In the high summer of 1399, King Richard II of England stood at what seemed the apex of his authority. Having ruthlessly purged his political enemies, the Lords Appellant, two years prior, he now reigned with an aura of divinely-ordained majesty, his personal emblem of the White Hart a ubiquitous symbol of his power. To secure his western dominion, he had sailed to Ireland with a formidable army, confident that his kingdom, governed by his loyal uncle Edmund, Duke of York, was secure. Yet, in less than three months, his throne would be lost, his authority shattered, and he would be a prisoner awaiting a lonely death. The astonishingly rapid collapse of Richard’s regime was not merely a military defeat; it was a profound political statement, a sign that for a critical mass of the English nobility and gentry, the king’s grace had failed, and legitimacy no longer resided with the anointed monarch. The catalyst for this revolution was the return from exile of one man: Henry Bolingbroke, Duke of Hereford and Lancaster.
The Tyranny of the 1390s: A Kingdom on Edge
To comprehend the events of 1399, one must first understand the preceding decade. The ‘tyranny’ of Richard II, as his enemies would later brand it, was a complex blend of autocratic policy, financial extortion, and a deeply personal style of kingship that alienated the very men whose support was essential for governance.
Following the Merciless Parliament of 1388, which had humiliated him and executed his friends, Richard had spent years rebuilding his power. By 1397, he was ready for revenge. He arrested three of the senior Lords Appellant: his uncle Thomas of Woodstock, Duke of Gloucester; Richard Fitzalan, Earl of Arundel; and Thomas de Beauchamp, Earl of Warwick. Arundel was tried and executed in a tense and vindictive parliamentary session. Warwick was condemned and exiled. Gloucester, the most powerful of the three, was spirited away to Calais and there murdered, almost certainly on the king’s command. The message was clear: opposition to the king’s will was treason, punishable by death.
This political purge was accompanied by a fiscal offensive that struck at the heart of the landed class. Richard’s government began demanding forced loans and levying punitive fines, known in popular memory as ‘blank charters’—signed and sealed documents that the king’s agents could later fill in with any sum they chose. For the knights and landowners of shires like Lincolnshire, this was a terrifying and deeply unconstitutional development. English kings were expected to ‘live of their own’, funding government from their own estates and customary revenues. War or extraordinary circumstances might justify taxation granted by Parliament, but this arbitrary extortion felt like a violation of the fundamental rights of property. A landowner in the wapentake of Lawress, near the Barony of Brattleby, might find his entire livelihood threatened not by a foreign enemy, but by his own king.
The final and most catastrophic act of Richard's reign was his decision regarding the Lancastrian inheritance. In February 1399, Henry Bolingbroke’s father, the immensely wealthy and respected John of Gaunt, Duke of Lancaster, died. Gaunt, despite his power, had often acted as a moderating influence on the king. With him gone, Richard saw his chance. He cancelled the legal documents that would have allowed the exiled Bolingbroke to claim his inheritance from abroad and, in an act of breathtaking arrogance, extended Henry’s ten-year exile to a life sentence and confiscated the entire Duchy of Lancaster for the Crown.
This was Richard’s fatal error. The Duchy of Lancaster was not merely a collection of estates; it was a palatinate, a kingdom within a kingdom, with its own administration and vast revenues. By seizing it, Richard did more than disinherit one man. He attacked the principle of hereditary succession itself. If the king could arbitrarily seize the greatest private inheritance in the realm, what was to stop him from doing the same to any lesser baron or knight? Every landowner in England, from the mightiest earl to the smallest freeholder, now had cause to fear for his own property and his children’s future. The king, who was meant to be the ultimate guarantor of law and property, had become its greatest threat.
The Return: A Lone Ship at Ravenspur
On or around 4 July 1399, a small vessel made landfall at Ravenspur, a now-lost port on the shifting coast of the Humber estuary. Aboard were Henry Bolingbroke and a handful of followers, including the exiled Thomas Arundel, former Archbishop of Canterbury. It was no invasion force. Henry’s genius lay in his initial political positioning. He did not arrive with banners flying, claiming the throne. Instead, he sent word that he had returned with a singular, lawful purpose: to reclaim his rightful inheritance as Duke of Lancaster, a right a just king would not deny.
