Skip to content
Home » Articles » The Adventures of Young Henry of Bolingbroke

The Adventures of Young Henry of Bolingbroke

Photo of re-enactor playing a knight

In the late 1398, Henry Bolingbroke fell out of favour with King Richard II and was exiled.  Within a year he returned and seized the throne to become King Henry IV.  

The story of Richard’s fall and Henry’s reign is well known thanks mainly to Shakespeare.  However, Henry’s life prior to the cataclysmic events of the late 1390s is a less familiar story. 

Young Bolingbroke was famed for his jousting prowess and valorous deeds on the field of battle.  However, he was far more than just a warrior.  He was also well-travelled, well-read, multilingual, and a talented musician.

This, then, is the story of the adventures of the young Henry Bolingbroke.  The story of the making of a self-made king. 

The Child

Henry was born on 15th April 1367 at Bolingbroke Castle in Lincolnshire.  He was the son of John of Gaunt, the wealthy Duke of Lancaster.  His father was one of the most powerful men in England.  His grandfather, Edward III, reigned as king of England. 

Bolingbroke was pretty much the same age as his cousin, Richard II.  For this reason, many people thought of them as a pair (they were the only two royal cousins of such a similar age at the time).  However, as it would turn out, they could not have been more different. 

The young Richard was raised primarily in France.  Henry, by contrast, grew up in England, mainly on the Lancastrian estates.  The two would not even meet until they were five or six.  At this time Richard spoke very little English, whereas Henry spoke it fluently.  It was just the first of many differences that would mark them out as very different men in later life.

The Student

From 1374, Bolingbroke was placed under the governorship of Thomas Burton, an old servant of Henry’s maternal grandfather, Henry of Grosmont.   Grosmont was the first Duke of Lancaster, a title he’d earnt whilst fighting in France in the 1340s with Edward III.  The old Duke Henry had a considerable reputation as a warrior, having served as the king’s lieutenant no fewer than seven times.  Burton no doubt did his best to instil the same martial values in young Bolingbroke.

Burton also arranged for Henry to be tutored by his chaplain, Hugh Herle.  The boy proved a keen student, learning to write fluently in English, French and Latin.  Whilst other English noblemen of the time often delegated the task of writing to others, Henry, somewhat unusually, preferred to write in his own hand.

The Husband

Henry married Mary Bohun in February 1381.  It was a successful marriage and the two shared much in common.  Both were keen musicians and lovers of books.  Indeed, Mary’s family was one of the foremost book publishers in England at the time.  The couple rapidly acquired an extensive library.

Henry and Mary would have six children together, including the future King Henry V.   However, at the time of their wedding, Mary was only 11 and Henry about two years older.  Too young to be starting a family.  Nevertheless, that year, on turning 14, Henry came of age in medieval eyes.

The Survivor

That summer the Peasants’ Revolt erupted across southeast England.  Bolingbroke was forced to take refuge in the Tower of London along with Archbishop Sudbury and several other government officers. 

The small garrison proved entirely inadequate to prevent the mass of angry peasants from breaking in.  The mob seized Sudbury, one of the most hated men in the Ricardian regime, dragged him outside and summarily executed him.  It is said it took as many as eight blows to behead the hapless Archbishop.  Prior Hales, another prominent member of the regime, quickly met the same fate.

The mob proceeded to kill five more, including William Appleton, targeted for no other reason than being John of Gaunt’s physician.  The mob now turned their attention to Henry.  Henry’s father was the man they blamed most for the hated poll tax.  He now stood in great danger.

At this point one of the guards, John Ferrour, stepped between the mob and Bolingbroke and pleaded for the boy’s life.  Ferrour must have been a convincing orator because he somehow managed to persuade the crowd to spare the young man.  A narrow escape! 

The Knight

In January 1382, still only 14, Bolingbroke took part in a jousting tournament at Smithfield.  He wore an impressive suit of armour, adorned with silver spangles, fashioned in the image of roses.  Bolingbroke quickly established a reputation as a skilled jouster, appearing again on the tournament lists at Hereford on May Day that year.

Photo of re-enactor on a horse in a joust
Jousting in the late C14th was a key way in which a nobleman could build a reputation for valour and chivalry

A few years later, in March 1389, at St Inglevert, three renowned French knights challenged all comers to what was known as a ‘joust of war’.  This was the most dangerous form of the sport, in which knights used uncapped lances.  Serious injury and even death was a very real risk.  Among the three was Sir Jean le Maingre, better known as ‘Boucicaut’, one of the most formidable jousters in Europe.

