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Dan Jones
Before we get started, just a reminder that you now have the opportunity to become a royal favourite subscriber on our new Patreon. It gives you all the benefits of a regular subscription, plus more perks. You can vote on episode topics, chat with fellow history nerds and be in the running to snatch prizes from me, your eminent and benevolent king. Head to patreon.com thisishistory to learn more. The beautiful black warhorse snorts as the knight makes some final checks of his armor. He gathers his reins and pulls down the visor of his helmet. Enclosed in the thick steel, all he can hear is his own breathing. He tries to keep his inhales and exhales slow, bringing down his thudding heartbeat. He holds out his hand for a lance. A squire passes him one and he tucks it tight under his arm. Then he tugs the reins. His horse stamps and turns through his visor slits. The knight once again eyes up his opponent, just over 100 yards away. They've run at each other nine times, driving their lances towards each other's shields, chests and heads, trying to knock each other out of the saddle. So far there's nothing to choose between them. Now there's just one last turn to ride. If the knight is knocked off his horse, it'll be a chastening defeat. If he stays in his saddle, today has been a triumph. But that's easier said than done because his opponent is none other than Boucicault, the greatest warrior in the Western world. This guy has done it all. He went off to war for the first time, aged 12, fought a battle at 16, has led troops on crusade and is so strong and powerful that it's said he can do backflips in full armour and leap from a standing start onto a horse's back with all his kit on. No time to think about reputations though. This is just another man on another horse with another lance under his arm. A flag waves, the crowd roars, both riders kick their horses. The animals break into a canter, then a gallop and in seconds, all the knight can see is the bright shield of the great man, the sharp tip of his lance hammering towards him. He steadies himself. He's done this thousands of times before. He knows everything in this moment depends on him getting the angle of his lance just right, his position in the saddle correct and God smiling on him. The thundering of the hooves gets louder. His heart beats so hard it could burst. 22 year old Henry Bolingbroke holds his breath and braces for the help but feel this is the biggest moment of his young life. It could make or break his reputation. A split second will decide his fate. I'm Dan Jones and from Sony Music Entertainment, this is history. Season 7 of A Dynasty to Die For Episode 7 the Grand Tour.
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Dan Jones
If I asked you to close your eyes right now and conjure up a vision of the Middle Ages, what would you think of? My guess is that for some of you the images would be from a grim period drama. Dirt covered peasants toiling in fields under the lash of a cruel baron, rebels at the gallows having their guts pulled out like sausage links. Villagers writhing in agony as the Black Death strikes. There's some basis in fact for all of that, but perhaps you're seeing another vision of the Middle Ages. The romantic heroic vision. Damsels in exquisite gowns dancing to the latest lute based bangers in amber lit castle halls, Robin Hood types blowing hunting horns in the name of justice beneath the greenwood tree. Or a scene like the one we just heard of brave knights getting together to ride turns against one another in the jousting lists. And you know what? That's rooted somewhere in reality too. In the Middle Ages, there really were knights who sought each other out to test their worth, fighting to a standstill before walking away with their reputations for strength and glory burnished. One such knight is Henry Bolingbroke, cousin, contemporary and sometime rival of the plantagenet King Richard II. When he's in his early 20s, Bolingbroke is building up a personal legend in which he's the absolute paragon of knightly virtue. He isn't doing it in England, where his unwilling entanglement with politics is dragging him towards the first page of Cousin Richard's shit. Listening rather, between 1390 and 1393, Henry is making his name on the road, seeking out the worthiest foes to joust against the most dangerous enemies to fight in the field and the most exotic destinations to visit so that he can claim, with no exaggeration, to be a man of the world. Why he's doing this and indeed who's funding his adventure is what we're going to uncover in this episode because this