Ludlow Castle was one of the key Marcher strongholds contested during the Anarchy. In 1138 it was held by Joce de Dinan for King Stephen. Geoffery Talbot besieged it for Empress Matilda. Stephen came to relieve it and a notable incident occurred: Prince Henry, later Henry II, was trapped by a hook and chain during the fighting and had to be rescued. The castle remained royalist for much of the conflict.
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