fitz William, Raymond (‘le Gros’) (c.1140–c.1190), third son of William fitz Gerald (eldest son of Gerald of Windsor, castellan of Pembroke, and Nesta, daughter of Rhys ap Tewdwr, king of Deheubarth, Wales), was the most capable military leader of the Anglo-Norman conquest of Ireland. Although he was one of the numerous Geraldines, Raymond le Gros was part of the household of Richard de Clare (Strongbow) (qv), earl of Strigoil, and often served as leader or constable of Strongbow's personal troops.
He was sent to Ireland in the summer of 1170 to prepare for the arrival of Strongbow, and landed at a point near Waterford. He was soon joined by Strongbow's uncle Hervey de Montmorency (qv), and began to raid the region around Waterford. He was attacked by a much larger force but emerged victorious with about 500 prisoners; the victory was marred, however, by the execution of the prisoners, against his wishes. He had gathered some 200 men; joined by Strongbow and another 1,000 soldiers, they attacked Waterford two days later, and Raymond is credited with finding the defensive flaw that allowed the city to be taken. He travelled with Strongbow and Diarmait Mac Murchada (qv), king of Leinster to Ferns and then to Dublin, where he took part in the battle that captured the city from the Ostmen.
Le Gros was then sent to Aquitaine as an emissary from Strongbow to the king, to placate Henry II (qv) after the death of Diarmait Mac Murchada. He returned to Ireland in time to be caught in the siege of Dublin by Ruaidrí Ua Conchobair (qv), king of Connacht, where he led the surprise attack that broke the siege and routed Ua Conchobair's army. For all his good service to Strongbow, Raymond le Gros was granted no lands in Leinster and had a falling-out with the earl, who refused to allow him to marry his sister Basilia, and would not make him constable of Connacht. Le Gros then left Ireland to join the king in Normandy. When Strongbow returned to Ireland, he faced a revolt within his own household as his troops demanded the return of Raymond as their leader, and he was forced to ask Raymond to return, and promised him marriage to Basilia.
Raymond returned to Ireland with a force of 200 men and stabilised a dangerously weak Anglo-Norman presence, leading a raid into the Déise territory of Waterford. He returned to Wales in 1174 after the death of his father, but returned to Ireland with a force of some 500 men to relieve Strongbow, who had been besieged in Waterford after a serious revolt by the Irish. He married Basilia before marching north to stabilise the Anglo-Norman position in Meath, and was then granted lands in Dublin and Wexford by Strongbow. In 1175 he led a force of 800 men against Domnall Ua Briain (qv), king of Thomond, captured and garrisoned Limerick, and returned to Dublin to face royal envoys sent to judge charges of treason levelled against him by Hervey de Montmorency. In 1176 le Gros returned to Limerick to end a siege of the city by Ua Briain and then marched south into Desmond to restore Diarmait Mac Carthaig (qv) to his throne. While in Desmond, he received news of Strongbow's death and returned to Dublin after abandoning Limerick. He acted as chief governor till the arrival of William fitz Audelin (qv), but fitz Audelin then seized his lands in Wexford and Dublin.
In 1182 le Gros sailed from Waterford to relieve the siege of Cork and free his uncle Robert fitz Stephen (qv). He inherited fitz Stephen's lands in Cork and was alive when John, lord of Ireland (qv), came in 1185. He died sometime before the end of the century and was buried in the abbey of Molene, near Youghal; his lands passed to his illegitimate son Richard, ancestor of the Carew family.