golden era in young Bolingbroke's life is crucial to understanding who he is and even more importantly, why people are prepared to yield to his charms, which stand in sharp counterpoint to his cousin the Kings. By the way, if you want to learn more about the early history of tournaments under the Plantagenets, we dug into it back in the day in our bonus episodes in season one, which include a deep dive into the origins of the tournament scene under Henry II and Eleanor of Aquitaine. I've put a link to the relevant this is history plus content in today's show. Notes Last episode we heard how in 1388 English politics entered a spiral of vicious, bloody recrimination that was unlike anything seen since the darkest days of Edward ii. Richard had planned to have his own nobles charged with death treason, just for criticizing his government. So at the merciless Parliament, Bolingbroke and four other nobles known as the Appellants, went to town on all the King's favourites, either driving them into exile or lopping off their heads. They then took control of all royal business. While Richard sulked, mourning his best friend and toy boy, Robert de Vere fled England and his beloved tutor Simon Burleigh, who was beheaded in the merciless bloodbath. Since then, things have been orcs, to say the least. The King is gnawing his pillow at night, raging silently against the Appellants and plotting revenge. But the Appellants aren't too happy either. Bolingbroke and Thomas Mowbray, the younger members of the Gang of Five, feel they went too far in killing Burley. The older hands, Thomas of Woodstock and the Earls of Warwick and Arundel are unrepentant. In May 1389, it looks like things are going to get really nasty when, after a year of submission to the appellant's rule, Richard, aged 22, declares he's now officially old enough to do whatever the f he likes. He sacks the Appellant's ministers and starts taking control back into his own hands, inviting them to do something about it, testing their willingness to go through another round of flirting with civil war. Tense isn't the half of it. Then, in the middle of all this chaos, back into England comes the one guy who, in theory at least, can make all all the Boo boos better. It's Bolingbroke's dad, John of Gaunt. He arrives home in November 1389, having spent three years away. In that time, Gaunt fought a series of campaigns in Portugal and Castile, then Gone to whip the English Duchy of Aquitaine in southwest France into shape. Fair play to the old geezer. He's done an amazing job. He hasn't become King of Castile like he said he wanted to, but he's forced a deal on the Spaniards that's provided him with so much gold and silver, it's delivered to him in barrels on a huge wagon train pulled by mules. And Aquitaine is the calmest it's been for a generation. So although when Gaunt was last in England, Richard was talking openly about chopping his head off, now the old guy comes back as a returning hero. Almost right away, politics calms down. Gaunt positions himself as the King's right hand man and he gives the newly formulated Richard is old enough to know best style of kingship a shot of much needed credibility. For most of England's nobles, this is a welcome to release of political pressure. For Bolingbroke, however, it's even more than that. Gaunt's return gets him somewhat off the hook for his part in the merciless Parliament, but it's also an opportunity to spread his wings. If there was ever a time to get the hell out of dodge with no recrimination, now is it? Gaunt can look after the Lancastrian family estates. Gaunt can manage the king. Bolingbroke can go and have some fun. Far away from England, his wife, a young noblewoman called Mary de Boone, is raising their expanding family, three sons and counting on their lands in Peterborough. She's cool with Bolingbroke going off and having a bit of a gap year, so long as he brings back nice gifts now and again. It's all perfectly set up. At 22, Bolingbroke is ready to go and see the big wide world. And ideally, since this is the 1300s, maim some sentient beings along the way. Where to go first, though? Well, that's what he's wondering when an invitation from the great French knight Boucicault lands on his doormat. In the spring of 1390, there's a big tournament happening and it's got Bolingbroke's name on it. Boucicault and his mates are going to stay in the same place, St Angelver, near Calais, for a month. While they're there, they plan to fight literally anyone who wants to come and have a go. Bolingbroke doesn't need inviting twice. So that's how he winds up waggling his lance in the direction of the greatest knight in the world.
