O'Leary, John (1830–1907), nationalist and journalist, was born in Tipperary town on 23 July 1830, son of John O'Leary (d. 1848), merchant, and his second wife, Margaret (née Ryan). By his first marriage the elder O'Leary had a son and three daughters; his second marriage produced two sons, John and Arthur (1833–61), and one daughter, the poet Ellen O'Leary (qv) (1831–89). Margaret died in the mid 1830s and her three children were brought up by an elderly aunt; they remained emotionally close all their lives. The elder John O'Leary was married a third time, to Margaret Dwyer, with whom he had a son, Edmund (1843–83), later an IRB activist, and a daughter.
John O'Leary was educated at Tipperary grammar school (an Erasmus Smith (qv) foundation) and at Carlow college (1845–7). While convalescing at home in mid 1846 after an attack of typhus he discovered the writings of Thomas Davis (qv), underwent a political conversion experience, and became a reader of the Nation. In 1847 O'Leary enrolled at TCD with the intention of becoming a barrister; however, his legal studies were overshadowed by his activities in the Young Irelanders’ Irish Confederation, where he sided with the radical faction led by John Mitchel (qv). On the outbreak of the 1848 rising O'Leary returned to Tipperary to join the fight, but discovered that the local clubs were almost totally unprepared; he had to go into hiding for a time after attracting the authorities’ attention by chairing a meeting in Tipperary town. The collapse of the rising left O'Leary with an abiding distrust for orators and an abiding belief that, rather than indulging grandiose expectations of victory, rebels should anticipate failure; he decided to abandon the Mitchelite strategy of spontaneous revolt for the plan first articulated by Theobald Wolfe Tone (qv) of preparing an insurrection in advance by means of a secret society.
On 8 November 1848 O'Leary was arrested with a group of Young Ireland sympathisers who had assembled at the ‘Wilderness’ outside Clonmel as part of an unsuccessful plan to free the convicted Young Ireland leaders; he was detained for a few weeks and then released. In 1849 he took part in an abortive revolutionary conspiracy led by James Fintan Lalor (qv), which led to sporadic attempts at a rising in Tipperary and Waterford. He then entered QCC to study medicine (January 1850), but shortly afterwards moved to QCG. This change in career plan was inspired by his discovery that an oath of allegiance was required to practise at the bar. His attendance at the queen's colleges reflected his belief in Young Ireland principles of non-sectarianism, and around this time he ceased to practise catholicism. His first publication was a letter in defence of the queen's colleges published in the Nation on 26 October 1850; Cardinal Cullen (qv) subsequently pointed to O'Leary as proof that the colleges encouraged irreligion and political subversion.
O'Leary was that species of medical student known as a ‘chronic’; financially independent after inheriting property in Tipperary from his father (an inheritance increased by the subsequent deaths of siblings), with no compelling need to practise, he was as much interested in socialising and other activities as in formal studies. He remarked in his memoirs that bookstalls, bookshops, and books generally had taken up such a large proportion of his life that no account of it could be complete without mentioning the fact. After leaving QCG in 1853, he studied surgery in Dublin at the Meath Hospital (1853–4); in 1854–5 he continued his studies and leisure activities in London, and 1855–7 was spent in Paris (where he formed a lifelong friendship with the painter James McNeill Whistler), mingled with the Irish exile community, acquired fluency in French, and became convinced of the merits of constitutional monarchy. In 1857–8 he was back in London, and in 1858–9 continued his increasingly desultory studies in Dublin. There he was recruited by James Stephens (qv) for the latter's new secret society; O'Leary was never sure whether it was originally called the Irish Republican Brotherhood or the Irish Revolutionary Brotherhood, as before 1867 he always heard it referred to as ‘the organisation’. He refused to take the IRB oath on the grounds that it was either unnecessary or superfluous.
O'Leary became the chief financial agent of the new society and was sent to America on a fund-raising mission. Here he was given a large public reception (to his disquiet), travelled around the country on business, and engaged in controversy with T. D. Sullivan (qv) in rival Irish-American newspapers. In September 1859 he returned to Paris, where he had a slight falling-out with Stephens and discovered that his brother Arthur was ill with tuberculosis. They returned to Tipperary, where Arthur died in June 1861. O'Leary spent the next two years leading a mildly bohemian life in London until, in August 1863, Stephens recalled him to act as editor of the new Fenian newspaper, the Irish People, which commenced publication in November 1863. (O'Leary was also best man at Stephens's wedding in January 1864.) Concentrating on the editorial side of the paper, he was proud of its literary merit and, indeed, his own contributions show a distinctive sardonic humour. It was said that O'Leary's editorials could be distinguished by their brevity, irony, and unwillingness to make unqualified assertions.
