Richest pirates in history. Y Blackbeard, probably the most notorious pirate in history, surprisingly ranks poorest among the wealthy pirates on this list, though he still made bank. Before the beard, he was known as Edward Teach, a small English chap born around the 1600s. History's forgotten the exact year, so we'll just go with it. In the same sense, not much is known about Little Eddie before he got his first facial pube, so let's fast forward a bit. In the early 1700s, the Caribbean was really going through it as the English, the French, and the Spanish duked it out for territorial control and dominance over trade routes in and around the Americas. One side effect of this conflict was the hiring of privately owned ships to attack and capture other ships. It was like a big game of rock paper scissors, but it was just guns, guns, guns. These private guns for hire were called privateeers and were given written permission from their respective crowns to plunder and pillage any and all enemy ships to their liking. After all was said and done and the three crowns made peace in 1712, these privateeers who were used to being able to just ransack whoever they wanted to for all they were worth were now out of a job. Oh well, legally speaking anyway. In fact, most privateeers just kept up their shooting shiny ship shenanigans without a shadow of shame. And this is where the golden age of piracy began to peak and where most of these salty dogs made their fortunes. Eddie Teach was once such a privateeer, having served under the English crown during Queen Anne's War in his youth. Around 1716, Eddie Spaghetti took an opportunity to make his fortune, joining a crew under renowned English pirate Benjamin Hornigold. After Teach had seized several small enemy ships and proved his worth, Hornold was all nice and Tee was given more command. Eventually, Hornold was ousted as captain after his refusal to attack fellow English ships that were just brimming and throbbing with gold. He was given a full pardon from the English crown and retired in peace. Teach was elected as the new captain and was thrilled at the new venture as he could now do things his own way. Almost immediately after his promotion, the crew had captured the ironically named French ship la meaning harmony in English. Now sure, one can expect a few casualties when a ship is absolutely reamed from both sides with cannon fire. But this was a slave ship and this is how slave ships were packed. Surrendering immediately, the ship was taken and any surviving slaves were set free on a nearby island to be recaptured later. Okay. The brand spanking new vessel was given a makeover, having 40 cannons slapped right on that thing. The ship was repurposed as Teach's flagship and renamed to the Queen Anne's Revenge. Now an absolute powerhouse, Teach took to the seas to seek his fortune. His most prominent tactic, of course, was intimidation. Not only did he have a brand new ship well equipped to rip any opposing vessel 40 new but his menacing appearance alone would surely make you pucker your own in fear. As his nickname implies, Blackbeard had a long jet black beard entwined with various lit fuses. This gave him a terrifying demonic look which was quickly offset by the smell of burning hair. But if you were sailing your sloop and saw this coming up in your rearview mirror, you just about a brick. For a couple years, Blackbeard terrorized the Carolinas, seizing ships and taking hostages. But across the Atlantic, English King gentleman dude George I was kind of getting sick of pirates. He offered free pardons to anyone willing to throw in the smelly towel and a free rope necklace to anyone that didn't. Blackbeard took the offer, but fell right back into piracy when the opportunity presented itself, which was immediately. Well, the governor of Virginia took matters into his own hands and assembled a team of pirate hunters to cut down the callous captain. In the wee hours of the morning on November 22nd, 1718, Blackbeard was ambushed by the Royal Navy and his crew was slaughtered. Blackbeard himself sustained 20 stab wounds and five gunshot wounds. Although short-lived, Blackbeard's notorious pirate career amassed a pretty penny. It's estimated that his plundering racked up about $240,000 or about $18.5 million adjusted for inflation in 2025. In the end, Blackbeard's head was severed and his body disrespectfully dunked in the drink. His melon was mounted as a warning to any and all future pirates, but an invitation to some. Born in the American colony of Massachusetts, Captain John Hollyy began his sailing career as a privateeer for the English crown in 1704. He started off by praying on French fishing fleets in the North Atlantic, but eventually preferred attacking Spanish ships near the Canary Islands off the coast of West Africa. This didn't last long as his letter of mark, the