The French knights agreed to joust five strokes with anyone who challenged them.  Bolingbroke traded not five strokes but ten with Boucicaut.  It was a most honourable draw.  At the end of the tournament, Boucicaut judged Henry to be one of the most admirable of all his challengers.

The Appellant

By 1387 there was widespread dissatisfaction with the Richardian regime.  Richard had failed to deliver any great military successes and had surrounded himself with a group of unpopular favourites.  Elder statesmen of the time such as Thomas of Woodstock (Henry and Richard’s uncle) and the Earl of Arundel, regarded the young king as irresponsible and immature.

Woodstock, Arundel and the Earl of Warwick, invoked an ancient chivalric legal challenge known as the Appeal.  For this reason, they became known as the Lords Appellant.  They used the Appeal to accuse Richard’s favourites of corrupt and evil councils and demand their removal from office. 

The three original Appellants were later joined by Thomas de Mowbray, the Earl of Nottingham and Henry Bolingbroke. 

The General

Richard responded by sending Robert de Vere to Cheshire to raise a royal army and crush the Appellants.  But, as de Vere marched south, he found himself outmanoeuvred.  An army led by Bolingbroke blocked his advance at Radcot Bridge and, in the ensuing battle, the royalist army was routed. 

Richard was now at the mercy of the Appellants.  The Appellants considered deposing Richard, but Henry and his uncle could not agree on who should replace him.  In the end it was decided that Richard’s powers should be suspended and replaced by rule by council.  Richard remained king in name only.  It was a coup d’état. 

In the reckoning that followed, a hot-tempered Woodstock pressed for the execution of a great many of Richard’s favourites.  But when he demanded the execution of Sir Simon de Burley, the king’s former tutor, it was a step too far for Henry.  Burley had been Henry’s tutor too and Henry joined Richard in pleading for his life.  It was to no avail; the senior Appellants had their way and Burley was executed.

Bolingbroke’s victory at Radcot Bridge confirmed his military prowess but permanently damaged his relationship with Richard. 

The Musician

By his early twenties, Bolingbroke had an impressive reputation as a knight, a military commander, and statesman.  He was seen as a man much more in the mould of Edward III than his cousin the king. 

However, there was a lot more to Henry than just the warrior. 

One of Henry’s main interests, when he had time to himself, was music.  He liked to have minstrels play for him at every meal and both he and his wife Mary were keen musicians.  They arranged choirs, sang, and played cithers and harps together.

In 1395 he even paid to have a cithara brought from Leicester to Kenilworth for him, so that he could play.   He encouraged a love of music in his children, buying the future Henry V a harp and arranging for him to have lessons.

Henry may also have composed music.  Two pieces of polyphony are ascribed to a ‘King Henry’ in one of the earliest collections of English sacred music.

Photo of a 16th century cither
Henry and his wife both played the cither

The Philosopher

Bolingbroke was also an academic and an intellectual.  Unusually for his time, he was fluent in written English, Latin and French.  He could also write in Greek, although not enough of his written Greek survives to judge his fluency.

He maintained a significant library containing a wide range of books on subjects including histories, religious works, poetry, and philosophy (but nothing light-hearted or frivolous).

The writer, historian and scholastic philosopher, John Capgrave, later wrote of Henry:

“…he was a man of very great ability, and of so tenacious a memory that he used to spend a great part of the day in solving and unravelling hard questions…he was a studious investigator of all doubtful points of morals…he was always eager to pursue such matters.”

John Capgrave

In keeping with Henry’s passion for all things logical, he owned an early clock.  Henry appears to have relied on it to organise his day, even to the extent of taking it with him whilst travelling overseas.  How ‘portable’ this device truly was is unknown.  However, technically, it stands as the earliest recorded portable clock in history!

The Crusader

After the tumultuous events of 1388, Richard II did not trust Bolingbroke with any significant office of state.  Henry, now in his prime, found he had relatively little of consequence to occupy his time.  Jousting, music, and reading were not enough.  So, in 1390, he decided to set off on a crusade.

Henry travelled with a small retinue east, across the Baltic Sea to Lithuania.  There he and his party joined up with the Teutonic knights.  The knights had been waging a campaign against the pagans of Lithuania for several decades.  However, by the time Henry arrived in 1390, many Lithuanians had already converted to Christianity.  The fighting now had a lot more to do with local power politics than religion.

