The year 1399 stands as a watershed in English history, a moment when the seemingly immutable principle of divinely ordained monarchy shattered against the rocks of noble ambition and political reality. The deposition of Richard II, the last undisputed Plantagenet king in the direct male line, and the usurpation of the throne by his cousin, Henry Bolingbroke, Duke of Lancaster, was not merely a palace coup. It was a constitutional earthquake whose aftershocks would be felt for a century, culminating in the brutal dynastic struggle known as the Wars of the Roses. This dramatic transfer of power was a saga of personality, property, and principle, with its roots deep in the soil of England, not least in the vast and powerful estates of the Duchy of Lancaster that dominated counties like Lincolnshire.
A Sun King’s Shadow: The Troubled Reign of Richard II
To understand the rupture of 1399, one must first grasp the character of the king who was overthrown. Richard of Bordeaux came to the throne in 1377 as a boy of ten, grandson of the great Edward III. His early reign was marked by the turbulence of the Peasants’ Revolt in 1381, where the young king showed remarkable courage in facing down the rebels at Smithfield. This moment, however, instilled in him a profound sense of his own regal majesty and a deep-seated distrust of both the common mob and the overmighty magnates who had failed to control them.
As Richard came of age, his style of kingship proved deeply divisive. He cultivated a court of unprecedented magnificence, centred on the Palace of Westminster, and fostered an ideology of sacred kingship that placed him far above his subjects, even the greatest lords. His chosen emblem, the White Hart, and his promotion of a highly personal and artistic court culture were attempts to project an image of divinely sanctioned, absolute authority.
This exalted view of monarchy clashed violently with the political realities of late 14th-century England, where powerful nobles, particularly the king's own uncles, expected to play a significant role in governance. The first major crisis erupted in the late 1380s with the rise of the Lords Appellant. A group of powerful magnates—including the king’s uncle Thomas of Woodstock, Duke of Gloucester; Richard FitzAlan, Earl of Arundel; and Thomas de Beauchamp, Earl of Warwick—accused the king’s favourites of treason and effectively seized control of government. Crucially, they were joined by two younger men: Thomas Mowbray, Earl of Nottingham, and the king’s own cousin, Henry Bolingbroke, son of the immensely wealthy John of Gaunt, Duke of Lancaster. In the ‘Merciless Parliament’ of 1388, this faction purged Richard’s court, executing or exiling his closest companions.
Richard never forgave this humiliation. For nearly a decade, he bided his time, ruling with apparent moderation. But in 1397, he struck back with breathtaking speed and ruthlessness. He had Arundel executed, Warwick imprisoned, and his uncle Gloucester murdered while awaiting trial at Calais. This period, often termed Richard’s ‘tyranny’, saw the king rule by fear, using a loyal Cheshire guard to intimidate opponents and raising forced loans without parliamentary consent. He seemed to be deliberately dismantling the traditional checks on royal power.
The Lincolnshire Connection: The Powerhouse of Lancaster
Central to this entire drama stood the colossal power of the House of Lancaster, and by extension, its heartlands in northern and eastern England. Henry Bolingbroke was no mere courtier; he was the heir to the greatest private inheritance in the kingdom. The Duchy of Lancaster, created for his father John of Gaunt, was a palatinate—a state within a state—with its own administration, courts, and vast revenues.
In Lincolnshire, the Lancastrian footprint was immense. Bolingbroke Castle, Henry’s birthplace in 1366, was a formidable military and administrative centre. But the duchy’s influence extended far beyond this single fortress. It held the Honour of Bolingbroke, a vast swathe of manors and lands across the county. The thriving port of Boston, a key hub for the wool trade, was under Lancastrian control, as were significant properties within the city of Lincoln itself. Manors from Sutton to Wrangle, and from Thoresby to Ingoldmells, all paid their dues to the Duke of Lancaster. The Barony of Brattleby, though held by others, existed within a county where Lancastrian affinity and power were the dominant political force.
This network of land was buttressed by a network of men. John of Gaunt, and later Henry, maintained a large retinue of knights, esquires, and administrators bound to them by fees and loyalty. In Lincolnshire, families like the Swynfords of Kettlethorpe were inextricably linked to the Lancastrian cause. Sir Thomas Swynford, Henry Bolingbroke’s half-brother through his father's controversial third marriage to Katherine Swynford, was a key Lancastrian retainer and a powerful figure in the county. When Bolingbroke made his move, he could count on the men of the Lincolnshire fens and wolds, whose loyalties had been cultivated over generations. Richard II’s actions against Henry were not just an attack on a cousin; they were a direct challenge to the most powerful magnate interest in the kingdom, an interest with deep and abiding roots in Lincolnshire.