This moderate claim was a masterful piece of propaganda. It allowed men of conscience to support him without immediately committing treason. Word spread like wildfire across the north. Henry began to march south, and his small band of companions began to swell into an army.
The key to his success lay in the immediate defection of the most powerful magnates in the north: the Percys. Henry Percy, 1st Earl of Northumberland, and his famously martial son, Sir Henry ‘Hotspur’ Percy, met Bolingbroke and pledged their swords to his cause. The Percys’ motives were complex. They had grievances with Richard over Scottish border policy, but more fundamentally, they saw the political winds changing. As great landowners themselves, with significant holdings across Yorkshire and into Lincolnshire, they understood the threat posed by Richard’s seizure of the Lancastrian estates. By backing Henry’s claim to his duchy, they were defending the rights of their entire class. Their support was the crucial domino. With the Percys came their vast network of retainers, knights, and men-at-arms.
The Lincolnshire Connection: A Shire Chooses its Master
News of Henry’s landing would have travelled with astonishing speed down the Roman roads of Lincolnshire. Riders would have galloped south along Ermine Street, past Lincoln’s imposing cathedral and castle, carrying the news that would force every significant family in the county to make a perilous choice. To support Henry was to risk the wrath of a vengeful king should he return victorious from Ireland. To support Richard was to side with a monarch who had lost the trust of his people and whose local agents were deeply unpopular.
For the Barony of Brattleby, this was no distant political drama. By the late 14th century, the manor of Brattleby was held as part of the Honour of Richmond by the powerful Nevill family of Raby. The head of the house, Ralph Nevill, 1st Earl of Westmorland, was married to Joan Beaufort, Henry Bolingbroke’s half-sister. His allegiance was never in doubt. Westmorland was one of the core group of northern lords, alongside Northumberland, who immediately joined Henry. His decision meant that the revenues, influence, and men of his estates—including those tied to Brattleby—were now placed at Bolingbroke’s disposal. The local men of Brattleby, Aisthorpe, and Cammeringham, tenants of the Nevills, would have found themselves, by feudal obligation and loyalty, part of the growing Lancastrian host.
Another of Lincolnshire’s greatest magnates, William, 4th Lord Willoughby de Eresby, also made his choice. A veteran of Richard’s earlier campaigns, Lord Willoughby’s vast estates dominated the Fens and south Lincolnshire. He was one of the first and most important nobles to join Henry as he marched south, meeting him at Doncaster. His support provided Henry with further legitimacy and, crucially, more soldiers. Other prominent Lincolnshire families, like the Tailboys and the Dymokes of Scrivelsby—the family of the hereditary King's Champion—also threw in their lot with the returning duke. The rapid alignment of the Lincolnshire gentry behind Bolingbroke was a microcosm of what was happening across England. It was not a reluctant, fearful submission to a conqueror; it was an active and willing transfer of allegiance. Richard’s authority in the shire had evaporated overnight.
The Regent's Paralysis and the King's Capture
While Henry’s support snowballed, the government in London was paralysed. The Regent, Edmund, Duke of York, was a man trapped by circumstance. He was Richard’s uncle, but also John of Gaunt’s brother and thus Henry’s uncle, too. He was temperamentally unsuited for a crisis, and fundamentally disagreed with Richard’s seizure of Henry’s inheritance. York tried to raise an army at St Albans, but found little enthusiasm. The funds were low, and the magnates he summoned were either prevaricating or already riding to join Henry.
