Boland, Henry James (‘Harry’) (1887–1922), revolutionary, was born 27 April 1887 at 6 Dalymount Terrace, Phibsborough Rd, north Dublin, third of five children of James Boland (qv), paving foreman and eventually overseer for Dublin corporation, and Catherine (‘Kate’) Boland (née Woods; c.1861–1932). James Boland was a dedicated Fenian and GAA official, and his death from a brain cyst in 1895, when only 38, was ascribed to a battle with anti-Parnellites in December 1890 for possession of the office of United Ireland. The manner of his father's life and death were critical influences on Harry's development as a revolutionary. The family was shielded from destitution by public subscriptions raised after the funeral, a massive gathering of Parnellites, conspirators, and sportsmen. Kate was able to secure a south-side tobacconist's shop in Wexford St., before moving to nearby Lennox St. in 1907, and north to 15 Marino Crescent (the Clontarf birthplace of Bram Stoker (qv)) in 1914. After a turbulent period with the Christian Brothers at Synge St., Harry was accepted in about 1902 as a boarder by the De La Salle Brothers at Castletown, Queen's Co. (Laois), with the prospect of a noviciate. Lacking both money and a vocation, he soon left school and worked briefly in Manchester before becoming a tailor's cutter in Todd, Burns, & Co. of Mary St., then one of Dublin's largest department stores. He emulated his father by joining the IRB and GAA, as well as the radical Keating branch of the Gaelic League. His Irish remained rudimentary, but his hurling was proficient enough to earn him a place on the Dublin team for the All-Ireland senior final in 1909. He proved even more adept as a sporting administrator, securing his father's former post as Dublin county chairman in 1911. By November 1913, when he became a founding member of the Irish Volunteers, Boland was already an influential ‘insider’ in Dublin's republican underground. He supported the Volunteers’ provisional committee when it repudiated the leadership of John Redmond (qv) in October 1914, and continued to drill with F Company, 2nd Battalion, Dublin Brigade. Known to the public only as a hurler, he was an activist but not a leader until the rebellion of 1916. In these respects, as in many others, he resembled Michael Collins (qv), whom he is said to have introduced to the IRB when visiting London in 1909.
In 1916 Harry Boland was still living with his mother and his surviving sister Kathleen (1889–1954) in Marino Crescent, his brothers Gerald (1885–1973) and Edmund (1893–1928) having left home. All three brothers were involved in the rebellion, Edmund avoiding arrest after the surrender of Pearse (qv), and Gerald being interned along with Michael Collins, whom he disliked and distrusted. After some initial sorties around Fairview, Harry entered the GPO on Easter Tuesday evening, being one of the last to escape the bombardment three days later, after gallantly disabling unused bombs in the basement. Though neither an officer nor a noteworthy combatant in the rebellion, he was court-martialled and sentenced to ten years’ penal servitude, having been pointed out by a musketry instructor whom he had incarcerated in the GPO. This fortuitous promotion from the ranks gave Boland the opportunity to demonstrate his finesse as an organiser to emerging leaders such as Eamon de Valera (qv), his fellow-prisoner at Dartmoor, Lewes, and Maidstone. With his hearty good humour, robust self-confidence, and ingenuity in devising torments for the warders, he was quickly identified as a ringleader by the authorities and a likely leader by republicans.
Following the general amnesty of June 1917, Boland rapidly reasserted his influence in the republican fraternities, while using the cachet of the freedom fighter to infatuate a procession of women. Though one found him ‘a bluff hearty fellow’ who was ‘a wee bit rough’ (quoted in Fitzpatrick, 90), others such as Kitty Kiernan (qv) of Granard, Co. Longford, were entranced by his fashionable attire, boisterous antics, fervent singing, and dramatic stories. His chief partner in both republican and sexual politics was Collins, who usually excelled Boland in both pursuits and thus gained an ascendancy that turned sour only in 1921. Both were elected to the executive of Sinn Féin when it was reconstituted in October 1917, so promoting IRB influence over that vast and unwieldy popular movement. Whereas Collins antagonised the ‘politicians’ and soon redirected his energy to the Volunteers, Boland became a key figure in drafting propaganda, organising electoral campaigns, and maintaining morale at headquarters in 6 Harcourt St. After the arrest of de Valera and most other leading republicans in May 1918, those shrewd enough to evade arrest consolidated their power. While Collins and Richard Mulcahy (qv) prepared the Volunteers for armed resistance against conscription, Boland became joint honorary secretary of Sinn Féin and an architect of its electoral triumph after the armistice. Mildly socialist by inclination, and egalitarian in manner, he managed to win the confidence of Labour leaders and manoeuvre them into withdrawing from the election and collaborating with Dáil Éireann, the republican assembly inaugurated in January 1919. Boland secured election for Roscommon South, outpolling by 10,685 votes to 4,233 his ‘constitutionalist’ opponent who had mocked him as ‘only a tramp tailor’ (quoted in Fitzpatrick, 110).