Photo of a re-enactor on a horse dressed as a 14th century crusader
The Teutonic knights carved out their own state in east Prussia and the Balkans during the C14th

A struggle was in progress between Grand Duke Jagiello and his cousin Vytautas for the Lithuanian Dukedom.  Both were Christians and, although many pagans supported Jagiello, the conflict was mainly a political one.  The Teutonic Order sided with Vytautas and it would be for this faction which Henry would fight. 

The Hero

On 22nd August, Henry’s party rendezvoused with Marshal Rabe of the Teutonic Order at Insterberg Castle.  They marched north with Vytautas’ Lithuanians and met an enemy force of Lithuanians and Russians commanded by Jagiello’s brother Skirgiello.

In the ensuing battle, Henry’s retinue played a key role.  His archers disrupted the enemy defences, shielding the main advance.  The combination of English archers and German knights proved deadly.  Skirgiello was defeated and several Russian and Lithuanian nobles were taken prisoner.

The victorious crusaders pressed on to besiege Vilnius.  In the ensuing conflict Henry again distinguished himself.  He led the first assault, fighting his way through to plant the flag of Saint George above the town parapet.

Although the town’s outer defences were breached, the castle protecting it never fell.  The siege dragged on and eventually Henry had to return home, finally arriving back on English soil in April 1391.  He even returned with two captured Lithuanian children, whom he had converted to Christianity.

His adventures in Lithuania won Henry great renown.  Serving on crusade was considered a great honour and Henry was the first English prince of the blood to do so since Edward I. 

The Traveller

In the summer of 1392 Henry returned to eastern Europe, hoping to join the Teutonic Order on crusade again.  However, disaster struck – peace broke out.  With no war to fight, there would be no crusading and with no crusading, there was no glory to be had.  What could Henry do?  To have travelled so far across Europe for no reason entailed a loss of face.

Henry took a while to consider his options and then decided he would set out on a pilgrimage – to the Holy Sepulchre in Jerusalem no less.

Henry’s pilgrimage would take him until January of the following year to complete.  Over the course of this long journey, he would visit the court of King Wenceslas in Prague where he was entertained as an honoured guest.  A number of knights present at court had seen Henry joust at St Inglevert in 1389 and sang his praises to the king.

Departing from Prague, Henry next visited the King of Hungary and then Vienna before making his way to Venice where he was entertained by the Doge.  Being an English royal with such a reputation as a knight and crusader, ensured Henry was treated as a celebrity.

The Pilgrim

At last Henry finally set out on the sea voyage from Venice to the Holy Land, making his way to Jerusalem.  He was the first English royal to set foot in the Holy Land since Edward I and the first ever to visit the Holy Sepulchre itself.

Photo of the Holy Sepulchre in Jerusalem today
The Holy Sepulchre in Jerusalem

Henry was now every inch a perfect knight.  A famous jouster, experienced soldier, renowned crusader and now a pious pilgrim who’d paid homage at the sacred sepulchre of Christ himself.  It is small wonder that, on his return journey, the Duke of Milan’s cousin, Lucia Visconti, appears to have been smitten by him.  When, seven years later, she was asked whom she desired to marry she replied that if she could be sure of marrying Henry, she would gladly wait for him forever.

By the time Henry returned to London in the summer of 1393, his reputation could not have been higher.

The Outsider

Henry’s return to England would bring with it disappointment.  In 1394 his cousin the king continually overlooked him when it came to assigning important offices of state. 

1394 would also bring him tragedy when his beloved wife Mary died in childbirth.  At 27, Henry was a widower.  For some time afterwards he appears to have avoided the places where he’d spent the most time with Mary.  The memories, it seemed, were too painful.  He would not re-marry until nearly a decade later, after becoming king.

Later that year, John of Gaunt set sail for Gascony to shore up his position as Duke of Aquitaine.  And when Richard II set off to campaign in Ireland he appointed his uncle, Edmund of York, as his keeper of seals.  This empowered Edmund to act as regent in Richard’s absence. 

It was a public snub to Henry as the position was usually reserved for the heir presumptive to the throne of England.  By appointing Edmund rather than Henry, Richard was signalling that the house of Lancaster was not as favoured in the line of succession as York.

