Gregor MacGregor: The Most Successful Conman in History,Biography of gregor macGreger,Gregor MacGregor

                                                                       

                       Gregor MacGregor: The Most Successful Conman in History

Charles Ponzi. Bernie Madoff. Billy “Fyre Festival” McFarland. History is littered with the misdeeds of conmenwho pulled the wool over the public’s eyes and made a killing. Some, like Frank Abagnale - the model forLeonardo Dicaprio’s character in Catch Me if You Can - pulled off cons so big they’vebecome legendary. But not even Abagnale could compete with oursubject today. Gregor MacGregor was many things: soldier,pirate, pathological liar. He was also the man who pulled off the biggestcon in history. In 1821, MacGregor arrived in London withtall tales of a new Latin American nation where fortunes could be made.

 Using his deadly charm, MacGregor managedto not only swindle banks, investors, and ordinary people out of the 19th Century equivalentof billions of pounds, he indulged in fabrications on such a colossal scale that even Europe’sgovernments were fooled. But how did this Scottish nobody create acon so big it swallowed an entire continent? Join us as we explore the life of Gregor MacGregor,the most amoral adventurer to ever live. Birth of a ConmanWhen he came to tell the story of his birth many years later, Gregor MacGregor would neverlet two details remain the same. He was born into high Scottish nobility. He was descended from the legendary outlawRob Roy. His ancestors were adventurers who foundedScotland’s doomed colony in the Darien Gap.


The odd thing was, he needn’t have bothered. Gregor MacGregor’s background was interestingenough even without his tall tales. Born on Christmas Eve, 1786, MacGregor camefrom, well, the MacGregors, a Jacobite Clan that had only just been relegalized after100 years as outlaws. While his dad wasn’t the chief, as MacGregorwould claim, his family were still notable. His grandpa had been an officer in what wouldbecome the Black Watch. His father was a ship captain. In short, young MacGregor had action in hisblood. And in 1803, when MacGregor was only 16, thatblood would drive him to seek adventure in the British Army. As luck would have it, 1803 was the year theNapoleonic Wars broke out, and MacGregor was hurriedly posted to the island of Guernseyto defend against French invasion. But that invasion never came. Instead, MacGregor wound up living a deeplyunadventurous life of waiting around. Not that his time on Guernsey was all a waste. It was while on assignment that MacGregormet his first wife. Maria Bowater was the sort of catch youngenlisted men used to dream about.

 Her father was an admiral, her family memberswere MPs. Oh, and they were absolutely, stinking rich. In no time at all, MacGregor had charmed hisway into marrying her, much to the horror of her family. No sooner had they tied the knot then MacGregorwas using his wife’s money to buy himself the rank of captain and get transfered downto Gibraltar. But while the weather may have been niceron Spain’s southern tip, life was still boring. For the next four years, MacGregor did nothingbut stand around, waiting for a French fleet that never came. Then, in 1809, just as MacGregor was planningto give up and return to Scotland, excitement finally arrived. The year before, Napoleon had invaded Spain,engulfing the whole of Iberia in the Peninsular War. Sensing a chance to give Napoleon a blackeye, the British decided to intervene. And that’s how Gregor MacGregor found himselfin Portugal fighting Napoleon’s forces.

 Yet even in the heat of combat, MacGregorcouldn’t settle. In October, he sold his rank of captain anddeparted the British Army for the Portuguese one. But by May, 1810, he’d also got bored ofthe Portuguese and resigned again. Come summer, 1810, MacGregor was back in Scotland,feeling as unfulfilled as ever. But he was no longer merely “Gregor MacGregor.” On leaving the Portuguese Army, MacGregorhad started telling people he’d been knighted for his service, and was now “Sir MacGregor”. It was a stupid lie. A dumb, egotistical little lie that shouldn’thave changed anything. Yet change things it did. When people didn’t question it, MacGregorrealized just how easy lying about even huge things really was. It was a revelation that would soon take theyoung man to some very bizarre places. Life with the LiberatorIn April, 1812, a ship pulled into port near Caracas, Venezuela, and disgorged a slenderScot in his mid-twenties. It had been two years since MacGregor hadleft Portugal disillusioned, and much had happened.

