Son of the first Norman-French Constable of Windsor Castle, and married to a Welsh Princess daughter of the King of Deheubarth, he was in charge of the Norman forces in south-west Wales.
[2]Gerald may have been born at Windsor Castle in Berkshire, then a strategically placed motte-and-bailey royal fortress and a principal royal residence, hence his sobriquet "de Windsor", although may have simply taken the name of the family seat as per tradition demonstrated by the de Barris of south Wales .
[5] Walter FitzOther, as his surname Fitz asserts, was the son of Otto Gherardini (Latinized to Otheus),[6] who had been Constable of Windsor Castle during the reign of King Edward the Confessor (r. 1042–1066).
The death in battle of Gerald's father-in-law, Rhys ap Tewdwr, Prince of Wales,[11] and the last king of Deheubarth[12] in Wales ("last king of the Britons"), was the opportunity for a general Norman invasion of South Wales during which Arnulf de Montgomery, youngest son of the powerful Roger de Montgomerie, 1st Earl of Shrewsbury, swept out from Shrewsbury and ravaged south into Dyfed, where he built Pembroke Castle, in the form of a rudimentary fortress later described by Giraldus Cambrensis (c.1146 – c.1223) (Gerald's grandson) as a "slender fortress of turf and stakes.
When he went back to England, Arnulf left the fortress and a small garrison in the charge of Gerald of Windsor, a stalwart, cunning man, his constable and lieutenant".
Giraldus Cambrensis described the events as follows: When they had hardly any provisions left, Gerald, who, as I have said, was a cunning man, created the impression that they were still well supplied and were expecting reinforcement at any moment.
Nest brought the manor of Carew as part of her dowry, and Gerald cleared the existing fort to build his own castle along Norman lines.
According to the Brut y Tywysogion, Owain and his men entered the couple's home (assumed by historians to have been either Cilgerran Castle or Little Cenarch) and set fire to the buildings.
Owain himself was obliged to go into exile in Ireland and when he returned in 1116, he was killed when his retinue of fifty men at arms was cunningly attacked by Gerald and his large cohort as they both traveled to aid the king of England.
As Gerald de Windsor makes no further appearance to that date in the "Annals" or in the "Chronicles of the Princes", the presumption is that he did not long survive his enemy, Owain ab Cadwgan, and that the Earl of Kildare's Addenda is erroneous in putting his death as late as 1135.