English monarchy's permission slip to raid enemy ships, expired the very next year. Unable to legally loot and plunder, Captain Hollyy turned to piracy and sailed further east into the Indian Ocean. The goal here was to intercept Mughal Empire treasure ships. But after several months of sailing around with no booty to show for it, crew morale was at an all-time low. This led to the aggravated crew jumping at any opportunity to score some simoleons. One day, a Dutch ship passed by Holly and his crew looking very vulnerable. Hollyy, unwilling to attack and anger any European powers, shrugged it off and just kept chugging along. This elevated crew status from peeved to piss, and Hollyy was voted out of office, which is something the pirates did. If they felt like the guy in charge just wasn't up to snuff, they could just vote him out democratically or metallically, depending on the crew. Hollyy was metaphorically stripped of his captain duties and the crew took it upon themselves to attack the Dutch ship, expecting it to be some pushover merchant equipped with nothing more than a singleshot pistol and a few yiatas. Turns out not so. The Dutch ship in fact had several large cannons and a surplus of yiatas. The Dutch fired a warning shot at the approaching crew and it was wellreceived. The rogue cannonball managed to slightly injure the guy at the helm and took out a few armaments at the same time. The crew got the message and did a 540 out of there, immediately reinstating Holly as captain with a collective, "My bad," which it kind of was. On the next trip to shore, Captain Holly disbanded the crew and formed a new, less mutinous one. Still seeking his fortune, John Holly found himself in the Red Sea in 1707, where he encountered not one, not two, but five heavily armed English warships. What's the move, Captain? We move forward. Sir, we're heavily outgunned and outmanned, don't you think? Did I stutter? Well, yeah, you kind of did. I said forward. Okay. Damn, I spit in my face. Holly and his crew stared down five massive warships, each one more English than the last. Seeing such a poulry crew, the English warships said frigot and inexplicably retreated. In the confusion, Holly and his crew managed to capture two of the five warships before the rest completely buggered off. The crew returned to shore in 1708 to celebrate their well-deserved victory. But Hoy would never return to the sea. The two warships along with their cash and cargo and various other small loot from Hollyy's pirating career are valued at around $19.4 million in today's money. It's just too bad that shortly after making port, all three of John Hoy's ships were ripped apart by a hurricane and sank. He lost his fortune, but at least he still had his health. Just kidding. He died of a fever shortly after the storm at the age of 45ish. Sure, you can face five gallions strapped to the keel head on, but god forbid your body temperature goes up a few degrees. Yep, that Captain Morgan, the one responsible for many a college headache and morning walks of shame. But before he got a leg up on the rum business, he was quite the headache to the Spanish in the mid600s. Born Henry Morgan around 1635 in Wales, fate would bring this young fellow to the Caribbean of all places. It's unknown exactly how he got there. He could have been part of an expedition, served as an apprentice. Who knows? All we care about is that it's the 1660s and Morgan is now in the Caribbean setting up his home base in Jamaica, which was recently captured by the English. Around this time, Jamaica was developing into a reputable trading hub, revving up its plantation business and seeing roughly 1500 privateeers spend their spoils on the local economy. Morgan sailed under English privateeer Sir Christopher Ming as a captain, and together the crew ransacked Spanish settlements in cities across the Caribbean and Central America. Jamaica did eventually come under threat of invasion from the smelly Spanish. So, Captain Morgan was promoted to the much less marketable Admiral Morgan and was put in command of 12 ships and about 700 men. Through his letters of mark from the English crown, Morgan had permission to attack Spanish and Dutch vessels at sea. The problem though is that ships hold significantly less goods for the stealing than say an entire town. Though he was not legally cleared to do so, Morgan began attacking Spanish strongholds between the years of 1667 and 1671. His exploits netted him millions in Spanish bribes to spare towns and cities. And by the time he attacked Panama City in 1671, Morgan had over 30 ships at his command and hundreds of crew members, by far the largest across the Spanish main at the time. Now, in order to take down this Panama City where the gold coins gleam and the girls got titties, Morgan sent a well-armed and well-trained party of 300 men, which clashed against