In 1811, his wife had died, and his in-lawshad cut him off financially. So MacGregor had left Britain, in search ofsomething - anything - that would keep his mind occupied. Luckily, 1811 wasn’t short of opportunitiesfor a would-be adventurer. That year, Venezuela had declared independencefrom Spain, kickstarting the South American Wars of Independence. So MacGregor had decided to get involved. No sooner had he landed than then-Republicanleader, Francisco de Miranda, had appointed him a cavalry officer. But it’d be an even bigger name in Caracassociety that MacGregor would soon get involved with, thanks to his 1812 marriage to JosefaAntonia Andrea Aristiguieta y Llovera. Josefa, you see, was cousin to none otherthan Simon Bolivar. Not that his newfound connection would immediatelywork out well for MacGregor. Just months after his marriage, MacGregorwas in flight, running for safety as the First Venezuelan Republic fell to Spanish forces. Francisco de Miranda was captured, while bothMacGregor and Bolivar only escaped - heading in opposite directions - by the skin of theirteeth. And so began the period of Gregor MacGregor’slife where he kept crossing paths with the greatest figure in Latin American history,only for it all to keep going horribly pear-shaped. In 1813, for example, MacGregor volunteeredin the New Granada army, only to be assigned to a remote border town and miss Bolivar’sAdmirable Campaign and founding of the Second Venezuelan Republic.

In 1814, the two both wound up in Cartagenaafter the Second Republic fell, but Bolivar was forced into exile while MacGregor gottrapped in the siege of the city. Finally, MacGregor reconnected with Bolivarin Haiti in early 1816 and joined his latest campaign. It was a campaign that would nearly cost MacGregorhis life. By now, most of Venezuela was back under Royalistcontrol. Bolivar’s plan was to land men at strategicpoints along the coast, then coordinate a mass uprising. Put in charge of 600 troops, MacGregor wasquietly dropped at Ocumare. Unfortunately, the plan instantly fell apart,Bolivar was forced into retreat, and MacGregor and his men were left standing on the shore,their mouths dangling open as their ride disappeared. They were trapped in Royalist territory, over300km from the nearest Republican stronghold. They had no boats, limited ammunition, even-morelimited provisions, and were surrounded by swampland. At that moment, it must’ve seemed to the600 men like death was a certainty. They hadn’t counted on MacGregor’s talentfor self-preservation. In a remarkable feat of leadership, MacGregorled his men on a march right through Royalist territory, executing innumerable brilliantmaneuvers to keep the enemy at bay. He tricked the Spanish troops into walkinginto swamps.

He had his men charge blockades on foot andpunch right through. It was like watching LeBron James lead ElmerFudd around a basketball court, with the dimwitted Royalists fumbling every play while MacGregorran circles around them, laughing. And yes, as far as we know, we are the onlyYouTube channel delivering history via Space Jam 2 analogies. You’re welcome. After weeks of running battles, MacGregorfinally led his men into the safety of a Republican town. When news leaked of his 300km trek, the Republicancamps exploded. MacGregor became a hero overnight, his namecelebrated across the continent. Suddenly, everyone wanted to serve under him,the guy who’d married into Bolivar’s family, and then out-Bolivared Bolivar. But, sadly, this isn’t a video about GregorMacGregor, revolutionary general. It’s a video about Gregor MacGregor, conmanextraordinaire.

Those soldiers all clamouring to serve underhim didn’t know it yet, but MacGregor would soon lead countless of their number into earlygraves. Third Time’s the Charm... In the wake of MacGregor’s daring escapefrom Ocumare, Bolivar personally awarded him the Order of Libertadores - hopefully whileshuffling awkwardly and mumbling “sorry I abandoned you back there, bro.” But MacGregor was disappointed. He hadn’t gone through hell just to geta shiny new medal. No, he wanted a promotion. A raise. Something to show the world he was a hero. If Ocumare wasn’t enough for his cousin-in-law,MacGregor would just have to go one bigger. That fall, mercenaries up in Pittsburgh beganto whisper about a Scottish man doing the rounds, hiring people for a private invasionof Spanish Florida.

