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Fitzosbern, Earl of Hereford, built the older parts in the eleventh century, but the most of Chepstow dates from that great epoch of castle-building on the Welsh border, the reign of Edward I. We are told that the second Fitzosbern was attainted and his estates forfeited, but that the king one Easter graciously sent to him in prison his royal robes.

The tyranny of Odo of Bayeux and William Fitzosbern, which provoked attempts at rebellion in 1067; the stand made by the house of Godwin in Devonshire in 1068; the attempts of Mercia and Northumbria to shake off the Normans in 1069 and 1070; the last struggle for independence in 1071, in which Edwin and Morcar finally fell; the conspiracy of the Norman earls in 1074, in consequence of which Waltheof perished all tended to the same result.

I have no doubt of the victory; we are come for glory; the victory is in our hands, and we may make sure of obtaining it if we so please. "As the Duke was speaking thus and would yet have spoken more, William Fitzosbern rode up with his horse all coated with iron. 'Sire, said he, 'we tarry here too long; let us all arm ourselves. Allons! allons!

Against this it was most important to guard; as the Conqueror learned from the events of the first year of his reign, when the severe rule of Odo and William Fitzosbern had provoked Herefordshire. Ralph Guader, Roger Montgomery, and Hugh of Avranches filled the places of Edwin and Morcar and the brothers of Harold.