roughly 1,600 inexperienced Spanish soldiers. And to say that the Spanish got their slapped would be an understatement. The Spanish forces saw between 400 to 500 casualties with Morgan only losing 15 men. Panama's governor, now cornered, decided that instead of allowing Morgan to take the city, he would instead burn it to the ground. After Morgan claimed his victory, the city erupted in flame as the surviving Spanish troops set fire to the city. The blaze lasted until the next day, where Morgan and his crew plundered whatever goods weren't burnt to a complete crisp. Uh, they burnt the spices. They burned the gold. They burned me. Since what he did was technically illegal, Morgan was arrested, but was never charged with any crime and was instead formally kned for his undying loyalty to the English crown. He did make his way back to Jamaica and served in a government role with the goal of eradicating piracy from the Caribbean waters, but he eventually fell out of power and fell onto the bottle, becoming a depressed alcoholic. In his final years, Morgan made sizable investments in plantations, owning three along with 131 slaves to work them. On August 25th, 1688, Henry Morgan died of complications from his heavy drinking at the age of 52. Across his very successful pirating career, Morgan's total captured booty is estimated to be worth around $19.6 million, adjusted for inflation. Although he died a drunk, his spirit lives on in your local alcohol store as an ironic proof of his spicy exploits. Remember to pour one out for the captain who was really an admiral. Jean Flurry's story is one of luck rather than tactic. This time we're going to jump back to the 1520s, right about the time that Arnan Cortez had finished steamrolling the Aztec Empire. With seemingly endless spoils for the Spanish crown, Cortez sent three loaded treasure gallions back to Spain. And they almost made it back home. Almost. Enter Jean Flurry, a French privateeer on the lookout for any Spanish ships who need a sinking. Stationed in Portugal during the four years war, which pitted France against the Holy Roman Empire as well as Spain, Jean Flurry was in the perfect position to intercept Spanish and trade resupply ships. In early 1522, the three Spanish treasure gallions with gold blowing out their poop decks were spotted on the horizon on the home stretch to Spain. Jean saw these small Spanish fleet and said, "No way, Jose." but in French. Flurry unleashed a flurry of cannons and quickly overtook two of the three ships before they could reach safer waters. Content with capturing the ships, Jean had no idea what he had stumbled upon. Below deck, the ship's holds were crammed and jammed with mountains of stereotypical pirate treasure. Stacks of glistening gold, glittering jewels, exotic animals, and various rarities for the taking. Jean Flurry hit the jackpot, and with the score of a lifetime, he could have retired as a wealthy man. But that's for quitters and real men know that the grind never stops. With knowledge of Spain's incredibly stacked ships, Flury set out with his own fleet to try his luck at chasing that high. He and his crew managed to capture over 30 Spanish ships within the year, but couldn't find a fortune like the one before. The Spanish just about had enough of the Frenchmen and eventually captured, tried, and hanged the greedy little bastard in 1527. Flurry's amassed wealth was heavily carried by his first score. But nonetheless, his pirating career netted him about $ 47.1 million. But as Flurry found out, you can't take it with you. Big Black Bart was one of, if not the most successful pirate during the Golden Age of Piracy in terms of vessels captured. The first detailed records of Blackbart, aka Bartholomew Roberts, dates back to 1719 when he was the second maid on a slave ship stationed off the Gold Coast of West Africa. It was here that the ship was captured by Welsh Captain Howell Davis. Roberts and surviving members of the crew were forced to join Davis's ranks. But Davis found some value in Roberts, not only because he was a skilled navigator, but also a fellow Welshman. When you come across someone who speaks your native tongue, you're going to bro it out, which is what happened. Hello. Hello. Davis and Roberts would have long conversations in their funny little language that none of the other sailors could understand. Through these little chitchats, Davis convinced Roberts that yo ho ho, a pirates life was for him. Roberts was hesitant at first, but the idea grew on him when he realized that a life of piracy could at best lead to riches and at worst provide a short but adventurous life, much better than being a wage slave to the man. Take that, capitalists. Instead, Roberts pulled himself up by his bootstraps and found a way to steal livelihoods away from hardworking folks. As such an inspirational captain, Roberts really