fitz Stephen, Robert (c.1115–c.1185), son of Stephen, constable of Cardigan castle, and Nesta, daughter of Rhys ap Tewdwr, king of Deheubarth, Wales, was one of the prominent figures of the Anglo-Norman conquest of Ireland. He inherited his father's position as constable of Cardigan and spent much of his career defending Pembrokeshire from the advances of the Welsh. In 1157 he joined Henry II's expedition into Wales, narrowly escaping death in an ambush that killed his half-brother, Henry fitz Henry. In 1166 he was captured by Rhys ap Gruffydd at Cilgerran and spent three years as a prisoner. He was released in 1169 at the request of his half-brother Maurice fitz Gerald (qv), when they promised to go to Ireland to fight on behalf of Diarmait Mac Murchada (qv), king of Leinster.
Fitz Stephen led the first significant force of Anglo-Normans to Ireland, and landed at Bannow Bay on 1 May 1169. His force, which consisted of 36 knights, 60 men-at-arms, and 300 foot soldiers, was joined two days later by a smaller force led by Maurice de Prendergast (qv). Fitz Stephen and Prendergast attacked Wexford and captured the town, which Mac Murchada then granted to fitz Stephen to hold with Maurice fitz Gerald. Fitz Stephen accompanied Mac Murchada on a campaign into Osraige (Kilkenny) and then north into Uí Fáeláin and Uí Muiredeaig (Kildare and south Co. Dublin) to assert Mac Murchada's claims of overlordship. They then returned to Ferns, fortified it, and negotiated a peace with Ruaidrí Ua Conchobair (qv), king of Connacht. The defection of Prendergast to Domnall Mac Gilla Pátraic (qv), king of Osraige, was somewhat balanced by the arrival of Maurice fitz Gerald with reinforcements. Fitz Stephen was part of a campaign against Mac Gilla Pátraic in Laois, but then returned to Wexford while Mac Murchada and fitz Gerald went to Dublin. Fitz Stephen was then sent by Mac Murchada to aid Domnall Ua Briain (qv), king of Thomond, against incursions by Ruaidrí Ua Conchobair.
Although there is evidence that fitz Stephen had poor relations with ‘Strongbow’ (Richard de Clare (qv), earl of Strigoil), he accepted Strongbow's leadership after the earl came to Ireland, arriving at Waterford just after Strongbow had taken the city. He remained to defend Wexford while Mac Murchada and Strongbow marched on Dublin, but was tricked into surrender by the false rumour of Strongbow's death. He remained in the custody of the Ostmen of Wexford till October 1171, when the Ostmen gave him to Henry II (qv), who imprisoned him and revoked his grant of Wexford, but soon released him and recruited him into the royal household (although without restoring Wexford to him). He was placed into the garrison of Hugh de Lacy (qv) in Dublin when the king left Ireland, and granted land in Uí Fáeláin by the king; he was summoned to serve the king in Normandy in 1173, but joined the royal forces in England to put down a rebellion there.
He returned to Ireland in the company of William fitz Audelin (qv) in May 1176, but fitz Audelin confiscated the lands that had been given to him in Uí Fáeláin. Fitz Stephen was recalled to England with fitz Audelin (January 1177) and was present at the council of Oxford in May, where he and Miles de Cogan (qv) were given a speculative grant of the kingdom of Desmond. They took advantage of a war between Thomond and Desmond to capture part of Desmond, and in 1178 Diarmait Mac Carthaig (qv), king of Desmond, confirmed their overlordship of all of Desmond. Fitz Stephen and de Cogan drew lots to divide their cantreds; fitz Stephen received the eastern portion of their lands, and shared the custody of the city of Cork. He made his caput in Imokilly and started the process of subinfeudation. Mac Carthaig led a revolt that killed Miles de Cogan and fitz Stephen's son Ralph fitz Robert, who had married de Cogan's daughter, and fitz Stephen was besieged in Cork till relieved by his nephew Raymond fitz William (qv).
Fitz Stephen was greatly admired by his nephew Gerald of Wales (qv), who describes him as a well-built, sturdy man who lived well, but had an excessive fondness for wine and women. Giraldus also claims that fitz Stephen had been offered Mac Murchada's daughter Aífe (qv) in marriage before Strongbow, but refused because he was already married; but this is probably an invention by Giraldus to explain why his Geraldine kinsmen were not better rewarded for their heroics. It is notable that the first leader of the Anglo-Normans in Ireland had to wait so long for a permanent grant of land, and then had no children to whom to pass it. After his death (c.1185) his lands passed to Raymond fitz William.