julesfrusher
Hugh Despenser (the even elder) - Rebellious Knight and England's Last Justiciar
Early Years
The grandfather of Hugh Despenser the younger was born around 1223 to another Hugh Despenser who was the steward of the earl of Chester. As is quite often the case we know nothing about his childhood or where he learned his skills at arms. What we do know however is that when he was around 15, in 1338, his father died. His father seems to have been in quite high favour with the king, Henry III, and his son seemed to follow in his footsteps as Henry sent Hugh several gifts in the following years, for example two casks of wine in 1245 and some wood for building in 1247. In 1249 he was granted free warren on his lands in Rutland.

During these years it is tempting to speculate that he was often at court as he certainly kept in Henry's good books. In 1255 he was appointed as the constable of Horston Castle, just north of Derby. Two years later he was again in royal company, this time accompanying Richard earl of Cornwall, Henry's brother to Aachen in Germany where the earl was to be crowned as King of the Romans.
It was probably during these years that Hugh met the man who played a large part in his life - and death - Simon de Montfort. Simon was some 15 years older than Hugh and had already had a chequered relationship with the king, but that didn't seem to deter the two men from becoming friends. The first mention of Hugh and Simon in the same record occurs in 1256 when Edmund de Lacy engaged them as negotiators in the arrangement of his son Henry's marriage to Margaret, daughter of William Longespee. This is the Henry de Lacy that became 3rd earl of Lincoln, one of the most powerful men in the country, and whose daughter Alice married Thomas, earl of Lancaster. Hugh Despenser is also mentioned as an executor of Simon de Montfort's will in 1259, an extremely trusted position which shows how close they must have become by them.
Despenser and De Montfort
All of this was at a time of great crisis in England for Henry III. Due to on-going debts, harsh money-raising practices and the rather bad behaviour of Henry's Lusignan relatives, the barons became rather fed up with how things were going. They pressured Henry into accepting what would later be known as The Provisions of Oxford - a series of measures aimed at reform. One of those measures was that a permanent council of 15 men (with only three to be chosen by Henry) would meet three times a year to advise the king and bring correction to anything they felt needed it. Simon de Montfort and Hugh Despenser were among those chosen but Simon, busy with his French estates, was away for most of the time. Henry towed the line and even the hated Lusignans left the country, but it was not going to last.

By 1260, the barons had relaxed their vigilance just enough that Henry tried to regain full power again but Simon was still critical of the king's attempts to assert control. So critical in fact that Henry called him forth to explain himself. Simon, however was saved from doing so by an uprising in Wales. Llywelyn ap Gruffydd attacked the English forces in South Wales and it wasn't until August that a truce was reached. By the Michaelmas parliament de Montfort had once again gained ascendancy and he and the other barons replaced the king's Justiciar, Chancellor and Treasurer. The position of Justiciar* was taken by Hugh Despenser, who also became Keeper of the Tower.
In 1261, Henry persuaded the Pope to annul the Provisions of Oxford. With Rome on his side Henry was once again powerful and decided to reverse other decisions made by de Montfort and his party. One of the first things he did was to remove Hugh Despenser (as well as the other men loyal to Simon) from their royal offices. Hugh was replaced as Justiciar by Philip Basset, his father in law. De Montfort was abroad from 1261 to 1263 but when he returned he was not very happy with all that had happened in his absence and especially with the discarding of the Provisions, which he truly believed in. He once again took up their cause along with several other disaffected barons including Despenser. The king retreated to the Tower while de Montfort and his allies attacked the estates of all those loyal to the Crown, including the Bishop of Hereford (who was a foreigner in their eyes). Hugh Despenser was once again made Justiciar of England.
Henry meanwhile, tried another tack, appealing to the king of France to arbitrate in the dispute (and taking himself overseas out of harm's reach). In January 1324 the French King awarded his decision to Henry that the Provisions of Oxford were indeed null and void and that the king should be able to appoint whoever he so wished to sit on council. Henry returned to England but if he thought the rebellious barons would now fall into line, he was very much mistaken. Simon and his followers were even more angry than before and set about with fresh vigour - attacking the king's supporters, notably one Roger Mortimer (grandfather to the Roger de Mortimer who had Hugh the younger executed) on the Welsh Marches. Hugh Despenser was also active during these attacks and led a group of Londoners in attacking the earl of Cornwall's manor at Isleworth. In April of that year there was a massacre of Jews in London by some of Simon's supporters; Despenser not only saved the lives of some who were being attacked, he also gave them shelter within the Tower.