The Scot was a Portuguese knight, a Venezuelanhero. More to the point, he was very generous. Anyone who joined him was being given titlesto huge estates in Florida. For the rough and tumble men of Pittsburgh’sdive bars, it seemed like a no-brainer. Which is how in June, 1817, MacGregor wasable to sail for Amelia Island, Florida at the head of 200 mercenaries. There was just one minor catch. MacGregor didn’t actually own the land he’dbeen dishing out to his private army. But, hey, while spoil a good invasion, right? Not when everything was going so well. And it really was. When the only Spanish garrison on the islandsaw all these armed Americans, they assumed it was the head of a full-blown US force andsurrendered. Now all MacGregor needed to do was press hisadvantage, take a few more forts, and he’d soon have another victory to rival Ocumare. But that didn’t happen. Instead, MacGregor declared Amelia Islandthe Republic of East Florida, and then simply settled in to enjoy getting drunk and sunninghimself.

 For MacGregor’s men, this must’ve beena “what the-?” moment. Then MacGregor started paying them in Republicof East Florida dollars he’d made himself and it became a “Whaaa-?!” Finally, one morning in September, the mercenariesawoke to find MacGregor had taken the ship and remaining money and simply sailed away,leaving them to their fates. At that point, they probably couldn’t evensummon a squeak of surprise to show how they felt. Following the Florida failure, MacGregor badlyfell out of favor with Bolivar. So he tried again. In 1818, MacGregor sailed back to Britain,hired 500 more men, and this time tried to conquer Panama. Landing a force of 200 at Porto Bello, hetook the city… ...and then went straight back to loungingaround in the sun, drinking rum and failing to do anything that might stave off a potentialSpanish counterattack. This last bit proved important when the potentialcounterattack became an actual counterattack and MacGregor was forced to flee, once againleaving his mercenaries to their fates.

By now, the Scot was starting to look lesslike the capable general of Ocumare, and more like a shallow egotist who’d just happenedto get lucky. But his name still carried enough shine forMacGregor’s surviving men to follow him on one last invasion. In October, 1819, MacGregor landed outsidea Royalist holdout on Venezuela’s coast. It was the exact same checklist as AmeliaIsland and Porto Bello: MacGregor takes city? Check. MacGregor gets drunk rather than organizedefenses? Check. When things go south MacGregor sails awayand leaves his men to their fates? Double check. This time, those fates were particularly gruesome. After the Spanish retook the city, they linedup all of MacGregor’s surviving mercenaries and had them shot. In the aftermath of MacGregor’s third colossalscrew up, Simon Bolivar didn’t so much throw the book at him as crush him beneath an entirelibrary of disapproval. Bolivar declared his cousin-in-law a traitor. He issued a decree that any Venezuelan whosaw MacGregor should kill him on sight. But while this was the end of MacGregor’stime as a revolutionary warrior, it wasn’t the end of the man himself. When he resurfaced, it was going to be witha con that would go down in history. The Con is On Sprawling along the Caribbean coasts of modern-dayNicaragua and Honduras, the Mosquito Shore is exactly as unappetizing as its name suggests.

It’s a hot, wet, desolate place where lifeis cheap, disease is rife, and mosquitoes omnipresent. In April, 1820, Gregor MacGregor hopped offa boat and vanished into the mangrove forests of this tropical Hell, desperate to lose himself. By now, it wasn’t just Bolivar who wantedhim dead. The Spanish, the Americans, the British…all, for varying reasons, had MacGregor’s name on a hit list. In the movie of MacGregor’s life, this wouldbe the low-point, the part where all seems lost. But you know what always comes after the lowpoint in any movie script? The part where the hero triumphs. While hiding on the Mosquito Shore, MacGregorcame into contact with one of the local tribal leaders, a guy who styled himself King GeorgeFrederick Augustus. Being a natural charmer, MacGregor got theguy drunk and spent a few days partying with him. By the time he emerged from the king’s hut,weary and hungover, MacGregor was clutching a title deed to 8 million acres of triballand.

This piece of paper would become the basisfor his audacious next move. Back in MacGregor’s native Britain, thenation was gearing up for the coronation of George IV. There were street parties. Dignitaries from all over the world. In fact, there were so many dignitaries no-onenoticed when one arrived from a country that didn’t exist. His Serene Highness Gregor MacGregor the First,Sovereign Prince of the State of Poyais and its Dependencies, and Cacique of the PoyerNation arrived in London in summer, 1821. Just like with MacGregor’s fake knighthoodin 1810, no-one questioned his absurd new title. To understand why, you have to remember whenthis story is set. In 1821, a whole bunch of new nations hadjust exploded into existence: Mexico, Gran Colombia, Argentina, Chile, Paraguay, Peru.

