Gregor MacGregor, The Most Despicable Con Man In History

If we told you there was a man who fought through wars, survived the unsurvivable, and married into two of the most esteemed wealthy families of the 18th century, you might think it was a particularly unrealistic movie plot. But it isn't. It's the life story of a very real person, who also happens to be one of the most notorious conmen to ever run a racket. Today, we're telling you the story of Gregor McGregor, the most despicable conman in history. But before we sign away our life savings, be sure to subscribe to the Weird History channel. And let us know in the comments below what other historical hustlers you would like to hear about. But for now, no tricks, just history. Gregor McGregor was born on Christmas Eve in 1786, making Christmas Grift a perfectly reasonable nickname for the future confidence man. Boy, they really should have called him that. It was right there. When he was 16, he joined the British military and was immediately sent to defend Guernsey against a French invasion. Gregor never got to defend, though, because, well, the invasion never came. But Gregor walked away with something even more exciting than a battle victory, a lovely lady. While stationed in Guernsey, a young woman by the name of Maria Bowater caught Gregor's eye. She had everything a simple soldier could want. She was young, beautiful, and filthy, stinking rich. A young soldier could only dream to win the heart of a gorgeous woman born into a rich admiral's family. But McGregor possessed something most other chumps didn't, a whole lot of charm. Despite their vast class differences and the disapproval of Maria's parents, McGregor managed to woo Maria into marriage. As soon as the rings were exchanged, McGregor went to work spending his wife's money to purchase himself the rank of captain. And when you're captain, they let you transfer yourself to Gibraltar, where Gregor could live in the lap of luxury, safely away from enemy threats for the next four years. In 1810, McGregor moved back to Scotland to show off his new life, his impressive military career, and his rich and beautiful wife. Basically, he wanted to rub how well he was doing in everyone's faces, like a high school reunion. You know the friend who lived abroad, comes home, and starts speaking with a different accent and annoys the living snot out of everyone? That was McGregor. He started telling anyone who would listen about his adventures and promotions, even going as far to say that by royal decree, he had been knighted Sir McGregor. Since this was before the internet, McGregor knew nobody would check up on his claim. And he began to reap all the social benefits that come with stolen valor, mainly a big head and a giant ego. But when Maria died in 1811, Gregor found himself cut off from his family's wealth. So he did what any man does when his in-laws disown him. He went to Venezuela. The country was in the midst of a war for independence, and Gregor was able to use his fake knighthood to gain the rank of a cavalry officer, which he used to circulate among the elite. It turns out that war was a bit like McGregor's version of Tinder, because his made-up military credentials allowed him to marry yet another member of high society when he met the cousin to famed revolutionary Simon Bolivar. Sir Gregor would spend the next several years rising the ranks all the way up to brigadier general. In a total nightmare scenario for anyone who has fudged the resume, McGregor somehow found himself in charge of over 600 troops in 1816. It's like those nightmares where you forgot to study and you aren't wearing any pants and you command over 600 troops. Their job was to keep Venezuela from falling under royalist control. However, almost as soon as McGregor and his troops landed in Okumare, the entire campaign imploded. Simon Bolivar was forced to flee, leaving McGregor and his men all alone with no boats or ships to aid them in battle. With little ammunition and hardly any provisions, McGregor and his men were forced to trek through 300 kilometers of harsh swamp to get back to safety. To make matters worse, the swamp was crawling with royalist soldiers. Hate it when that happens. By sheer brute force, McGregor's men were able to break through the blockade first on foot, then on horseback. This trek lasted weeks, and the starving, battered, and fatigued men finally found their way out of no man's land with their inevitable deaths avoided. The stories of McGregor's triumph through the murder swamps began to spread like wildfire. Gregor was now regarded as a hero throughout Venezuela, praised and trusted by the troops. And he actually earned that praise legitimately. Nice work, Gregor. As you might expect, this first taste of genuine esteem went directly to McGregor's head. Many flocked to serve under his command, which McGregor would only use to feed his own ego and agenda. McGregor had gained a notable reputation as a heroic Scottish knight who married into the Bolivar family and things were pretty sweet for him. But he craved more adventure and notoriety. Around that time, McGregor was told that conquering some viable ports in Spanish-controlled Florida would be beneficial for expanding Republican operations further in Latin America. To accomplish this, he gathered up around 200 US mercenaries who had heard of Sir McGregor's exploits and were happy to work for him, as long as it paid well. But he didn't have the money to pay for the 200 men. So he offered up titles for massive estates in Florida for their service. This would have been a pretty sweet deal, were it not for the small caveat that McGregor owned none of the land and never would. This fact didn't stop him from raising money by selling land he didn't own in the soon-to-be-conquered Florida. Once McGregor had conquered the towns, he didn't bother claiming