Boland's growing political influence was still underpinned by his fraternal and conspiratorial connections. He remained active in administering and politicising the GAA, which repaid his investment in November 1917 by organising a benefit hurling match at Croke Park, so helping Boland to set up his own tailoring business at 64 Middle Abbey St. The arrest of Seán McGarry (qv) in May 1918 allowed Boland to join the IRB's supreme council, of which he was soon elected president (and therefore, according to its then constitution, president of the republic). Its treasurer was Collins, with whom Boland continued to consort, wrestle, hurl, and tipple while ‘on the run’. They collaborated in the spectacular rescue of de Valera from Lincoln gaol in February 1919, a bloodless triumph of ingenuity and improvisation. Three months later, bearing informal ‘credentials’ from de Valera and Collins, Boland was sent to the USA as an ‘envoy’ (his official designation) of both the dáil and the supreme council.
Boland's mission was conducted on many levels, illuminating the shadowy connections between the administrative, political, military, and conspiratorial strands of the Irish revolution. Throughout de Valera's own period in America (June 1919–December 1920), Boland acted as his private secretary, tour organiser, bagman, political adviser, butler, and personal entertainer. With difficulty, he managed to offload responsibility for the promotion and sale of republican ‘bonds’, which presented daunting managerial and technical problems beyond his competence. Charged with restoring unity among the squabbling factions of Irish-American activists, he ultimately did more than most to foster disunity. After impassioned, sustained, but futile attempts to reconcile the Friends of Irish Freedom and Clan na Gael to de Valera's Irish-centred political strategy, Boland disavowed both organisations in late 1920, organising rival bodies under his own dictatorial management. The creation of a tame American Association for the Recognition of the Irish Republic was widely publicised; but the ‘reorganisation’ of Clan na Gael, as a subsidiary body to the ‘Home Organisation’, was a clandestine undertaking that horrified the IRB and exasperated even Collins. Boland's ruthless campaign against John Devoy (qv) and Daniel Cohalan (qv) alienated many old supporters of the ‘Irish cause’ in America; but his team of organisers and propagandists mobilised hundreds of thousands of Americans, many without Irish antecedents, behind the demand for self-determination. The strategy of confrontation was de Valera's, but Boland was largely responsible for its execution.
Still deeper motives lay behind Boland's presence in America through most of the Irish revolution. He coordinated an ambitious programme for procuring arms and smuggling them to Ireland, which required him to recruit and manipulate an intricate network of agents and contacts. Though ostensibly subject to the authority of Cathal Brugha (qv) as minister for defence, these operations were conducted through the IRB and its American affiliates, leading to bitter conflict between Brugha and Boland over funding and supervision. Boland's reputation as a master gun-runner was shattered, in June 1921, by the capture in Hoboken of 495 Thompson sub-machine guns. Boland made his second trip home in August 1921 to attend the second dáil (to which he had been elected unopposed) and also to vindicate his conduct, returning to America with enhanced ‘diplomatic’ credentials. In addition to securing weapons capable of transforming the Irish Volunteers into an army, he had the still more startling ambition of building up a worldwide network of conspirators ready to attack ‘British’ targets overseas. This scheme, concocted with Collins in 1919 but still in gestation in 1921, was suspended during the truce and never tested.
Before returning to America, Boland had resumed his role as de Valera's faithful messenger, acting as an intermediary with Lloyd George at Gairloch in September 1921. His eventual decision to follow ‘the Chief’ in opposing the treaty settlement, though presented as an independent expression of political principle, was influenced both by loyalty to de Valera and growing animosity towards Collins. In Boland's absence, Collins had taken charge not only of the IRB but of Kitty Kiernan, who had been intermittently pursued by both men since 1917. Boland reached Dublin on 5 January 1922, in time to vote with the minority of deputies against the treaty. More strongly than Collins, he continued to believe that fraternal solidarity could surmount all divisions, and spent the first half of 1922 seeking a reconciliation between Collins and de Valera. Ever optimistic and cheerful, he imagined that goodwill and belief in the cause of freedom could prevail against sectional and personal animosities. He was a key figure in negotiating the abortive ‘pact’ preceding the election of June 1922, in which he was again elected without opposition to the dáil.
At the outbreak of civil war (28 June 1922), for the first time since the rebellion, he took arms against the government (as did his brothers). Briefly quartermaster-general for the IRA's Eastern Command, in July he was prominent in the occupation and abandonment of Blessington, Co. Wicklow. After a period on the run in Dublin, and the capture of his letter soliciting money and guns from Clan na Gael, Boland was surprised on 31 July by a raiding party in the Grand Hotel, Skerries, Co. Dublin, and was shot and seriously wounded. He died 1 August 1922 in St Vincent's Hospital, Dublin. His personal estate amounted to only £657 in cash and insurance policies, his tailoring business having collapsed during his absence in America. The most important collections of papers relating to him are in de Valera's papers (UCD Archives) and in family possession.
Harry Boland's funeral procession to Glasnevin attracted vast crowds to mourn one of the most genial, attractive, yet impenetrable of Irish revolutionaries. The event was recorded by Jack Yeats (qv) in two striking paintings (‘A funeral’ (1922), Niland Gallery, Sligo; ‘A lament’ (1930), private owner) which convey the general dismay occasioned by his loss. Loyal and sincere, intimate with the leaders of both factions, he epitomised in his death the failure of the revolutionary ideal.