 For Londoners, it wasn’t much of a stretchto believe Poyais might be among them. Especially when the Poyais envoy was relatedby marriage to Simon-freaking Bolivar. But MacGregor did more than just trade onhis connections to fool people. Under the pseudonym Thomas Strangeways, hepublished a guidebook to Poyais, detailing the nation’s government, its geography,its climate, its architecture. This was serious imagination, something Tolkeinwould’ve been proud to write, and it was shot through with glimpses of a utopia. There was the soil, so fertile it could supportthree harvests a year. There were the riverbeds, where lumps of goldlay along the banks. And there was the fact that, uniquely forCentral America, Poyais had no tropical diseases. Trust us, that last one will soon seem bitterlyironic. But why did MacGregor go to all this troubleto invent a fake country? For an answer to that, you need to look toLondon’s Scottish communities. That same summer, the Poyais envoy began visitingthem. He was offering them an opportunity, he said. An opportunity not just to better their ownlives by moving to Poyais, but an opportunity to establish Scotland’s first viable colony.

A chance to make their country into a globalplayer. All they had to do, Gregor MacGregor toldhis fellow Scots, was to buy one of these plots of Poyais land he was selling. Fertile land that would set them for life. Faced with such an offer, who could refuse? The BubbleBy the fall of 1822, interest in Poyais was running rampant. The first boatload of Scottish settlers hadjust departed for the country, and a general bubble in Latin American securities was expanding. So when MacGregor asked a bank to underwritePoyais bonds, they simply nodded and handed him £200,000. Using that money, MacGregor opened Poyaisconsulates across Britain, adding to the scheme’s veneer of legitimacy. For MacGregor, these were the salad days;a phrase which means the heyday of something, which is an odd choice when you consider howboring salad is. By winter, investment in Poyais bonds hadgenerated over a billion pounds in today’s money. And MacGregor was still selling land to gullibleScots! The second boat of settlers departed in January,1823. But there’s one problem with dispatchingboatloads of settlers to a non-existent country. What do you do when they finally arrive? Well, let’s find out.

 In November, 1822, the first ship reachedthe Mosquito Shore. As the boat approached land, the Scottishsettlers all donned their fanciest outfits, and fired the gun so a Poyais boat would comeout and guide them to the capital. Instead, the gunshot echoed across the emptywaters and mangrove swamps, answered only by deafening silence. At first, the settlers assumed they must’vemade a navigation error. So they all had their stuff unloaded ontoa deserted stretch of coast, and sent the captain off to find Poyais. It’s worth noting that these were not young,hardy types desperate for adventure. Most of those caught up in the Poyais schemewere older folks looking for an easy retirement, or families with young children. Surviving on a deserted stretch of tropicalshore was definitely not within their skillset. In March, 1823, the second ship joined thestranded settlers. Incredibly, everyone still assumed their navigationwas off. Even when the captain of the first ship returnedand said “so, I’ve sailed all up and down this coast and there’s no Poyais,” theytold him, “err, obviously there is.

 Duh. Try again.” So off the captain went again. And the now hundreds-strong crowd of settlerssettled down to wait again. That same month, a hurricane battered theMosquito Shore, destroying supplies, and wrecking the remaining ship. Then the rains came. Thick, heavy, endless rains that left thesettlers soaked. Finally, in the wake of the rains, came themosquitoes. If you’ve ever been to the tropics in rainyseason, you’ll have seen just how thick the air can get with mosquitoes carrying yellowfever and malaria. On the deserted shore, the insects mobbedthe unprepared settlers, biting them, infecting them. One by one, the abandoned Scots began to die. Babies passed away in their mothers’ arms. Elderly women died, wracked with malaria. Of the 200 or so Poyais settlers who reachedthe Mosquito Shore, it’s estimated over two thirds were killed by tropical diseases. It was a massacre by neglect. A death sentence as sure as a firing squad. The only reason anyone survived is becausea ship from British Honduras just happened to pass and alert the colonial authorities. For the rest of 1823, the Royal Navy was overwhelmedevacuating the survivors and intercepting ships headed for Poyais. By the year’s end, they’d stopped fivemore settler ships, each carrying hundreds of people.