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Dan Jones
The cheers that ring in Bolingbroke's ears after he rides his final tilt against Boucico in the tournament at San Anglebert must seem bound to stay with him for as long as there is breath in his body. He knew he was a good sportsman, but now everyone else knows it as well. As he raises his visor and his lance and takes the acclaim of the crowd, it all sinks in. He hasn't just avoided defeat and humiliation, he's absolutely crushed. This, in fact, there's no way anyone is going to do better. When volunteers When Bolingbroke arrived here along with a gang of other young English tyros, he came with a note from his dad, John of Gaunt, asking special permission that Boucicault might ride 10 jousts against Bolingbroke rather than the standard five. That chivalrous request has been granted and Bolingbroke has proven he was worth it. Hop on to this Is History plus this week, if you want to hear me explain why Boucicault is the greatest medieval knight no one talks about enough. And if you're one of our royal favourites on Patreon, stick around after the end of this episode to hear the question I have for you. This week, Bolingbroke has gone toe to toe with this living legend and done better than fine. And this in turn has opened doors to far bigger adventures which will keep him at a safe distance from his cousin Richard II's tempestuous court in England for the foreseeable future. Soon after they've jousted, Boucicault asks Henry for dinner and puts a suggestion to him he can obviously handle himself. How about coming on a bit of a lads adventure to smash the infidel? There's a crusade coming up against some annoying Muslim pirates on the coast of North Africa and Boucicaux can get him involved. Have a think about it. Henry thinks about it for roughly half a second. It's a hard yes. He shoots back to England in May 1390 to rustle up a squad of like minded crusaders and get his dad John of Gaunt's nod of approval and release of funds for this escapade. Both are easy to secure, but then Bolingbroke hit hits a stumbling block. What's not easy is to get the sign off from French King Charles vi. Charles balks at the prospect of Bolingbroke marching with a small army through his territories to Marseille, where the crusade is taking ship. It looks like the whole enterprise is going to fall to bits. Luckily though, there are pagans closer to home who could use a good old fashioned Knights of Albion beatdown. So in the summer of 1390, Bolingbroke heads to Prussia in Northern Europe to join up with the Teutonic Knights. These are a bunch of Templar like hard nuts who love fighting, hate infidels and have a permanent base of operations in Prussia and Lithuania. There, year after year they stick it to the pagans who've lived there since time out of mind. Anyone who fancies a scrap is welcome to do join them. It's not exactly the Holy Land, but it'll do for the next six months. Then Bolingbroke and his mates join the Teutonic Knights on their campaigns, fighting in difficult weather and terrain and making a good fist of it, if you can call a good fist slaughtering human beings and kidnapping their dependents. But let's not get too bogged down in that. Then, in early 1391, Bolingbroke and his chums come back to England, full of the joys of crusading in the Baltic. And almost straight away, they start planning a return visit. Bolingbroke's wife Mary is surprisingly forbearing in putting up with this. Perhaps it's because he also makes sure she has her hands full every time Bolingbroke comes back to England. Mary winds up pregnant by the time he sets out for his second crusade with the Teutonic Knights in summer 1392. They have four sons and a daughter named Blanche. Perhaps it's just our old friend the patriarchy, but if Mary does complain, it never makes it to the historical record. Nor does Bolingbroke's Second Crusade to Prussia. When he arrives back in Teutonic Night country, he finds that a peace deal has been struck with the pagans and there's no fighting to be done. But Bolingbroke is resourceful. Since there's a pause on killing in the Baltic, he's going to switch up the whole mission. How about turning the Crusade into a pilgrimage? It's a stroke of genius, bolingbroke declares. He's going to head a couple of thousand miles southeast of Prussia to Jerusalem. That's a journey that requires immense logistical improvisation and quite a lot of cash. Henry's going to go on a grand tour of the Courts of Bohemia and Hungary, through Venice, to the Greek islands of the Mediterranean, and finally to the Holy Land, following in the footsteps of his very distant relatives, Richard the Lionheart and Edward I. Except actually, Bolingbroke is going to go one better than those famous Kings of Centuries and podcast seasons past as a pilgrim rather than a crusader, he's going to be able to visit Jerusalem and the Church of the Holy Sepulchre itself. After that, he'll head home via Cyprus, Venice again, half a dozen Italian cities, then a stop in Paris before coming back to England. And in the summer of 1393, that's the plan. @ any rate, whether he makes it on this crazy adventure is another matter altogether. But what's certain is that in the early 1390s, freed from the parochial pettiness of Richard's court, Bolingbroke has done some proper growing up. And why not? Fate granted him the opportunity to have some some fun, and he'd have been the greatest fool ever born if he didn't grab it with both hands.