In May there was a great battle at Lewes in Sussex where, despite being outnumbered, de Montfort and his men won the day, even capturing the king and his son, Edward. Hugh's father in law, Philip Bassett, fighting for the king, suffered over 20 wounds before surrendering to his son by marriage. Bassett was treated well in captivity though, probably at Hugh's insistence. It was after Lewes, however that things began to go wrong for de Montfort and his men. Henry's queen, the very capable Eleanor of Provence, fled to France and started to raise a mercenary army with plans to invade and rescue her husband. Despenser was given the task of ensuring the security of the eastern coastline just in case she succeeded. He was also sent to negotiate with both a papal legate and the king of France on de Montfort's behalf to try to forestall any such invasion.
Meanwhile, de Montfort's sons were beginning to cause problems by grabbing lands and powers for themselves - something Simon had always criticised Henry's Lusignan relatives for. This prompted a split in the Montfortian party as the powerful earl of Gloucester changed sides. To make things even worse, prince Edward escaped from confinement in May, joining up with de Clare and the lords of the Welsh Marches. Seeing an immediate threat, de Montfort and his lieutenants, including Hugh Despenser, rode out to quell the uprising. The end result was the Battle of Evesham.
Battle of Evesham
Simon had decided to briefly stop at Evesham to allow his troops some rest. He was not expecting Edward to arrive so quickly, so when he awoke on the morning of the 4th August he must have been astonished and shocked to find the prince occupying the centre ground on the uppers slopes of Greenhill - with Mortimer on his right and Gloucester on his left. More to the point, de Montfort was heavily outnumbered. Realising his dangerous predicament, Simon offered that any of his men who wished to leave could do so. To his close friend Despenser he is reported to have said:
My lord Hugh, consider your great age and look to saving yourself; consider the fact that your counsel can still be of great value to the whole country, for you will leave behind hardly anyone of such great value and worth.
Hugh, probably wondering why Simon would mention his great age (he was only about 42) when his friend was much older, replied (reportedly): 'My lord, my lord, let it be. Today we shall all drink from one cup, just as we have in the past.'
The ensuing fight was, in the words of one Robert of Gloucester: 'A murder of Evesham for battle it was none'. Edward picked out 12 men, including Roger Mortimer, to seek out de Montfort and kill him. Soon, de Montfort and his closest friends found themselves surrounded by enemy forces. Simon was unhorsed and even though he fought on foot, he was soon brought down. It was Mortimer who wielded the fatal blow. Next to him fell Henry his son and Hugh Despenser (also reputedly killed by Mortimer). Simon's body was beheaded and mutilated in a terrible manner; it is not recorded whether the same fate fell Despenser. Later, monks from nearby Evesham Abbey claimed the bodies of Henry de Montfort, Hugh Despenser and the headless torso of de Montfort and interred them before the High Altar. Later they were said to perform miracles of healing.

Today the Evesham Abbey that contained the bodies of de Montfort and Despenser is all but gone, destroyed in the Reformation. The bell tower is the only original feature that still stands. There is, however, a stone commemorating Simon de Montfort (but nothing for Hugh).
Marriage
Hugh Despenser married Aline Bassett, daughter and heiress of Philip Bassett around 1259/60. Considering that father in law and son-in-law ended up on opposite sides during the Barons' Wars it should be explained that, at first, Bassett was on the side of the reformers. In 1261 she gave birth to a son, Hugh, who would later be known as Hugh the elder, father to Hugh the younger, and she may also have had three daughters, namely Eleanor, Ann and Joan. I say 'may' because it is not absolutely clear that she was their mother. There is a chance that Hugh had a previous undocumented marriage and that the daughters come from that, although I think it unlikely that there are no records of this.
Aline must have found herself in a conflict of loyalties between her husband and father during the Barons' Wars but she seems to have served her husband well. At the time of the Battle of Evesham, Aline had been given control of the Tower and its prisoners. By a coincidence, later on in 1326, Eleanor, the wife of her grandson also had control of the Tower while her husband and the king fled from the invasion force of Queen Isabella and Roger Mortimer. After hearing of the battle's outcome, Aline sensibly threw herself and her children on her father's mercy and due to his loyalty to the king, was allowed to keep the Despenser lands for the inheritance of her son. Other rebel barons' widows were nowhere near as lucky. In 1271 she made a second marriage to Roger Bigod, soon to be earl of Norfolk and afterwards was known as Lady Despenser, Countess of Norfolk. Aline died in 1281.

* Justiciar - the chief minister of the king and dispenser of justice in the land. Also could represent the king when he was out of the country.