After the rebellion in London, Bishop Henry returned to Winchester. Having defected, he now intended to rid his city of its remaining Angevin influence and immediately set about besieging the royal castle, held in Matilda’s name. The Angevins trapped inside now appealed to Matilda still at Oxford Castle. She arrived with her army on 31 July 1141, on a mission to relieve the castle. In the meantime, Bishop Henry had fortified his palace, Wolvesey, and escaped to Queen Matilda and the Royalists in London.
With Bishop Henry gone, Matilda and the Angevins entered the city of Winchester. They quickly relieved the royal castle and set to work on besieging Wolvesey. They could not have anticipated what happened next. The Royalist army, led by Queen Matilda and William of Ypres, surrounded the city walls thereby creating a double siege and cutting off vital lines of supply. The Angevins were now trapped and at the mercy of their enemies.
The situation was exacerbated when fire broke out in the city on 2 August, destroying homes, churches, two abbeys, and much of the royal castle. With limited shelter and supplies, the Angevins persevered until September when the decision was made to leave the city. On 14 September Robert launched a diversionary attack, allowing Matilda to safely flee Winchester with her escorts, Brian FitzCount and Reginald of Cornwall. King David of Scotland and his son, Henry – present at the siege – were next to follow. Miles of Gloucester escaped the city ‘half naked’ after shedding his armour to prevent identification. At the rear, however, Robert and the remainder of the Angevin army were pursued by the Royalists. Separated from their allies, they had no choice but to turn around and fight.
Matilda was now en route to the safety of Gloucester castle. A sense of urgency dictated that she abandon the traditional female pose of riding side-saddle and she soon entered the county of Wiltshire. She made two overnight stops here, first at Ludgershall and then at Devizes. According to myth, Matilda hid in a coffin to complete the final leg of her journey to Gloucester, but she was in fact so exhausted that she had to be carried on a litter by two horses. It did not take long for the latest news from Winchester to spread and reach the Angevin camp. The Rout of Winchester had been a complete failure and the Royalists had captured Robert of Gloucester.
News of Robert’s capture was a tremendous blow to Matilda and her followers. Robert was a central figure in the Angevin camp and negotiations for his release commenced immediately. Matilda had a bargaining tool in Stephen, still incarcerated at Bristol, but the discussions were lengthy and complex. An agreement was finally reached and an exchange of prisoners arranged. On 1 November 1141 Stephen was released from Bristol, with Robert following two days later. The Angevins were also allowed possession of the castles at Oxford and Devizes. Giving Stephen his freedom came at a price to Matilda – he was now free to resume his reign in England.