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Dan Jones
Mary Deboon looks up from studying the book on the table before her as she hears a strange noise. It's a hissing noise, and she can't think For a moment, what it might be, it comes again and again. Then it's joined by another sound, equally as bizarre. It's a sort of high pitched chirrup, which comes again and again. Worried, Mary closes the book, stands up and goes to the window. Her first instinct is to wonder where her children are. The four boys, Henry, Thomas, John and Humphrey, have been off playing or taking their lessons. Baby Blanche must be with her nurse. Deep maternal instinct tells Mary she needs to fear for them. When she looks out of the window, she sees she was right and wrong. Looking into the sharp July sunlight, she can see what's making the peculiar noises. It's a whole menagerie of wild animals. The hissing is coming from a huge bird with a long neck, scrawny legs, a fat body and one of the ugliest faces she can begin to imagine on the front of a stupid little head. The chirruping, meanwhile, is coming from a massive, fierce cat, roughly as big as a lion, but covered all over in spots. Incredibly, this cat is riding on the back of a horse, sitting on a thick blanket so its claws don't tear the obviously well trained horse's flesh. Mary is an avid reader, and she's seen enough bestiaries in her time to hazard a guess at what these exotic beasts are. An ostrich and a cheetah, and there's plenty more besides. They're part of a great train of riders and carts coming along the drive to the house. At the front of this procession, this exotic caravan of wonders brought to England from the ends of the earth, is a man she hasn't seen for far too long. It's her charming, wandering husband. Henry Bolingbroke is back. Among the many gifts Bolingbroke returns bearing is a commitment not to go gadding about again for a while. His adventure has cost nearly 5,000 pounds. While that doesn't really dent the family fortunes of the Lancastrians, thanks to Gaunt's Castilian windfall, it's still quite a chunk of choice change. It's July 1393, when Bolingbroke returns from his long journey to Jerusalem. As tradition has it, Mary's up the duff again pretty much immediately. By the early summer of the following year, she's given birth to a second little girl who's named Philippa. That means Bolingbroke and Mary have six children in total, all of them healthy youngsters. They're lavished with good educations, and the expenses from their household suggest a cheerful environment with books and music and fine clothes and delightful things brought up to Peterborough from the best shops in London. And of course, they now have a pet ostrich and cheetah, more of which we'll get onto in today's bonus episode of this is history plus. But this isn't just a domestic idyll in Richard II's England. It really matters, because the expansion of Henry Bolingbroke's family stands in sharp contrast to the absolute non expansion of Richard's. The King has been married to Anne of Bohemia for a decade and there's been no evidence of the slightest twitch of sexual activity between them. Richard is childless and heirless, and it may well be that that's the way he likes it. This is a king, after all, who sees anyone who detracts from his own majesty as a threat. He pretty much refuses to discuss the succession at all. It's hard to see him standing by proudly as relatives go coochie coochie coo under a baby's chin, he's more likely to feel incensed that no one's giving him a good dandel. So as Henry Bolingbroke's family grows and Richards doesn't, the implied threat of the King's cousin just starts to nudge up a little. Could John of Gaunt's line be a dynasty in waiting? That's for next time on this Is History. Hello, Dan here again. Remember, over on our Patreon, you can keep the chat going about this episode as a royal favourite. And this time, we want to hear from the intrepid travellers. If you caught the travel bug in the 1390s, where would you like to go? Head to patreon.com thisishistory to give us your medieval travel bucket list and I shall also share mine.
This is History: A Dynasty to Die For – Season 7, Episode 7: "The Grand Tour"
Hosted by Dan Jones | Production by Sony Music Entertainment | Release Date: June 10, 2025
The episode opens with a vivid portrayal of a medieval joust, setting the stage for the intense rivalry between two formidable knights. Dan Jones immerses listeners in the high-stakes environment of a knightly tournament, highlighting the physical and psychological demands placed on the competitors.
"The thundering of the hooves gets louder. His heart beats so hard it could burst." (00:00)
This dramatic introduction serves as a metaphor for the impending conflict between Henry Bolingbroke and Richard II’s court, emphasizing the turbulent nature of the Plantagenet dynasty.
Dan Jones delves into the character of Henry Bolingbroke, painting him as the epitome of knightly virtue and ambition. In his early twenties, Bolingbroke is not content with the political intrigues of England but seeks to build his legend through valorous deeds across Europe.
"At 22, Bolingbroke is ready to go and see the big wide world. And ideally, since this is the 1300s, maim some sentient beings along the way." (04:38)
Jones explores Bolingbroke's motivations, suggesting that his adventures are both a means to personal glory and a way to distance himself from the fraught political landscape dominated by his cousin, King Richard II.