The Patron

Henry was nevertheless appointed by his uncle to be the receiver of petitions for the parliament of January 1395.  With the king away in Ireland, the main business of parliament was granting the king additional finances for his Irish campaign.  However, parliament also had to decide what to do about the famous ‘twelve conclusions’ of the Lollards that had been discovered nailed to the door of Westminster Abbey.

To most of the lords present, the ‘twelve conclusions’ represented shocking heresy.  Henry, ever the religious traditionalist, was among the first to condemn it. His name appears at the top of the signatories to a letter asking the king to return to England to deal with the heretics.  However, Richard was too busy in Ireland and would not return to England until May.

1395 was an otherwise uneventful year for Henry.  Having little else to do, Henry read, jousted, and listened to music.  At this time, he added the poet, Geoffrey Chaucer, to his household.  Chaucer remained with him for the rest of the year and, at Christmas, was rewarded for his service with £10 and a gift of a furred robe.

The Duke

Henry certainly visited Richard at court during the mid-1390s and their relationship remained courteous but hardly close.  Henry just wasn’t part of Richard’s inner circle as evidenced by the fact that he was consistently overlooked for any prestigious offices.

Richard II’s campaign in Ireland had been a success.  It had greatly enhanced his reputation and played a key role in re-building his authority during the 1390s.  By 1397 Richard felt secure enough to finally take his revenge on the Appellants.

When the axe finally fell, the primary targets of Richard’s wrath were the three senior Appellants, especially Woodstock and Arundel.  Within a few weeks Woodstock and Arundel were dead.  Richard’s purge of his enemies was every bit as brutal as the Appellants’ coup of a decade before.

Richard may have snubbed Henry for his role at Radcot Bridge, but Henry’s attempts at mediation at the time saved him.  Indeed, in the initial aftermath of Woodstock’s downfall, Richard even chose to reward Henry by granting him the title of Duke of Hereford.

The Gathering Storm

After the summer of 1397, Richard’s reign increasingly descended into tyranny.  Henry may have survived the initial purge, but uncertain times lay ahead.  All the while Richard became increasingly paranoid, apt to see potential traitors wherever he looked.

Storm clouds were gathering. 

Then, in December 1397, Henry had a fateful encounter with fellow former Appellant Thomas de Mowbray on the road to London.

“We are to be undone,” warned de Mowbray, “…because of what was done at Radcot Bridge.”  

These ominous words placed Henry on a collision course for confrontation with Richard.

Henry was 30 years old; his days of youthful adventure were well and truly behind him.  From now on his life would be consumed by the serious and dangerous game of power politics.

Keep up to date with our stories

If you like reading our work and would like to keep up to date with the latest stories and news from our blog page, you can follow us on Facebook.  We always announce any news and promote new stories as they are published here:

References & further reading:

The Fears of Henry IV: The Life of England’s Self-Made King, Ian Mortimer, Vintage, 2008 

Richard II and the Revolution of 1399, Michael Bennett, Sutton Publishing, 1999

The Plantagenets: The Kings Who Made England, Dan Jones, William Collins, 2013

If you would like to read more about the reign of Richard II, I have written a series of articles covering a detailed history of his reign and its impact.  Here are the links:

Read Part 1 – Richard II, the boy king here – this article covers the early part of Richard II’s reign, his role in the peasants’ revolt and his confrontation with the Lords Appellant.

Read Part 2 – The tyranny of Richard II here – this article covers the later part of Richard’s reign and the final chaotic years that led to his downfall.

These articles form part of a related series of pieces I am writing, tracing the history of the fall of the Plantagenet dynasty, culminating in the Wars of the Roses.  The first article in this series provides an overview of the period and takes an in-depth look at the final years of Edward III.

Read my first article on The Wars of the Roses and the fall of the Plantagenets here.


Portrait photo image of a knight in profile in Henry IV(ish)  livery – cropped from the Knights’ Tournament in Łęczyca (2014), Darekm135 (from Wiki Commons)

Jousting – photo taken at Middelaldercentret by Toxopolis (from Wiki Commons)

A photo of a Cither (C16th version of the instrument) by S Guastevi (from Wiki Commons)

Picture of a Teutonic knight taken at Knights’ Tournament in Łęczyca (2014) by Darekm135 (from Wiki Commons)

Photo of the Church of the Holy Sepulchre by Gerd Eichmann (from Wiki Commons)

Leave a Reply

Your email address will not be published. Required fields are marked *