Gregory, (William) Robert (1881–1918), painter, theatre designer, sportsman, and airman, was born 20 May 1881 in London, only child of Sir William Gregory (qv) of Coole Park, Co. Galway, and his second wife, Isabella Augusta (née Persse), Lady Gregory (qv), writer, dramatist, and patron of the arts. Sir William's advanced age at the time of his son's birth gave rise to rumours in Gort that Robert was actually fathered by a local blacksmith called Seanín Farrell in a collusive arrangement to provide the estate with a direct heir; this is considered unlikely, since Robert's conception took place soon after his parents’ marriage. His birth involved the estate in financial complications, since the collateral heir, Sir William's cousin Charles Gregory, held a large mortgage on the estate, lent on the assumption that his eventual inheritance would obviate any need for repayment. Much of Robert's early childhood was spent among his Persse relatives in Co. Galway, both in accordance with contemporary aristocratic child-rearing practices and because Sir William expected his wife to place him first and accompany him in high society and journeyings. Augusta, who experienced some discomfort at this, developed a strong affection for Robert, and after Sir William's death (1892) combined her intellectual pursuits with financial stringency in order to preserve the estate for Robert and his descendants.
Robert was educated at a London day school, then at Park Hill boarding school, Lyndhurst, Sussex, Elstree school, north of London, and Harrow, before entering New College, Oxford (1899–1903). He spent his summers at Coole, amusing himself and being introduced to his tenants. At school and university he was talented but lazy. His principal interests were in sport. He boxed at school, later represented his Oxford college, and also participated in the French amateur championships. As a teenager he formed a cricket team among estate tenants and employees; he was an accomplished fast bowler who played for Phoenix Cricket Club, Dublin, and took eight wickets in a Scotland v. Ireland match (1912). He came to share some of his mother's cultural interests (though remaining a staunch unionist and imperialist), but a short-lived attempt to learn Irish in 1897 did not outlast the advent of the shooting season. He once claimed that in a dream he had been offered the ability to see visions but turned it down in case it disrupted his cricket-playing. As a child Gregory allegedly showed an interest in hurling, extinguished on class grounds. He possessed the small build required for a good jockey; hunting with the Galway Blazers and jumping at Gort show, he carried out feats of horsemanship that became legendary.
As an undergraduate Gregory began to design for the Abbey Theatre, in 1903, producing effective settings (deploying curtains of different colours) for ‘Twenty-five’ by his mother and costumes for ‘The hour glass’ (1903) by W. B. Yeats (qv). From 1905 he was involved in major projects at the Abbey Theatre, designing sets and costumes for Lady Gregory's ‘Kincora’ (1905), and scenery for the Deirdre plays of Yeats and J. M. Synge (qv), Yeats's ‘On Baile's strand’ and ‘The shadowy waters’, and ‘The nativity’ (1911) by Douglas Hyde (qv). Yeats (himself fiercely disciplined in his artistic life) found Gregory dilatory and replaced him by the more advanced Gordon Craig. He also contributed illustrations to the Dun Emer Press at the behest of Yeats (who subsidised it), despite protests from Elizabeth Corbet Yeats (qv) that ‘I don't want Robert Gregory's masterpieces’ (Foster, Apprentice mage, 351).
Deciding to pursue an artistic career, Gregory attended (1903–5) the Slade School of Fine Art, London, where he studied under Henry Tonks, was influenced by Augustus John, and made the acquaintance of Margaret Parry, whom he married (26 September 1906); they had a son and two daughters. Robert and Margaret spent much of their time in Paris, where he undertook further study under J. E. Blanche; their children were left with their grandmother at Coole in a manner resembling Robert's own early upbringing. He provided four illustrations for Lady Gregory's Kiltartan history book (1909) and showed some talent as a painter (in simplified post-impressionist style) of south Galway and north Clare landscapes. He held two major London exhibitions at the Baillie Gallery (1912) and the Chenil Gallery (1914).