Worse, key members of Richard’s own household betrayed him. William Scrope, Earl of Wiltshire and the king’s Treasurer, fled with other loyalists, taking refuge in Bristol Castle. York, seeing his position as untenable, marched his small, unreliable force west, not to confront Henry, but to await the king’s return from Ireland. In a pivotal moment, he met Henry’s army near Berkeley Castle in Gloucestershire. After a tense conference, York abandoned the king's cause and submitted to his nephew. The royal government had officially collapsed. Henry, now in command of the only significant military force in the country, marched on Bristol, captured Scrope and other Ricardian loyalists, and had them executed after a summary trial. This was a clear escalation: Henry was no longer just a petitioner; he was dispensing justice as if he were the ruler of the realm.
Meanwhile, Richard II finally landed at Milford Haven in Wales around 25 July, completely unaware of the scale of the disaster. He expected to find armies waiting for him. Instead, he found only fear and desertion. His forces, hearing of the defections and Henry's unstoppable advance, melted away into the Welsh hills. Richard, with a dwindling band of followers, retreated to the safety of the great North Welsh castles—Flint and Conway.
It was at Conway Castle that the final act of his reign played out. Henry sent the Earl of Northumberland to negotiate. According to chronicles, including the detailed account by the French knight Jean Creton, who was with Richard, Northumberland came to the king and swore a sacred oath on the consecrated Host that if Richard would agree to a parliament to restore Henry’s lands and return with him to London, he would not be harmed. Richard, desperate and with no other option, agreed. It was a trap. On the road from Conway, Richard’s party was ambushed by a large force of soldiers hidden by Northumberland. His last vestige of freedom was gone. He was now Henry Bolingbroke’s prisoner. The ride back to London was a calculated pageant of humiliation, as the once-resplendent king was paraded before his former subjects, who now greeted him with jeers and insults.
The Usurpation: Parliament and the Empty Throne
Henry Bolingbroke now faced a conundrum. He had the king, and he had the kingdom, but he did not have the crown. Simply deposing an anointed king was a revolutionary act, fraught with legal and spiritual danger. Henry and his advisors, therefore, orchestrated a careful constitutional process to give the usurpation the veneer of legality.
First, on 29 September 1399, a delegation of lords visited the captured king in the Tower of London. There, under immense duress, Richard was "persuaded" to sign a deed of abdication, renouncing his throne with a seemingly cheerful countenance, as the official record, the Record and Process, would later claim.
The following day, Parliament assembled in Westminster Hall. It was the same assembly Richard had summoned before leaving for Ireland, but its purpose was now entirely different. The throne stood empty. The Speaker read out Richard’s supposed voluntary abdication. But this was not considered sufficient. To justify the deposition and ensure Richard could never again claim the throne, a list of thirty-three articles of accusation was read out to the assembly. They catalogued his crimes: the murder of the Duke of Gloucester, the execution of the Earl of Arundel, the raising of illegal taxes, the confiscation of the Lancastrian inheritance, his declaration that the laws were “in his own mouth and breast,” and his general autocratic behaviour. The assembled lords and commons unanimously accepted the charges and formally deposed King Richard II.
The throne was now officially vacant. At this dramatic moment, Henry Bolingbroke rose from his seat. Instead of claiming it by right of conquest, which would have implied the kingdom was his personal property, he made a carefully worded, ambiguous claim in English (not the customary French), appealing to multiple sources of legitimacy:
"In the name of the Father, Son and Holy Ghost, I, Henry of Lancaster, challenge this realm of England, and the crown with all its members and appurtenances, as I am descended by right line of blood coming from the good lord King Henry III, and through that right that God of his grace has sent me, with the help of my kin and of my friends, to recover it; the which realm was in point to be undone for default of governance and undoing of the good laws."
His genealogical claim was weak (the Mortimer line had a superior one), but the key phrases were "God of his grace has sent me" and "to recover it... for default of governance." He presented himself as both divinely sanctioned and the saviour of the realm's laws and good government. The assembly roared its approval. The Archbishop of Canterbury, Thomas Arundel, took Henry by the hand and led him to the empty throne. Henry of Lancaster was now King Henry IV. His coronation followed swiftly on 13 October 1399, the feast day of Edward the Confessor, deliberately linking his new dynasty to the revered Anglo-Saxon saint-king.