land or setting up counter defenses for an inevitable counterattack. Nah, his vibe was more sitting around drinking and essentially doing nothing. Consequently, out of sheer neglect and utter laziness, McGregor never paid his mercenaries. The last thing these mercenaries saw as they awoke one fateful day was the back of McGregor's ship as it sailed away with all the pillaged gold and goods. Classic Gregor. McGregor's next adventure saw him attempting to take control of Panama in 1818 when he took around 500 men to Portobello. They took the city without a fight, which allowed Sir Gregor to rule as king over one of the most prosperous cities ever. And roll credits. Just kidding. Instead of continuing his campaign while his troops were fresh off a sweet victory, McGregor just kind of lounged around, drinking and relaxing with no additional defenses set up in the city. Inevitably, the Spanish showed up and launched a counterattack for which Gregor had no plan to defeat. So he courageously jumped out of a window and fled on foot, leaving his troops behind. McGregor did return a year later and was able to retake the stronghold. But he fell into his classic post-war drunken stupor. And the Spanish launched another counterattack, forcing him to run away once again and leaving his remaining men to be captured by the Spanish and put to death. Starting to think this guy shouldn't be in charge of anything. McGregor became a wanted man based on his many failed siege attempts and the fact that he had driven so many of his troops to the deaths. Desperate, alone, and in hiding, McGregor began traveling along the mosquito-infested Nicaraguan coast. Local tribes descended from enslaved African and Native Americans ran things there. And one of these tribe leaders, King George Frederick Augustus, struck up a natural rapport with McGregor after a day's long drunken bender because nothing brings two dudes together like entirely too many beers. Augustus ended up trading 8 million acres of tribal land for McGregor's rum and jewelry. While the tribesmen doubted a viable use for the land could be found, McGregor had already thought up his latest grift. McGregor now found himself the owner of more land than the entire island of Hawaii. The only problem was the land was pretty useless, to everyone but a master con man, that is. To turn this newly acquired land into a steady source of income, McGregor invented a whole new country called Poyais. Using his ownership of the land as proof of his claims, McGregor got to work on hyping up the non-existent country. He dubbed himself His Serene Highness, Prince Gregor McGregor, and returned to London with his wife. Despite all that running away we talked about earlier, McGregor was still known as a war hero. So nobody questioned his claims that Poyais was a real country. That only sounded too good to be true. Fake offices were built in London to legitimize the con. He claimed Poyais had rivers of gold and the soil was fertile enough for three harvests a year. After concocting a bogus settler's guidebook and taking out ads in local papers, McGregor was able to successfully bilk over 500 investors. Man, where did he put in that guidebook? McGregor's biggest con was a runaway success for him. He managed to convince several hundred settlers to purchase land in his make-believe country. Instead of being greeted by the beautiful utopia McGregor had promised, the settlers were greeted with harsh jungles and desolate swamps. McGregor had been so convincing with his con that the settlers believed that they had made a wrong turn and were searching for Poyais in the wrong place. They sailed up and down the Mosquito Coast hoping to find their paradise. What they found instead was more mosquitoes. After being forced to settle amongst the swarms of blood sucking bugs, more than 200 settlers, including families and children, succumbed to malaria and yellow fever, which is just the cost of doing business for a guy like McGregor. Some fortunate souls were rescued by passing ships. And although they shared horror stories about McGregor's indefensible grift, those stories fell upon deaf ears and the Poyais con continued unabated. Eventually, word of the Poyais scheme began to spread so much that naval ships started to intercept potential settlers to save them the hassle. As word of his grift continued to spread, people became more and more aware of McGregor's egregious lies. But recognition of the scheme was not enough to stop it. McGregor did such a good job at swindling investors that the con lasted from 1822 until 1837, just a shade over 15 years before people wised up. And even though the jig was up, we'll probably never know just how many lives were affected by McGregor's lies or how many people he doomed to an untimely demise on the Mosquito Coast. McGregor was able to use the money he obtained scamming the British to move to France and start the same con all over again with a new audience. Luckily, French authorities caught on to the con much faster than anyone else, and McGregor was finally arrested. In a stunning display of justice not being served, McGregor made a compelling case of blaming his French collaborators and wound up only serving six months in a French prison, Merde. Despite his many crimes, both against the crown and humanity, McGregor was acquitted for his wrongdoings. The rest of his life was unjustly quiet. After his wife passed away, McGregor moved back to Venezuela, where he was given his general's pension and lived peacefully until he shuffled off to the great con in the sky in 1845 at age 58. So remember, crime doesn't pay, except in this specific instance where it makes you a legend. So what do you think? Was McGregor a charming rogue or a despicable hustler? Let us know in the comments below. And while you're at it, check out some of these other videos from our Weird History.