looked up to Davis. But then Davis dung got shot by the Portuguese. Roberts, recognized as a close companion to the now dead Davis, was elected as the new captain, much to the dismay of the Portuguese, who very quickly learned a demonstrative definition of the word revenge. Roberts, now in command, really fell into the role of a pirate captain. He began capturing ships left and right, and on an expedition to Brazil, encountered a large fleet of 42 Portuguese ships. Roberts was able to locate the richest ship in the fleet by using the simple tactic of asking nicely. And which one has the most gold on it? Oh, well, it's that one right over yonder. Oh, thanks. Roberts continued his successful spree of ship stealing for the next few years with his crew growing fiercely loyal. To maintain order and morale, Roberts developed his own pirates code, a set of agreements and laws that would be upheld by every crew member, bringing law to lawless men. Roberts was also one of the early adopters of the infamous Jolly Rodgers skull and crossbones black flag. Flying the Jolly Rodger was a great way to tell your targets that was about to hit the fan should they choose to stay and fight. Most didn't. In fact, in 1720, Roberts and his crew made their way up to New Finland, entering a harbor with their black flags whipping in the wind. Any and all surrounding ships crews abandoned their post and fled. Roberts took the town, 22 merchant ships, and 150 fishing vessels without firing a single shot. Across his entire pyatical career, Roberts yunked over 400 ships, making him the most successful pirate of the Golden Age. His plunder is valued in the ballpark of 48.2 million. His career was successful, but all good things must come to an end. On February 10th, 1722, a British Royal Navy ship ambushed Roberts and fired a volley of grapeshot broadside. Grapeshot, if you're unaware, were basically giant grenades. Several small iron balls a few inches in diameter, densely packed in a canister designed to take out enemy crewmen. Well, poor old Roberts caught a ball right in the throat as he stood on deck, killing him instantly. It was 39. As you can probably tell, active pirate careers were pretty short. Most died right when the getting was good. A simple rogue cannonball, splinter of wood, or a stray cough could cut down a pirate where he stood. And Captain Thomas 2 was no exception. Beginning his privateeering career at the tail end of the 17th century, Tommy 2 was commissioned to ravage a French factory on the coast of West Africa. Sailing across the pond from Bermuda alongside one Captain George Dub, both men had a lot to do. But mother nature had other plans. Glad that wasn't us, right? Young want to be pirates. Okay. Sure. Okay. Sure. Yeah. I can hear you. Okay. Yeah. Okay. Yes. All right. I can hear [Music] you. I can hear the two crew set sail for the Red Sea, an area chalk full of wealthy ships seeping out of every orphice like that one. Tommy's first big score was an Indian sloop headed for the Ottoman Empire. The vessel was captured without much effort and was certainly one for the books. Hidden in the hold was millions of dollars worth of gold and silver with millions more worth of spices, ivory, gemstones, spices, silks, and spices. Tommy 2 sailed to a pirate haven on Madagascar to divide the plunder before making his next move. Several months later, two grew a new crew and set sail to wreak havoc once again. It did not end well. While pursuing a 25 ship fleet leaving the Mughal Empire, two engaged one of the lagging ships, said ship turned about to face its attacker and fired a volley of cannons. One of these cannonballs practically split two and two, disembowing the captain and killing him instantly at the age of 44. It is estimated that two's piracy career netted him over $151.9 million in captured goods. There is a lot to say about Sir Francis Drake, but this video is already getting long enough by my standards. So, like an enthusiastic Tinder date, I'm going to trim it up for you. Sir Francis Drake was an English explorer and privateeer and one heck of a sailor starting off as a humble seaman and eventually circumcising the globe. That's not right. Now, that's better. Very early on in his career, Drake grew in incessant hatred and distrust for any and all Spaniards. And now before you think he's racist, it's because the Spanish wouldn't let him break into the West African slave trade. From then on, Drake vowed to attack any Spanish possessions he came across in the future, which he did. He started making good on this promise in 1572 by attacking Panama, a Spanish transfer site of silver and gold from the Pacific Ocean to the Caribbean Sea. Drake and his men raided the area. Despite getting shot in the leg, Drake made off with literal tons of precious metals, making him and his crew rich and famous practically overnight. It was also