 Had they reached the Mosquito Shore, it’slikely the death toll of the Poyais scheme would’ve topped a thousand. Back in London, news of the disaster firstbroke in October, 1823. Immediately, lots of very angry people beganlooking for Poyais’ charming envoy. But they were too late. MacGregor had fled England just before thestory arrived, taking as much of his ill-gotten cash as he could carry. It was a horrific denouement to the wildestcon ever pulled. Unbelievably, it still wasn’t over. Gregor MacGregor wouldn’t be done with thePoyais scheme for another fifteen years. No Bad Deed Goes UnrewardedFrom 1823 to 1838, MacGregor pulled his Poyais con again and again. Incredibly, he never faced any serious punishmentfor it. Even after the harrowing tale of the survivorsgot out, no-one in Europe could accept Poyais didn’t exist. MacGregor had simply lied too big. In the same way our brains wouldn’t be ableto process the revelation that, say, Hawaii wasn’t real, people in the 1820s just couldn’tcomprehend the idea that Poyais was fictional.

When MacGregor settled in Paris, the Frenchgovernment even made him an advisor on Latin American affairs! This despite MacGregor restarting his fakebonds scheme in France. Although the scheme itself was busted in 1825,MacGregor successfully blamed his French partners, and again got away Scot free. He even returned to London and got more bondsunderwritten for £800,000. While no investors bit this time, it wasn’tbecause of the tragedy on the Mosquito Shore. It was because the Latin American securitiesbubble had just burst, and no-one wanted to risk another. For the next few years, MacGregor hawked hisscheme up and down Britain. While he never again hit the big time, healways had just enough money coming in to keep the fiction going, to keep people believingin Poyais. Finally, in 1838, MacGregor’s wife Josefadied. Suddenly alone in gloomy Britain, the conmanseems to have at last given up on his con. That October, MacGregor got on a boat andsailed back to Caracas.

 He never mentioned Poyais again. So… this is the moment, right? The moment when MacGregor finally gets hiscomeuppance. I mean, he’s headed back to Venezuela, thevery place Simon Bolivar left orders that he be killed on sight. If you’re hoping for a moral end to thisstory, best switch off now and construct one in your own head. See, Bolivar had died all the way back in1830, by which time he incredibly unpopular. With Bolivar’s name now mud, everyone waslike “I mean, do we really need to kill this random Scottish dude?” So they let MacGregor land. They even let him request an audience withthe government. At which point, Lady Luck dropped an utterlyundeserved gold nugget right into MacGregor’s lap. Remember Ocumare, the one time that MacGregoractually acted like a hero? Well, General Carlos Soublette did.

 He’d been under MacGregor’s command duringthat mission, and seen the conman at his best. Since he’d never followed MacGregor to Florida,or Porto Bello, or even heard of Poyais, he had no idea of MacGregor’s true character. And now Soublette was a member of Venezuela’sgovernment. When he saw MacGregor, he basically let outa cry and threw his arms around him. That was how, in 1838, Venezuela came to reinstateGregor MacGregor’s rank in its army, hand over twenty five years’ back pay, and givehim a generous pension. For the next seven years, MacGregor livedin Caracas, wealthy, happy, and respected by all. He finally died a peaceful death on December4, 1845, without having ever repented of his cons. Sometimes, life really is unfair. Today, it’s estimated that, between thePoyais scheme and all those times he abandoned his men, Gregor MacGregor was responsiblefor the deaths of 500 people. Yet even though he never got his comeuppance,his story offers us all an excellent moral lessons. It’s easy to fall into the trap of assumingthat the world is fair. That maybe bad things sometimes happen, but- in the end - everything will always balance out. The tale of Gregor MacGregor laughs in theface of this. Here was a man who treated other people asdisposable trash, only there to fuel his own fantasies.

 A man who sacrificed literally hundreds oflives to the God of his ego. And he never tasted justice for even a singlesecond. Unique among figures we’ve covered, MacGregoroffers us a bleak but necessary warning. Sometimes, good doesn’t triumph. Sometimes, the happy, wealthy, respected peopleare the ones who have caused untold suffering. Gregor MacGregor may be long dead, but therewill always be others out there like him, charming and amoral. If his life shows us anything, it’s thatwe should always be on the lookout for these people. Even when they seem to be the most respectabletypes you could ever hope to meet.