The Fatal Error: Disinheritance and Invasion
The final act was set in motion by two fateful events. In 1398, Richard resolved the simmering tension between the two remaining Lords Appellant, Henry Bolingbroke and Thomas Mowbray. At a tournament, he intervened to prevent their trial by combat, exiling Mowbray for life and Bolingbroke for a period of ten years (later reduced to six). Crucially, Richard promised his cousin that his inheritance would be secure.
On 3 February 1399, John of Gaunt died. Richard II, in desperate need of funds for his upcoming expedition to Ireland and keen to neuter the Lancastrian power base forever, made a catastrophic decision. Citing Bolingbroke’s status as a traitor, he broke his solemn promise and, with the approval of a cowed council, cancelled the legal documents that would have allowed Henry to claim his inheritance. Richard confiscated the entire Duchy of Lancaster for the Crown.
This act of disinheritance was Richard’s undoing. It was a flagrant violation of the property rights upon which the entire aristocratic order was based. If the king could seize the lands of the greatest duchy in the realm, then no nobleman’s inheritance was safe. Support for Richard, already thin, evaporated. He had united the entire landowning class against him in a bond of fear.
Compounding this error, Richard departed for a campaign in Ireland in May 1399, leaving the kingdom under the shaky authority of his aged uncle, the Duke of York. He had effectively left the door not just unlocked, but wide open.
Henry Bolingbroke, now styling himself Duke of Lancaster, saw his chance. With a small force, funded by the King of France, he set sail from Boulogne. Around 4 July 1399, he landed at Ravenspur, a now-lost port on the Humber estuary, strategically close to his estates in Yorkshire and Lincolnshire. His stated aim was not to seize the throne, but merely to reclaim his rightful inheritance—a brilliant piece of propaganda that won him immediate and widespread support.
The most powerful magnates of the north, Henry Percy, Earl of Northumberland, and his fiery son, Henry ‘Hotspur’ Percy, immediately joined him. Their adherence was critical, delivering the military power of the north into Bolingbroke’s hands. As Henry marched south, his army swelled. The Duke of York, the kingdom’s regent, raised an army to oppose him but found his men unwilling to fight the popular duke. York’s force disintegrated, and he too soon defected to his nephew’s cause. Within weeks, England had fallen to Henry Bolingbroke without a single major battle being fought.
The Capture of the King
News of the invasion reached Richard in Ireland late and piecemeal. By the time he landed with his army at Milford Haven in Wales around 24 July, it was too late. His kingdom was lost. His support melted away as his troops deserted, many flocking to join Bolingbroke, who was now at Bristol, where he had executed several of Richard's remaining loyal councillors, including William Scrope, Earl of Wiltshire.
Richard retreated into the mountains of North Wales, taking refuge in the mighty castles of Edward I. It was here that the final, pathetic act of his reign played out. The Earl of Northumberland was dispatched by Henry to negotiate with the king. According to the chronicler Adam of Usk, who provides a vivid, if partisan, account, Northumberland swore a sacred oath on the host in a chapel that Richard would be restored to his royal power if he would only agree to a trial for his unpopular councillors and return the Duchy of Lancaster to Henry.
Richard, desperate and isolated, agreed. He rode out from Conway Castle to meet with Henry, only to be ambushed by Northumberland’s men and taken under guard. His royal standard was torn down. He was now a prisoner. The meeting between the two cousins at Flint Castle has become iconic. The Kirkstall Chronicle relates how Henry, steel in his eyes, bowed low three times, but greeted his king with the chilling words, “My lord, I have come before you have sent for me… I have come to help you govern the kingdom, which you have governed badly for twenty-two years.” Richard was escorted to London, subjected to the humiliation of public mockery as he was paraded through the streets he had once dominated.
A Crown Claimed in Parliament
Henry Bolingbroke now faced a constitutional dilemma. He had the king, the kingdom, and the power. But how does one legally depose an anointed sovereign, God’s chosen representative on Earth? Outright murder was dangerous, and simply imprisoning Richard would leave a permanent focus for rebellion. Usurpation required the veneer of legality.
A parliament was summoned in Richard’s name to meet at Westminster on 30 September 1399. Henry’s lawyers and supporters worked feverishly to build a case. A deputation was sent to the captive king in the Tower of London, where he was allegedly persuaded to ‘voluntarily’ abdicate. A formal document was drawn up, in which Richard supposedly renounced all his rights to the throne, absolved his subjects of their allegiance, and declared himself "utterly insufficient and useless." The chroniclers report a poignant, theatrical scene where Richard, looking at his reflection, lamented how his sorrows had marred his face, before handing over his royal signet ring to Henry.
The next day, in a packed Westminster Hall, this "abdication" was read aloud. To bolster the case, a list of thirty-three ‘Articles of Deposition’ was also proclaimed, cataloguing Richard's crimes against the realm. These included his tyrannical actions against the Lords Appellant, his breaking of his coronation oath, his extortion of money, his declaration that the law was "in his own breast," and, critically, his unjust seizure of the Duchy of Lancaster.
