Outlaw (Outlagh, Outlawe, Utlagh, Utlawe), Roger (d. 1341), deputy justiciar and chancellor of Ireland and prior of Kilmainham, was from an Anglo-Irish family who held lands in Kilkenny. He first appears as prior of the Hospital of St John of Jerusalem in Ireland on 1 August 1317. Later that year, during the height of the Bruce invasion, he acted briefly as keeper of the treasury during the absence of Walter Islip (qv). His valuable service to the crown against the Scots was recognised by Edward II in August 1318 when the Hospital was granted Chapelizod and was given licence to acquire substantial lands in mortmain. In the same year Outlaw was also enfeoffed with lands in Kildare by the earl of Kildare, Thomas fitz John FitzGerald (qv).
He was appointed chancellor of Ireland 4 January 1322 and had custody of the seal 16 April 1322–14 May 1331. After the escape of Roger Mortimer (qv), Outlaw was sent to England in September 1323 to warn the king of the dangers posed to the lordship by Mortimer and the willingness of some of his adherents in Ireland to take up his cause; Outlaw was also to try to persuade the king to come to Ireland in person. He acted as deputy justiciar from July to October 1324, and again (1–12 May 1327) during the absence of John Darcy (qv). That summer, as the activities of Robert Bruce and his overtures towards Ulster were causing alarm, Outlaw was sent north to negotiate with the magnates there and ensure their continuing allegiance to the crown. In September 1327 he was ordered to be before the king and his council to explain the charges recently levelled against Maurice fitz Thomas FitzGerald (qv), earl of Desmond. The following month Edward II, in consideration of his loyal service, pardoned the Hospital of a large part of its debt to the exchequer.
After Kildare's death the king's Irish council made Outlaw acting justiciar from 6 April 1328 to May 1329. Between July and August 1328 he was in Munster, attempting to quell disturbances there. His position became particularly vulnerable during the stormy Alice Kyteler (qv) affair, despite an apparent attempt to withhold his support from Kildare, who, before his death, had taken vigorous action against Richard Ledrede (qv), bishop of Ossory, who had accused Kyteler of sorcery and other crimes. Roger's prominence in finding £1,000 security for the release of his kinsman, William Outlaw (qv), Kyteler's son, drew the ire of Ledrede, who accused him of terrible heresies. In January 1329, however, he was completely cleared by a panel of churchmen at Dublin.
In April that year Outlaw held a parliament at Dublin and succeeded in extracting, from all the magnates who attended, promises to control and discipline their followers. In August, after a parliament at Kilkenny, he accompanied the earls of Ulster and Ormond (William de Burgh (qv) and James Butler (qv)) on an unsuccessful expedition against Brian Ó Briain (qv). He imprisoned Desmond after his indictment at Cashel and also placed the earl of Ulster in custody. He acted as deputy justiciar again (7 July 1330–2 June 1331), and between October 1331 and August 1332 he was at court.
Appointed chancellor of Ireland once more on 30 September 1332 (a post he occupied from 14 November 1332 to 14 August 1337), he was chosen as the central figure in Edward III's new approach to Ireland in preparation for the king's proposed visit. Outlaw was entrusted with opening negotiations with all those who were in rebellion against the crown, both native Irish and Anglo-Irish, and he was to report the results of these directly to the king. In addition, he was also granted some discretionary powers with regard to the vexed issue of pardons. He was twice commissioned as deputy justiciar in 1335 (15 March–26 June; 28 August–18 September) and that year led an expedition to Ulster; there, with the assistance of Edmund de Burgh (qv), he consulted a number of the Irish chiefs in an effort to induce them to take part in a royal campaign in Scotland. He was also successful in persuading the Irish chiefs of Leinster and those of the midlands.
He was deputy justiciar again (15 November 1336–15 October 1337), keeper of the great seal from 2 September 1338 till his death, and deputy justiciar for the final time from 8 April 1340 to 5 February 1341. In June 1338 on his order's behalf he loaned the king a substantial sum to help finance an expedition to Flanders, in return for which the Hospital was rewarded with the manor of Leixlip in fee farm. In August the same year he was appointed to assist the justiciar and undertake a regular survey of the Irish exchequer. He died 6 February 1341 at the Hospital's preceptory of Any in Co. Limerick and was buried in the chapel there.
Outlaw was probably the best-known of the priors of Kilmainham; his ordinances have been preserved in detail in the Register of Kilmainham. He was remarkably adept politically; one of the longest-serving officials in the Irish administration during the fourteenth century, he had little difficulty in serving under two kings and the Mortimer regime, and was completely trusted by each. He also appears to have made few enemies among the competing factions in Ireland: he was, for example, one of the executors of the earl of Ulster's will in 1333. According to Clyn, ‘he was a prudent and gracious man who by his industry and the special favour of the king acquired for his order many possessions, churches and lands’.