O'Connor, Roger (1763–1834), eccentric democrat, was born 8 March 1763, the fourth of five sons of Roger Conner (b. 1728) of Connerville, near Dunmanway, Co. Cork, and his wife Anne, daughter of Robert Longfield (1688–1765) of Castle Mary, near Cloyne, Co. Cork. The Conners were well connected with other protestant gentry in the county. Anne Conner's brother Richard was high sheriff (1758) and MP for various Cork boroughs until ennobled as Lord Longueville (1795). Roger the younger entered TCD (1777) but did not graduate, and was called to the Irish bar (1783) but did not practise. His father gave him a large part of his property (1783), and when his eldest brother, Daniel, left Ireland (owing, according to R. R. Madden (qv), to ‘a prosecution carried on against him’) he came into possession of Connerville (later renamed Carrigmore).
In early life he shared the tory principles of his family, belonged to the Muskerry Light Horse, and on one occasion captured seven Whiteboys who in consequence were hanged at Macroom and their heads spiked. In middle life he came to profess the democratic politics of his younger brother Arthur O'Connor (qv) and like him changed his surname to O'Connor. According to W. J. O'Neill Daunt (qv), whose father was a neighbour of Roger O'Connor's, he fortified Connerville to sustain an attack from government forces, while he gave money to drink the king's health to troops en route for Bantry Bay in December 1796. In the early months of 1797, Roger O'Connor was regarded as the leader of the local United Irishmen; he fled to England but returned to Ireland to surrender to a warrant for his arrest under emergency legislation (18 June). He was examined by the chief secretary, Thomas Pelham (qv), but allowed to return to Cork. There he attended the assizes and, by providing counsel for prisoners and spiriting away witnesses, effected their acquittal. A few days later, on an information sworn against him at the instance of his brother and neighbour Robert Conner of Fortrobert, he was arrested and imprisoned (27 September 1797–early April 1798). From Cork jail he was actively engaged in United Irish activity through couriers.
Arthur O'Connor later told Madden that Roger was the owner and chief writer of the Harp of Erin, a Cork paper intended to promote the United Irish cause in Munster; its tone was truculent and its run was brief (7–14 March 1798). Eventually acquitted, Roger O'Connor went to London, where he was rearrested (11 April); he claimed in a pamphlet, To the people of Great Britain and Ireland (1799), that the government dreaded his ‘power’ and his ‘inclination to give them opposition’. He was allowed to go to Maidstone to give evidence for his brother Arthur, on trial for high treason, but was not called (mid May). He was conveyed back to Dublin and committed to Newgate (2 June). Roger O'Connor accompanied his brother and other United Irish leaders to Fort George in Scotland to be held as a state prisoner (April 1799). Conditions were good. He was allowed to range outside the fort and have his wife and children to stay; he was released (25 December 1800) long before any other state prisoner and, on giving £9,000 bail, liberated (January or February 1801). Why he attracted the attention of the Irish and British governments and was held with United leaders, though not a United Irishman, is a matter for conjecture. Among the reasons may have been his social position, his connexion with Arthur O'Connor, his engaging personality and utter plausibility, the extravagance of his views and his indulgent attitude to the lower classes – R. B. Sheridan (qv), writing to his wife from Maidstone, described him as ‘one of the finest fellows I ever saw’.
When going into exile (1802) Arthur O'Connor gave Roger (who was allowed to return to Ireland) power of attorney to manage his Irish property (worth £1,200 p.a.), from which he expected income to be remitted; Roger, however, sold part of it and kept the proceeds (about £10,000); Arthur replaced Roger with their brother, Daniel, took protracted legal action against Roger, and many years later obtained some redress. After his release from Fort George and return to Ireland, Roger O'Connor purchased (1803) the lease of Dangan Castle, Co. Meath, the property of Richard Colley Wellesley (qv), 2nd earl of Mornington, brother of the future duke of Wellington (qv); he intended it to be a house fit for the reception of Bonaparte should he invade Ireland. In 1809, not long after it was heavily insured, the castle was destroyed by fire. It was rebuilt, and appears to have been used by O'Connor as a base from which to lead a gang of bandits to rob mail-coaches and commit other thefts, storing the booty in a vault or dividing it between his accomplices. This was what William John Fitzpatrick (qv) was told many years later by ‘a very truthful coachman’, a native of Dangan. On 5 August 1817, O'Connor was tried at the Meath assizes at Trim on a charge of being the principal agent in the robbery of the Galway mail-coach at Cappagh Hill, Co. Kildare, on 2 October 1812. The English radical Sir Francis Burdett came from England to attest to O'Connor's good character; O'Connor was acquitted amid great acclamation, almost immediately brought out a pamphlet denouncing the government, The eleventh conspiracy of the oligarchy of England and their Anglo-Irish agents (1817), and began criminal proceedings for perjury against one of the witnesses against him, Daniel Waring, a former accomplice. Waring was acquitted but had to leave Ireland secretly.
It would appear that after 1817 O'Connor's mental health was in decline. His next publication was Chronicles of Eri; being the history of the Gaal Sciot Iber, or the Irish people (2 vols, 1822), said to be ‘translated from the original manuscripts in the Phoenician dialect of the Scythian language’. It attempted to prove that the pagan civilisation of Ireland had been ruined by the advent of Christianity. Thomas Moore (qv), in his Memoirs of Captain Rock (1824), suggests that the name may have derived from the initials of ‘Roger O'Connor, King’. Six years later appeared O'Connor's Letters to his majesty, King George the Fourth, by Captain Rock (1828) decrying the modern nobility. During the last two or three years of his life Roger O'Connor resided again in County Cork, near Kilcrea, in the parish of Ovens. There he died, at Knockenmore Cottage, on 27 January 1834, attended on his deathbed by a catholic priest, David Croly, introduced by a young Kerry woman of humble origin (whom O'Connor believed to be of ancient Irish royal descent) who lived with him as his companion. Croly (b. 1780?), who was removed from his clerical office and placed under episcopal censure for publishing a pamphlet, An essay . . . on ecclesiastical finance (1834), found that O'Connor remained, as he had professed openly for many years, an unbeliever. At his own request O'Connor was buried at Kilcrea Abbey in the tomb of the MacCarthys, though he had no connexion with them.
He married firstly Louisa Anna, daughter of Col. Edmund Strachan of the 32nd regiment, by whom he had a son, Roderick, who settled in Van Diemen's Land, and a daughter, Louisa, who died unmarried; he married secondly (1788) Wilhelmina (d. 1808 or 1809), daughter of Nicholas Bowen (said to be of the family of Bowen of Bowenscourt, Co. Cork), by whom he had four sons. The third son of the second marriage was William O'Connor (1791–1871), later known as Francis Burdett O'Connor (qv) and an officer in the Bolivian army; the youngest son was Feargus O'Connor (qv), who died insane. Madden, a physician, wrote of Roger O'Connor: ‘his character will be found as curious a subject for investigation as can be desired by an inquirer into mental anomalies’.