With Richard thus formally and 'legally' removed, the throne was vacant. At this dramatic moment, Henry Bolingbroke rose from his seat, made the sign of the cross, and staked his claim to the throne in English, not the customary French:
“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 hath 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.”
Henry’s claim was a masterful, if legally dubious, trinity of justifications: a tenuous claim through a distorted Lancastrian genealogy, the undeniable right of conquest, and the acclamation of the people and Parliament, who now hailed him as king. The Archbishop of Canterbury took him by the hand and led him to the empty throne. Henry IV was king.
The Aftermath: A King in Pontefract and an Uneasy Crown
The story was not quite over. A deposed king remains a threat. Richard II was spirited away to the formidable Lancastrian stronghold of Pontefract Castle in Yorkshire. His fate was sealed in January 1400 when a group of his loyal supporters, the Earls of Salisbury, Kent, and Huntingdon, launched a rebellion known as the ‘Epiphany Rising’. The plot was to murder Henry IV and his sons at Windsor and restore Richard.
The rising was quickly and brutally crushed, but it proved to Henry that as long as Richard lived, his throne would never be secure. Shortly thereafter, likely around 14 February 1400, Richard died at Pontefract. The official account, advertised by the Lancastrian government, was that he had starved himself to death after hearing of the failure of the rising. However, contemporary chronicles and modern historians are divided. Adam of Usk claims he was starved to death by his keepers, while others hint at a more direct murder on Henry's orders. The examination of his skull in the 19th century revealed no conclusive marks of violence, lending some credence to the starvation theory, though whether it was self-inflicted or enforced remains a dark mystery.
Henry IV’s reign was plagued by the consequences of his usurpation. He faced repeated rebellions, from the Welsh under Owain Glyndŵr to the Percys who had helped him to the throne but felt inadequately rewarded. The crown he had seized sat uneasily on his head.
The events of 1399 established a perilous precedent: that a king who alienated his great magnates and violated the perceived rights of property could be overthrown and replaced by a more suitable candidate with the backing of Parliament. It fundamentally altered the English constitution, elevating the role of Parliament and the nobility in making and unmaking kings. While Henry IV and his son Henry V would hold the throne for the House of Lancaster, the flaw in their title—the memory of the deposed and murdered Richard II—would be exploited by the rival House of York fifty years later, plunging England into the Wars of the Roses and drenching the kingdom in blood. The dramatic fall of a king and the seizure of a crown in 1399 was not an end, but the beginning of a long and tragic new chapter in English history.
Sources & Further Reading
Primary Sources:
Adam of Usk. The Chronicle of Adam Usk, 1377-1421. Edited and translated by C. Given-Wilson. Oxford: Clarendon Press, 1997. (A vital, though biased, eyewitness account.) Froissart, Jean. Chronicles. Translated by Geoffrey Brereton. Harmondsworth: Penguin, 1978. (Provides narrative context for the earlier part of the reign and the duel at Coventry.) Given-Wilson, Chris, ed. The Kirkstall Abbey Chronicles. Oxford: Clarendon Press, 1999. (Contains a valuable narrative of the "Lancastrian Revolution".) Given-Wilson, Chris, ed. Chronicles of the Revolution, 1397-1400: The Reign of Richard II. Manchester: Manchester University Press, 1993. (An excellent collection of primary source extracts.) The Parliament Rolls of Medieval England* (PROME). Edited by Chris Given-Wilson et al. Woodbridge: Boydell Press, 2005. (Contains the official parliamentary record of the deposition.)
Secondary Sources:
Harriss, G.L. Shaping the Nation: England 1360-1461. Oxford: Clarendon Press, 2005. (An authoritative overview of the period.) Mortimer, Ian. The Fears of Henry IV: The Life of England's Self-Made King. London: Jonathan Cape, 2007. (A compelling biographical study of Henry IV, focusing on the psychological pressures of his reign.) Saul, Nigel. Richard II. New Haven: Yale University Press, 1997. (The modern scholarly standard for the life and reign of Richard II.) Saul, Nigel. The Three Richards: Richard I, Richard II and Richard III. London: Hambledon and London, 2005. Somerville, Robert. History of the Duchy of Lancaster, Vol. 1: 1265-1603. London: Chancellor and Council of the Duchy of Lancaster, 1953. (The definitive history of the Lancastrian estates and administration.) Swabey, F. "The English Nobility and the Deposition of Richard II." In Richard II: The Art, Spectacle and Politics of Late Medieval Court Culture, edited by N. Saul, 159-174. The Boydell Press, 2009. Victoria County History: A History of the County of Lincoln*. Various editors and dates. (Provides detailed local history on manors and landholding patterns in Lincolnshire, including those of the Duchy of Lancaster.)