Robert showed little interest in estate management, leaving this (and the difficult negotiations surrounding the sale of the Coole estate to the tenants in the years before the first world war) to his mother. He was nonetheless absolute owner of the estate, a situation which Augusta reinforced by allowing him to break the entail after he came of age; in so doing she unintentionally deprived herself of the legal right to remain tenant for life, assigned to her under Sir William's will. She remained confident in her moral rights (she had spent much of her own money on the estate, even buying some additional land during Robert's minority, transferred significant shareholdings to her son and daughter-in-law on their marriage, and placed much of her literary income in trust for her grandchildren) but despite personal affection tensions grew up between her and the young couple. These centred on Yeats's presence at Coole (he usually spent between two and three months a year there), the fact that when in residence he was treated as master of the house, and Yeats's tactfully concealed view that Gregory, though possessing considerable talent, was dilettantish and lacked direction. Just before the outbreak of the first world war the resulting strain led Yeats to cut down on his time at Coole, leading him to spend more time in England and establish the contact with Ezra Pound which produced a major reworking of his style.
Eleven of Gregory's maternal cousins fought in the first world war; six were killed. His enlistment was delayed by the need to complete the procedures for the sale of the Coole estate. After an unsuccessful attempt by his mother to have him appointed director of the NGI in succession to Hugh Lane (qv), he joined 4th Bn, Connaught Rangers, as a second lieutenant in September 1915, transferring shortly afterwards to the RFC, for which his small stature fitted him. He proved to be an excellent pilot, initially flying coastal patrols off Dover. Attached to 40 Sqn, he flew as a scout above the Somme and Ypres fronts (July 1916–November 1917). On 25 September 1916, while escorting a bombing raid, he was shot down by anti-aircraft fire; his FE8 aircraft was totally wrecked, but he escaped unhurt. He was promoted flight commander in January 1917 and squadron commander shortly thereafter, receiving the French Légion d'honneur in June and the MC in July. He told George Bernard Shaw (qv) that his combat experience had been the most satisfactory period of his life because of its intensity. In November 1917, one of the most experienced pilots in the RFC, with nineteen confirmed kills, he transferred to the Italian front as a training officer and commanded 66 Sqn. He was killed 23 January 1918, probably shot down in error by an Italian pilot (his family were told he fainted at the controls because of an adverse reaction to a recent immunisation). He is buried at Padua main cemetery.
Prompted by Augusta, Yeats wrote a tribute to Gregory in the Observer (February 1918) and later eulogised him in four poems. The pastoral ‘Shepherd and goatherd’ was followed by ‘In memory of Major Robert Gregory’ (in which what Yeats had previously regarded as dilettantism is presented as aristocratic sprezzatura and the all-round excellence of a renaissance man). Gregory is chiefly remembered because of the third poem, ‘An Irish airman foresees his death’ in which Gregory's political commitment to empire is conjured away and his military service ascribed to existential self-assertion. ‘Reprisals’, written in 1920, bitterly invites Gregory's spirit to return to Gort and witness the Black and Tans terrorising his former tenants in the name of the cause which he supposedly served, before returning to ‘all the other cheated dead’. Augusta thought this ‘not a very sincere poem’ because Yeats had not witnessed the reprisals first-hand as she had; because of her protest at ‘dragging Robert from his grave’ (Kohfeldt, 267–8) the poem was withdrawn from publication until after Yeats's death. Gregory was also commemorated on a roll of honour in the Church of Ireland church at Gort, Co. Galway, latterly a local library.
In a will written on his way to the front after a period of leave, Gregory left all he possessed to his wife, who was given absolute discretion in managing the estate. His decision, which has been attributed both to an emotional reaction at parting from Margaret (who was pregnant in the last months of his life and miscarried a month before his death) and to long-standing resentment of his mother's authority, led to renewed tensions between Augusta (who wanted the house preserved for Robert's son) and Margaret (who believed there was no future for her children at Coole, a view reinforced after she survived an IRA ambush in which friends were killed). The house was sold in 1927; Augusta remained as a tenant, but her last months were marred by painful squabbles with Margaret (who remarried in 1928) over the furnishings.
As he had many artistic friends, there are numerous portraits of Gregory, including one of him as a youth by John B. Yeats (qv) and another of him in RFC uniform by George Beresford. Three of Gregory's own paintings are held by the NGI, while another sketch is in the possession of the Berg collection of the New York Public Library. His portrait of the actor Arthur Sinclair (1883–1951), in costume as James II (qv), hangs in the Abbey Theatre.