Denbigh was founded in the late thirteenth century following the conquest of north Wales, on the site of a previous Welsh residence, which is situated on a hilltop that looks over the Vale of Clwyd. Henry de Lacy was granted the lordship of Denbigh by Edward I in October 1282, with building work immediately beginning on the construction of the castle and town. It was built on a grand and impressive scale, which reflected its importance as the seat of one of the wealthiest baronies in Wales. Denbigh was briefly captured by the Welsh during the Madog ap Llywelyn rebellion in 1294, with further construction work carried out until de Lacy’s death in 1311. Ownership of the castle then passed to the latter’s son-in-law, Thomas, earl of Lancaster. Later in the century it was acquired by the Mortimer earls of March, and subsequently by Edmund, duke of York, the nephew of Edmund Mortimer, upon the latter’s death, in 1425.

Denbigh was the principal castle owned by Richard, duke of York, in north-east Wales. He is known to have visited on multiple occasions in the 1450s, but his preferred residence in the region was at Ludlow Castle in Shropshire. York may have travelled via Denbigh after the debacle at Ludford Bridge in 1459. His visit, if it took place, was only fleeting, as he quickly fled by ship to his Irish lordships, where he was safe from royal retaliation. At around the same time, orders were issued by the government of Henry VI for the confiscation of the duke’s estates, which included Denbigh. On 5 January 1460, Henry’s half-brother, Jasper Tudor, earl of Pembroke, was granted the constableship of the castle. However, the king’s officials were confronted with armed resistance from the inhabitants of Denbighshire. Jasper was therefore tasked with crushing the Yorkist rebellion in the region, with £333 allocated to him for retaining knights and men-at-arms. Yet gaining control of Denbigh Castle proved to be difficult, due to its formidable defences and the defiance of its garrison.

To accomplish this task, Jasper requested money and artillery from the king, which the latter authorised on 16 February. Over the course of the following week, a series of royal commands were issued to support the besiegers. Jasper was granted commissions of array to raise soldiers, workers for the transportation of ordnance, and all the moveable goods of the defenders of the castle. He was also permitted to give pardons to all members of the garrison, except for any who were English or Irish, or any Welsh men who had been outlawed. Jasper subsequently assembled a sizeable army for the siege, which was mostly recruited from the lordships of south Wales. The defenders eventually surrendered to his forces in the spring of 1460. Nevertheless, it had been a costly enterprise, as Jasper was afterwards assigned £1,666 to cover the expenses he had incurred.

Following the Yorkist victory and the capture of Henry VI at the Battle of Northampton later that year, the victors sought to gain control of strategic castles, including Denbigh. On 9 August, the keeper of the privy seal was ordered to write a letter to Jasper’s keeper at the castle, Roger Puleston, in the name of the king. The latter was to be informed that the duke of York was our ‘true liegeman and no traitor’, and to hand it over to his representatives. Understandably, Puleston refused to comply with this instruction and continued to hold it in the name of Henry VI. York appointed Robert Bolde as constable of the castle on 13 September but made no attempt to regain it. Later in February 1461, following his defeat at the Battle of Mortimer Cross, Jasper wrote a letter to him. He asked Puleston to remain resolute in holding Denbigh as ‘our especial trust is in you’. Five months he sent him another letter, requesting that he perform his ‘faithful diligence for the safeguard of it’, with money to be provided by the receiver of the lordship, Griffith Vychan, for the provisioning of the castle. Nonetheless, the castle had been recovered by the Yorkists by the end of the year, most probably by the forces of Sir William Stanley. The constableship was subsequently granted by Edward IV to Thomas Salesbury on 23 January 1466, and then to William, Lord Herbert, in the year after.

                Denbigh was periodically threatened by the outbreak of Lancastrian rebellions in the north-east of Wales. In 1466, rebels were active in the region, with a rebel force led by Sir Richard Tunstall seizing control of Holt Castle. This prompted John Tiptoft, earl of Worcester, to travel to Denbigh in November to reinforce the garrison. Two years later, Jasper Tudor landed near to Lancastrian-held Harlech with a small force and led a raid across Wales towards Denbigh. His army sacked and burnt the town, but apparently the castle itself was not attacked. Soon afterwards, Sir William Stanley secured the settlement with his forces from Chester. In 1479, Edward bestowed the earldom of March upon his eldest son, Prince Edward, with Denbigh thereafter administered by his council. Richard, duke of Gloucester, as Lord Protector granted the constableship to Henry Stafford, duke of Buckingham, in May 1483. However, the latter was executed for treason a short time later, with the office restored to Salesbury, who was placed in command of a garrison of twelve soldiers.

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