A pivotal moment in Bolingbroke's quest for renown is his extraordinary joust against Boucicault, hailed as the greatest warrior of the Western world. This matchup is portrayed as a defining moment for Bolingbroke, cementing his reputation as a formidable knight.
"He hasn't just avoided defeat and humiliation, he's absolutely crushed. This, in fact, there's no way anyone is going to do better." (14:26)
Jones emphasizes the strategic and physical prowess required for such a victory, highlighting Bolingbroke's skill and determination. This triumph not only elevates Bolingbroke's status but also sets the stage for his subsequent adventures.
Following his victory, Bolingbroke is invited by Boucicault to join a crusade against Muslim pirates in North Africa. Although initial plans to march through French territories encounter political obstacles, Bolingbroke adapts by joining the Teutonic Knights in Prussia.
"In the summer of 1390, Bolingbroke heads to Prussia in Northern Europe to join up with the Teutonic Knights... Anyone who fancies a scrap can join them." (12:53)
Jones details Bolingbroke's involvement in the Baltic Crusades, highlighting his relentless pursuit of martial excellence and his ability to navigate the complex political and military landscapes of medieval Europe.
Amidst his military exploits, Bolingbroke returns to England to tend to his growing family. His wife, Mary de Boone, manages their household and children with grace, allowing Bolingbroke the freedom to embark on further adventures.
"Mary winds up pregnant by the time he sets out for his second crusade with the Teutonic Knights in summer 1392. They have four sons and a daughter named Blanche." (21:49)
Jones portrays the domestic side of Bolingbroke's life, juxtaposing his noble pursuits with his responsibilities as a husband and father. This balance adds depth to Bolingbroke's character, illustrating the personal sacrifices made in the pursuit of glory.
As Bolingbroke expands his family and builds his legacy, King Richard II remains stagnant, childless, and increasingly isolated. This stark contrast underscores the brewing tension between the two, hinting at the potential for future conflict.
"As Henry Bolingbroke's family grows and Richard's doesn't, the implied threat of the King's cousin just starts to nudge up a little." (21:49)
Jones suggests that Bolingbroke's burgeoning dynasty poses a significant challenge to Richard II's reign, setting the stage for the eventual power struggle that threatens to destabilize the Plantagenet rule.
The episode underscores how Bolingbroke's actions—his military victories, familial expansion, and growing influence—lay the groundwork for a dynastic shift. His leadership qualities and charisma contrast sharply with Richard II's authoritarianism, making Bolingbroke a rallying figure for those dissatisfied with the king's rule.
"If John of Gaunt's line could be a dynasty in waiting? That's for next time on this Is History." (21:49)
Jones hints at the impending rise of Bolingbroke, foreshadowing the eventual overthrow of Richard II and the establishment of the Lancastrian dynasty.
Dan Jones wraps up the episode by highlighting Bolingbroke's growth from a young knight seeking glory to a pivotal figure poised to challenge the existing power structure. The expansion of his family and influence not only personalizes the historical narrative but also illustrates the broader dynastic tensions of the period.
"Henry Bolingbroke has done some proper growing up. And why not? Fate granted him the opportunity to have some fun, and he'd have been the greatest fool ever born if he didn't grab it with both hands." (14:26)
Jones leaves listeners anticipating the next episode, where the simmering tensions between Bolingbroke and Richard II will likely culminate in dramatic historical events.
"The thundering of the hooves gets louder. His heart beats so hard it could burst." – Dan Jones at 00:00
"At 22, Bolingbroke is ready to go and see the big wide world. And ideally, since this is the 1300s, maim some sentient beings along the way." – Dan Jones at 04:38
"He hasn't just avoided defeat and humiliation, he's absolutely crushed. This, in fact, there's no way anyone is going to do better." – Dan Jones at 14:26
"As Henry Bolingbroke's family grows and Richard's doesn't, the implied threat of the King's cousin just starts to nudge up a little." – Dan Jones at 21:49
"Henry Bolingbroke has done some proper growing up. And why not? Fate granted him the opportunity to have some fun, and he'd have been the greatest fool ever born if he didn't grab it with both hands." – Dan Jones at 14:26
Stay tuned for the next episode, where the brewing conflict between Henry Bolingbroke and King Richard II threatens to reshape the Plantagenet dynasty.