Updated: Feb 16, 2022
Chepstow Castle played a part in the life of both Hugh Despensers. Built originally in 1067 by, it passed through the hands of the Fitz Osberns, the de Clares, the Marshalls and the Bigods, Earls of Norfolk. A large, sophisticated structure, it was an important link in the chain of defence of the Welsh Marches. When Roger Bigod died in 1306, the castle passed into royal hands.
From 1308 to 1310, Edward II gave the custody of it to Hugh Despenser (the elder). There are no records to show whether Hugh was there much or whether he left all of the administration to his deputy, John de Tany. Nevertheless, Hugh seemed to take his new position as constable seriously: accounts show that he was responsible for making extensive repairs to the building. This is surprising as Bigod had carried out major building works at the castle. However it seems from these records that while he was constructing new buildings, he must also have been ignoring the castle’s basic structure as a whole. It certainly seems that the roofs were in a bad state, as oak planks were brought in from the Wentwood - possibly for their repair. Also, the springalds (machines for throwing rocks - a bit like a catapult) needed replacing - most of the originals had been taken from their defensive positions and placed into storage where they were later discovered to be broken. In August 1310, Hugh was replaced as constable by Robert Darcy.
When Darcy took over the constableship, he must have had some questions about Despenser's and de Tany's time at the castle for, on October 1st, 1310, an inquisition was ordered by the king into what had happened regarding trespasses, and also the on-going disrepair of the building and estate:
Commission to John ap Adam, Master John Martel and John de Pateshulle to enquire whether Hugh le Despenser, to whom the custody of the castle of Struguyl [or Strugoil] and town of Chepstowe had been committed, granted during the time he held the custody any trespasses of vert and venison in the parks and woods of the eastle; also to report on any defects in the castle of Struguyl and Turegi and manors of la Planteland, Tudenham and Berton, the weir, and the fencing of the park, what men Hugh le Despenser had placed on the works of the castles and manors, and what the works were.
The Calendar of Inquisitions Miscellaneous has the outcome of the commission recorded on October 10th 1310 and reports de Tany's answers to the accusations of wrongdoing:
John Tauny, late warden of the castle of Strugoill and town of Chepstow, received the said castle in bad condition, the buildings being ruinous and uncovered; he much amended it, but to what value the jurors know not ; he committed no destruction of the woods, but caused charcoal to be made for the king's profit; he was not guilty of any extortions against the tenants.
After this, the castle officially passed to Thomas of Brotherton until 1323 when he sold it to Hugh Despenser the younger for the term of his life. It has to be said the amount paid was quite small and it is possible that the king 'persuaded' his brother to give it up to his favourite so cheaply. The possession of Chepstow castle now meant that Hugh was not only Lord of Glamorgan, but he was also now Lord of Striguil (the old name for Chepstow). It may have been a small gain but it was yet another important piece to add to his growing Welsh empire.
Chepstow also played a small but important role in the autumn of 1326, when Queen Isabella and Roger de Mortimer invaded England. Fleeing before the hostile army, Hugh and Edward went to Chepstow Castle, maybe hoping to hold it as part of a Royalist defence (Bristol was being held by Hugh senior while Caerphilly was commanded by Hugh’s son, Hugh). However, seeing that Welsh support was not forthcoming, Hugh and Edward then sailed from Chepstow out into the Bristol Channel. Where they were planning to go is a matter for speculation but bad weather forced them to put in to Cardiff, and soon after they were captured by Isabella and Mortimer’s forces.