O'Leary was one of a three-member committee authorised to act for Stephens as IRB leaders in his absence: the others were Thomas Clarke Luby (qv) and Charles Kickham (qv), also leader-writers on the Irish People. The discovery of Stephens's commission constituting this committee played a major role in O'Leary's prosecution for Fenian activities, as did evidence of his continuing role as treasurer. O'Leary was arrested in the early morning of 16 September 1865 during a wider round-up of Fenian activists, which also saw the suppression of the Irish People. He was tried before a special commission on 1–7 December, found guilty of treason-felony, and sentenced to twenty years’ imprisonment. On 23 December he was transferred with other Fenian prisoners to England, and sent to Pentonville prison. On 14 May 1866 he was transferred to Portland prison, where he spent the remainder of his imprisonment in hard labour at the stone quarries and in other menial work, suffering exhaustion and eyestrain. O'Leary believed in general compliance with prison rules on the grounds that this best befitted the dignity of political prisoners – ‘I was in the hands of my enemy; what should I expect?’ – and disapproved of the flamboyant defiance of O'Donovan Rossa (qv). In later life, when discussing similar tactics by William O'Brien (qv) MP, ‘our two months’ martyr’, he added derision to disapproval.
O'Leary received a pardon in January 1871 on condition that he remained outside the UK for the duration of his original sentence, though he was permitted to revisit Ireland on family business in 1878 and 1879. Most Fenian activists released on these conditions went to America, but O'Leary chose to settle in Paris, where he mixed with Irish and other revolutionary exiles, wrote letters to Irish newspapers, and contributed to Irish-American newspapers. He remained in touch with Clan na Gael and the IRB, who regarded him as an elder statesman, and in the late 1870s he resumed his former role as IRB treasurer. Although he disliked the attendance of Irish nationalists at the Westminster parliament, believing that they would inevitably be corrupted, he took some tentative interest in the ‘New Departure’ alliance of agrarian activists, Fenians and militant home-rulers, but broke with the Clan na Gael over its support for the Land League (as did the rump IRB organisation led by Kickham). During the years 1881–3 O'Leary contributed to the Irish Nation founded by John Devoy (qv), but they eventually fell out over O'Leary's attitude to agrarian crime. In 1884 O'Leary publicly condemned the dynamite campaign launched against Britain by Devoy, whom he describes in his memoirs as a Land Leaguer rather than a Fenian. O'Leary had been a long-standing critic of the rival dynamite campaign undertaken by O'Donovan Rossa, though he commented that the British authorities had treated Rossa like an animal in prison and must share the responsibility for his actions.
O'Leary returned to Ireland in January 1885, settled in Rathmines (where his sister Ellen kept house for him), and mingled in literary and political circles. At the Dublin Contemporary Club he met W. B. Yeats (qv), whose genius he recognised; throughout the late 1880s and 1890s he gave the young poet access to his bookshelves, introduced him to the writings of Samuel Ferguson (qv) and to Young Ireland and possibly the IRB, offered criticism of his work (well received) and his occultism (not so well received), and helped place his journalism with Irish and American nationalist periodicals. For Yeats, O'Leary represented a powerful, idiosyncratically honest form of nationalism dissociated from clericalism, rhetoric, and mob politics. Although their friendship lapsed over O'Leary's support for John MacBride (qv) in his marital dispute with Maud Gonne (qv), Yeats memorialised the old Fenian as the embodiment of ‘romantic Ireland’ in his poem ‘September 1913’ and in his autobiographical Reveries over childhood and youth.
On resuming his life in Ireland, O'Leary soon provoked controversy by his opposition to the Plan of Campaign. Although other Fenians such as Kickham shared his view that land reform could only be accomplished by an independent Irish state, O'Leary's house property in Tipperary left him open to criticism when the town became a major focus for agitation against the Smith–Barry estate. The O'Learys had a reputation as harsh landlords and were targeted by the League in 1886. O'Leary was regularly denounced in United Ireland as a self-serving hypocrite. The abandonment of the town by numerous tenants in an unsuccessful attempt to establish a rival ‘New Tipperary’ caused O'Leary considerable financial loss, while Ellen's death in 1889 exacerbated a long-standing tendency to aimlessness, depression, and alcoholism. During the Parnell (qv) ‘split’ O'Leary publicly supported Parnell's leadership, though this did not keep him from criticising Parnellite use of the plight of the New Tipperary tenants as a stick with which to beat John Dillon (qv) and O'Brien; O'Leary pointed out that Parnellites such as Timothy Harrington (qv) were equally responsible for the debacle.
In 1896 O'Leary published Recollections of Fenians and Fenianism, a digressive account of the movement written intermittently over several years, supplemented by the reminiscences of T. C. Luby. The book is noteworthy for its portrayal of Stephens and other Fenian activists, its discussion of the working of the Irish People (towards the end it declines into a commentary on the bound volumes of the newspaper), and for numerous acerbic comments on the adherents of the Land League and home rule. During the 1798 centenary O'Leary chaired the Dublin commemoration committee; he laid the foundation stone for the abortive Wolfe Tone monument at the Grafton Street corner of St Stephen's Green. He also chaired pro-Boer meetings and a committee that opposed the 1900 visit of Queen Victoria to Dublin.
In his last years O'Leary was associated with Arthur Griffith (qv), who regarded him as the elder statesman of Irish nationalism. However, O'Leary criticised some aspects of Griffith's controversial style: he disapproved of Griffith's accusations of bad faith against T. W. Rolleston (qv) for his reversion to unionism, stating that Rolleston was entitled to change his politics even if the change was misguided. O'Leary died (unmarried) in Dublin 16 March 1907 after being reconciled to the catholic church by Father Thomas Finlay (qv) SJ. His career was driven by a stubborn individuality which provoked contemporaries to exasperation and respect.