at this time that Drake became one of the first Englishmen to lay eyes on the Pacific Ocean, letting out an iconic English roar of excitement. Drake vowed that he would one day sail those waters in the future, which he did. Beginning in November of 1577, Drake was granted a fleet of six ships and set sail from Plymouth to trying again in December of 1577. Drake was granted a fleet of six ships and sailed from Plymouth to circle the globe, eventually limping back home in 1580. Along the way, however, Drake made it his mission to be as disruptive to the Spanish as possible. Just one year into the voyage, six ships were whittleled down to just one. Drake's flagship, the Golden Hind. Making it past the southernmost tip of Chile, Drake began bombarding the western coast of South America, ravaging Spanish towns and seizing Spanish ships, one of which was the Newest Seora de la Conpion, which housed over 29 tons of silver bars, silver coins, gold, and jewels. Drake was so tickled pink by this score that he spared the capture ship's crew, even gifting them small amounts of the treasure as they went on their merry way. Fast forward two years and one global circumnavigation later and Drake's back home in England. The queen knights him and everyone briefly claps. He then did some boring political nonsense before hopping back on the saddle and obliterating the ever loving out of some Spaniards. Just like the old days. Speaking of old days, those are the types of days that Drake woke up to in his mid-50s. Still clinging to his youth, the withering and dusty seaman returned to Spanish waters back to where it all started, attacking Panama. Sir Francis Drake died of dysentery in 1596 and was hucked into the ocean in a lead coffin. Across his 33 years of piracy against the Spanish, Drake accumulated upwards of 170.3 million in goods and gold. Last on our list is the one and only Black Sam. No, this one. Despite being known as the single wealthiest pirate in recorded history, his pirating career lasted little more than a year. Black Sam was a real pirates pirate and was renowned for his exceptional generosity and mercy as he boarded your boat and stole all your The so-called prince of pirates began his career as almost all pirates did in the Navy. During his teen years, Sam both metaphorically and quite literally got his feet wet in a few naval battles before branching off to a treasure hunting crew. But when searching for sunken gold didn't pan out, Sam chose to do the next best thing, a life of piracy. He managed to join the crew of one Benjamin Hornold. Remember him? He's the pirate captain that Blackbeard served under in his youth. Well, as a reminder, Hornold refused to attack English ships, much to the dismay of his treasure hungry crew. Hornold and Blackbeard broke away from the majority of the crew to go do their own things, like retire and die, respectively. The remaining crew, however, now turned to Black Sam Bellamy for leadership, and he took the job. About a year later, in 1717, while sailing near Cuba, Bellamy and the boys came across the Wittig Alley, a state-of-the-art English slave ship, practically begging to be captured, which it was. After giving chase for three whole days, Bellamy was finally in range to fire a volley. And after the first shot, the captain of the Widow surrendered. On the ship was a fortune in gold, ivory, and various precious luxuries. Freshly gathered from the sale of over 300 slaves, the Widow was re-engineered into a flagship, being upgraded with more firepower for intimidation purposes, as Bellamy often captured ships with little destruction. It was also common that he would spare his captives, allowing them to flee on the very ships he captured, minus any goods, of course. Can't make a profit on charity. His kind and reasonable demeanor granted him a very loyal crew, and it seemed like Sam had everything going for him. But fate had another idea. Just 2 months after the score of a lifetime, Bellamy sailed from the Spanish Maine to the American Maine. At around midnight on April 26th, 1717, the Winni was caught in a strong noraster storm and was quickly capsized and sank several hundred feet off the coast of Cape Cod. Bellamy and all but two of his 146 crewmen went down with the ship. Guys, in 1984, however, 267 years after its demise, the wreck of the Witta Galley was discovered, including Sam's treasure. Several tons of gold, silver, and gems were recovered from the site, as well as some human remains encased in debris. These are suspected to be Bellamies, though that has yet to be confirmed. Bellamy's exploits earned him a modern-day equivalent of over 177.5 million. That's about 0.045% 045% of Elon Musk's net worth as of me writing this. Guess Sam should have worked harder. Well, that about wraps it up for this video. Why don't you go and watch this one? I'll see you over there. [Music]