’s beautiful weather away from enemy threats for the next four years.[1]

9 Lied About Being Knighted

In 1810, MacGregor moved back to Scotland, wanting to show that he was no longer the same boy who had left all those years ago. He fought for both the British and Portuguese militaries and somehow married into an extremely wealthy family. Now, he wanted to prove that he was indeed a respected and commendable man.

So upon his return, he began boasting to his fellow countrymen that he had now been dubbed “Sir MacGregor,” claiming that through his adventures and advancements in status, he had received a royal decree to become knighted. This was a simple and believable lie that MacGregor knew he could get away with to gain even more merit—and possibly even some form of social advantage. Regardless, it still wasn’t deserved. It was a petty fabrication purely designed to satiate MacGregor’s dangerously growing ego.

In 1811, his wife Maria passed away, and her family cut MacGregor off. Seeking another advantageous marriage, he headed to Venezuela, which was in the midst of a war for independence. His fake knighthood proved beneficial to him in his new country, drawing the attention of Francisco de Miranda. Miranda appointed MacGregor to the rank of a cavalry officer, where he circulated among the elite.

Not long after, he married Doña Josefa Antonia Andrea Aristeguieta y Lovera, a member of Venezualan high society—and a cousin to to famed revolutionary, Simón Bolívar. He spent the next several years rising through the ranks until he had become a Brigadier-General.[2]

8 Found Some Success as a Military Leader

In 1816, MacGregor was placed at the forefront of over 600 troops. As their leader, it was his job to ensure that they successfully aided in reclaiming Venezuela from Royalist control. However, when MacGregor and his men landed in Ocumare, their entire campaign crumbled instantly. Their leader was forced to flee, taking the ships with him. MacGregor and his men were now left surrounded by the enemy, no thanks to their “wise and brave leader.” They were left with no boats or ships to sail along the coast in order to avoid conflict with the Royalists.

They had scarce ammunition and barely any provisions, and this still wasn’t even the worst of it. To make matters even more terrifying, the only way for them to make it back to safe ground was to trek across 300 kilometers (186 miles) of harsh swamp completely engulfed by Royalist control. This march was regarded as suicide, but MacGregor and his 600 troops had no choice, so the men bravely began their long journey across the devouring waters of the swamp while constantly being confronted by the enemy.

MacGregor had truly been thrown in with the sharks and was forced to practically run through a gauntlet that would mold him into a true leader. He used ingenious tactics designed to outmaneuver the enemy by tricking them into swamps and bogs. He even faced Royalist troops head on by having his men boldly collide with blockades on foot before puncturing through on horseback and pressing on through the saturated lands.

They traveled for weeks and were starving, battered, and fatigued. But in an astounding act of leadership, their inevitable deaths were avoided, and their long journey finally came to an end. They had made it to safety. Once MacGregor and his men were re-established in a secure Republican town, stories of MacGregor’s exploits had practically infected all the Republican camps and strongholds in a single night.

MacGregor was now regarded as a hero throughout Venezuela, a celebrated man who was now praised and, above all, trusted by the troops. Many flocked to serve under him, believing that he would ensure their safety with his brilliant leadership. Unfortunately, MacGregor went on to use this respect to feed his own agenda that would ultimately lead to the exact opposite of what he had spent weeks trying to avoid.[3]

7 Ever on the Lookout for His Next Adventure

MacGregor, during this period, was known by many as the Scottish man who married into the Bolivar family as well as a knight and war hero of Ocumare. His reputation had grown, and MacGregor used this to his advantage, knowing that men wouldn’t think twice about joining him. However, when it became apparent that the Spanish were largely defeated, he knew it was time to move on. MacGregor was then recruited to start conquering some viable ports in Spanish Florida—because, in those days, I guess that’s just what the boys did on the weekend. He began hiring dozens upon dozens of mercenaries in the United States, eventually gaining an army of around two hundred men. (Unfortunately, the U.S. frowned on its citizens fighting in foreign wars, so they soon had an issue with MacGregor.)

These men, however, were not young boys looking to make a name or take part in some grand adventure. No, these were hardened mercenaries, paid killers, and vagabonds. They knew of MacGregor’s exploits and knew that he would be a viable leader, but war hero or not, they wouldn’t fight for anyone unless they were getting paid. MacGregor, of course, knew this; and he definitely knew he didn’t have the money to provide payment for two hundred men.

Even if he did, what follows shows that there was no way he was going to part with a single coin. So MacGregor did what he did best—he concocted a plan. He promised all his men that he would grant titles to massive estates in Florida, estates MacGregor clearly didn’t own and would, in fact, never own. He also raised money by “selling” people land in the soon-to-be-conquered Florida.

This may seem surprising, but the reason he never actually claimed any land in Florida wasn’t due to his enemies overpowering him or because they outsmarted the esteemed hero of Ocumare. It was, in truth, due to his selfish neglect to simply not care. It might have become apparent to his men that MacGregor was far from the great man he was made out to be; right after he had conquered a town, he would begin drinking and lounging around, essentially doing nothing. MacGregor didn’t even set defenses for an inevitable counter-attack.