A Precarious Legacy
The revolution of 1399 was a stark demonstration of the medieval concept of kingship. A king’s right to rule was not absolute. It was conditional upon his adherence to the law, his protection of his subjects’ property, and his ability to command the loyalty of the great magnates. Richard II had failed on all counts. His fall was not the result of a single battle but of a slow, corrosive loss of legitimacy that made his authority crumble at the first serious challenge.
Henry Bolingbroke, an astute and charismatic politician, masterfully exploited Richard’s weaknesses. He returned not as a foreign invader but as an aggrieved English nobleman defending his rights, a cause that the entire landed class could support. His rapid mobilization was possible only because the country was already primed for rebellion. Lords like Northumberland, Westmorland (the lord of Brattleby), and Willoughby de Eresby did not join him out of fear, but out of a shared sense of grievance and political necessity.
Yet, the precedent set in 1399 was a dangerous one. In seizing the throne, Henry IV had shown that an anointed king could be deposed. The problem of legitimacy would haunt the House of Lancaster for the next sixty years. The very men who helped him to the throne, the Percys, would later rebel against him, feeling he had not sufficiently rewarded them. The weak genealogical claim would be challenged by the House of York, leading directly to the bloody dynastic civil war that we now call the Wars of the Roses. The ghost of the deposed Richard, who would die in captivity at Pontefract Castle early in 1400, lingered over the new Lancastrian dynasty, a permanent reminder that a crown won by force might one day be lost by it. The choices made in the summer of 1399, by kings, dukes, and the local knights of shires like Lincolnshire, set England on a turbulent and violent path for the century to come.
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Sources & Further Reading
Primary Sources: Annales Ricardi Secundi et Henrici Quarti, in Johannis de Trokelowe... Chronica et Annales, ed. H. T. Riley (Rolls Series, 1866). (Part of the St Albans chronicle, details events from a monastic perspective). Creton, Jean, Histoire du Roy d'Angleterre Richard II, ed. and trans. by John Webb in Archaeologia, vol. 20 (1824). (An eyewitness account by a French knight in Richard's service). The Parliament Rolls of Medieval England (PROME), ed. C. Given-Wilson et al. (Leicester, 2005). [Online at: sd-editions.com/PROME]. Contains the official Record and Process of the 1399 deposition. Usk, Adam of, The Chronicle of Adam Usk, 1377-1421, ed. and trans. C. Given-Wilson (Oxford, 1997). (A crucial first-hand account by a lawyer involved in the events).
Secondary Sources: Given-Wilson, Chris. Chronicles of the Revolution, 1397-1400: The Reign of Richard II. Manchester: Manchester University Press, 1993. (A superb collection of translated primary sources with excellent commentary). Given-Wilson, Chris. Henry IV. New Haven & London: Yale University Press, 2016. (The most recent scholarly biography of the king). Mortimer, Ian. The Fears of Henry IV: The Life of England's Self-Made King. London: Jonathan Cape, 2007. (A highly readable and insightful analysis of Henry's reign, focusing on the psychological impact of the usurpation). Saul, Nigel. Richard II. New Haven & London: Yale University Press, 1997. (The definitive modern biography of Richard II, providing essential context for his fall). Saul, Nigel. The Three Richards: Richard I, Richard II and Richard III. London: Hambledon and London, 2005. (Offers a comparative perspective on Richard II's kingship). Swarby, D. M. 'The Estates of the Percy Family, 1416-1537'. Unpublished PhD thesis, University of Durham, 1968. (Details Percy landholdings, including in Lincolnshire). A History of the County of Lincoln: Volume 2 ('Victoria County History'), ed. William Page (London, 1906). [Online at: british-history.ac.uk]. (Provides details on the religious houses and political landscape of medieval Lincolnshire). Walker, Simon. The Lancastrian Affinity, 1361-1399. Oxford: Clarendon Press, 1990. (An essential study of the network of retainers and followers that formed the basis of Bolingbroke's power).