Kenilworth was founded in the early twelfth century by Geoffrey de Clinton, who served as chamberlain to Henry I. It initially consisted of a keep and a bailey, which was accessed via a causeway through a massive lake. Following the death of his son and heir, also called Geoffrey, in 1175, the castle passed into royal ownership. Major works were carried out during the reigns of Henry II and King John, which greatly expanded its extent through the construction of the outer ward, and the heightening of the dam. Henry III granted the lordship to his brother-in-law, Simon de Montfort, earl of Leicester, in 1244, but the two men later fell out, which led to the outbreak of civil war during which the castle was subjected to a protracted siege in 1266. Henry then granted Kenilworth to his younger son Edmund, who was given the title of earl of Lancaster. It remained with his descendants until the death of Henry of Grosmont, duke of Lancaster, in 1345. Kenilworth was then acquired by his son-in-law John of Gaunt, a younger son of Edward III. Gaunt was responsible for transforming the castle into a palatial residence, through rebuilding the great hall, apartments and kitchens on a grand scale. Kenilworth became a royal castle following the accession of his son, Henry IV, to the throne in 1399. It thereafter became one of the most popular residences of the Lancastrian kings.

Kenilworth was a favoured residence of Henry VI who frequently visited and stayed at the castle during his reign. During times of crisis it also proved to be a secure place of refuge, such as in 1450 when the king fled London upon the approach of the rebels of Jack Cade. It was also used as an arsenal for the royal artillery, with guns sent there from the Tower of London in 1456-7, to combat the depredations of Sir William Herbert and Sir Walter Devereux who had carried out rebellious acts in Wales and Herefordshire. Worsening relations with the Yorkist lords prompted the king and the court to spend longer periods in Kenilworth in the late 1450s. It was subsequently alleged that the Yorkists took up arms in 1459 with the intention of launching a surprise attack against the castle to seize Henry. This plan was foiled by royalist countermeasures and the eventual flight of the Yorkist lords from Ludford Bridge later that year. Yet their success in fleeing to their overseas possessions in the Pale of Calais and Ireland meant that they continued to pose a danger to the safety of the realm. This prompted the carrying out defensive measures throughout the kingdom. According to the chronicler John Benet, at a royal council in the summer of 1460 it was decided to improve the fortifications of Kenilworth. It appears to be in this period that the outer defences were adapted to withstand artillery, through the construction of a gun tower and bulwark. Forty cartloads of guns and other ordnance was also sent from the arsenal at the Tower of London to the castle.

Yet following the Lancastrian defeat at the Battle of Northampton on 10 July 1460, Kenilworth was occupied by the Yorkists. Two men, Thomas Higford and William Vale, were subsequently reimbursed by Edward IV for their expenses in garrisoning and provisioning the castle. Later in 1471, according to the newsletter of a Hanseatic merchant, Gerhard von Wesel, Edward IV laid siege to the castle for eight days with his forces, following his return to the kingdom that year. After Edward’s resumption of power, the constableship of Kenilworth was granted to William Parr, who carried out substantial repairs to the castle at the king’s command. Following Parr’s death a few years later, the office was granted to Sir William Mountford. He held the constableship until the accession of Henry VII 1485, when it was granted to Matthew Baker. Kenilworth became one of Henry’s favourite residences, which he frequently visited. It was during one of these visits, in June 1487, that he received news of the landing of the army of Lambert Simnel.

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