His men thought they were taking over a continent and possibly making history, or at the very least, getting a reward that would set them up for life. But in reality, MacGregor was just pillaging cities and sailing away with all their gold. One day, when these hopeful mercenaries awoke, all they saw was the back of MacGregor’s ship as it sailed away.[4]

6 Left His Men to Face Certain Death…Twice

In 1818, MacGregor attempted once again to take control of another country—Panama. This time, he brought with him around 500 men. He landed at the port of Porto Bello with 200 of his men and took control of the city. Then MacGregor became king and created one of the most viable cities to live in…

(I’m kidding, not a chance!) He went straight back to drinking and relaxing. Again, of course, he didn’t even attempt to set up city defenses.

A Spanish counter-attack to reclaim the city had begun, and MacGregor (probably still drunk during the siege) had no way of defending the town he had just claimed. So naturally, he fled by jumping out of a window, leaving his troops behind. A year later, MacGregor and his men went on one final siege. Though he was able to hire more than enough men, many deserted when they were not paid. However, apparently, some of these men still had enormous respect for the man even after he had failed two attempts at conquering territory.

This time it was at a royalist hold in Venezuela. Determined to make up for his mistakes, MacGregor reclaimed the stronghold and then proceeded to get drunk and again do nothing. The Spanish, of course, returned fire with an all-out attack. MacGregor was forced to escape, leaving all of his remaining men to be captured by the Spanish. These men were subsequently lined up and shot dead along the coast.[5]

5 A Drunken Land Grab

MacGregor was a wanted man now—the British, Americans, and the Spanish all wanted him dead due to his failed siege attempts and the fact he had abandoned so many of his so-called comrades to their deaths. So now desperate, alone, and in hiding, he began traveling along the coast of Nicaragua, a desolate and unforgiving world riddled with diseased mosquitos. An area aptly named the “Mosquito Coast.”

This harsh land was controlled by many local tribes descended from Native Americans and enslaved Africans. One, in particular, was led by a man named “King” George Fredrick Augustus. MacGregor and Augustus naturally clicked, spending their time on a drunken bender that lasted for days; it was during their drunken escapades that Augustus traded eight million acres of tribal land in exchange for rum and jewelry.

Augustus had no use for the land—I expect he doubted that MacGregor would find a viable use for it. However, MacGregor did manage to find a use for his new state-sized land that no one else likely would have dared to attempt.[6]

4 Fabricated the Existence of an Entire Country

The Fraudster that Sold an Imaginary Kingdom | Gregor MacGregor

MacGregor now owned more land than the entire island of Hawaii; unfortunately, the land was by all accounts useless. Well…by all accounts except for one. MacGregor was a visionary and knew there was a way he could turn this wasteland into a steady source of income, so he began his task of the construction of his new country: POYAIS! Or rather the construction of the lie that was Poyais.

There was no end to the amount of imagination and cunning MacGregor used in order to fabricate such an extreme con. First, he labeled himself as His Serene Highness, Prince Gregor MacGregor. Then, he and his wife returned to London. Surprisingly, he was still remembered as a war hero. So people believed his title because no one questioned it, and if they did, he had already created the “proof” he would need to quiet their inquiries.

MacGregor built offices in London designed to reinforce and legitimize his con. He used these to spread misinformation claiming that Poyais was already a well-established country with its own governmental system. He said their river beds were littered with gold and that the soil was so fertile it could produce three harvests a year. By fabricating a settler’s guidebook and spreading the word through local newspapers, MacGregor successfully conned over 500 investors.[7]

3 Caused More Deaths

Confidence Trickster Sir Gregor MacGregor | David Wilson’s Crime Files | BBC Scotland

MacGregor was overly successful in constructing his Poyais con, managing to convince hundreds of settlers to buy land in his newfound country. Unfortunately, these people were not welcomed to the beautiful utopia MacGregor had promised them. Instead, they were greeted by the harsh jungle and desolate swamps.

Incredibly, MacGregor was so convincing with his con that they simply believed they had made a wrong turn and docked further away from the city. They sailed up and down the coast, desperately looking for a world that didn’t exist. Eventually, they started to run out of supplies due to a hurricane forcing them to settle along the Mosquito Coast.

The mosquitos, who had inhabited the shores long before the deceived settlers, brought nothing but death with them in the form of malaria and yellow fever. More than 200 of these settlers—made up of the elderly, families and children looking for a place to settle—were sent to their graves because of MacGregor. However, a few fortunate souls were saved by a passing ship, but even their stories of the horrors and deceit they faced didn’t change anything: the Poyais con still continued.[8]

2 The Poyais Con Lasted Another 15 Years

The survivors of the Poyais scheme began to spread the word of MacGregor’s scam. Naval ships were even starting to intercept potential settlers inbound for “Poyais.” The story was rapidly spreading, and people became increasingly aware of MacGregor’s lies, some of the most egregious in history.

However, it still didn’t stop. MacGregor’s scheme was so well formulated that it managed to last for over 15 years. People were still falling for it in England, but now it was also in France. MacGregor’s con lasted from 1822 until 1837. And who knows how many people he convinced to set sail to a paradise that was really a diseased hell…never to return?[9]

1 An Unfair Punishment

Even after the stories had traveled across the globe, it didn’t change anything. MacGregor had already used the money he had stolen to move to France, where he started the same scheme all over again.

The French government caught on to MacGregor’s con much quicker, however, and he was arrested. The story goes that MacGregor simply put the blame on his French collaborators. He was quickly acquitted for his crimes, only serving roughly six6 months in a French prison.

He then moved back to Venezuela after his wife died. Surprisingly, he was given a general’s pension by the new Venezuelan government, and he lived there peacefully until he passed away in 1845 at the age of 58.[10]

fact checked by Darci Heikkinen