His extracurricular interests, which also included cycling and drinking, prevented him from being an attentive student, and in 1898 he switched to the medical school at Trinity College, having failed eight of his ten examinations at the Royal.
His witty conversation made him a favourite with the dons, particularly John Pentland Mahaffy (formerly the tutor of Oscar Wilde) and Robert Yelverton Tyrrell, and between 1901 and 1903 he won three successive Vice-Chancellor's prizes for verse.
Joyce briefly took up residence in the Tower the following month, together with Gogarty and his Oxford friend Samuel Chenevix Trench (a setup which later provided inspiration for the opening chapter of Ulysses) but left again after only six days.
[17] In 1905 Gogarty became one of the founding members of Arthur Griffith's Sinn Féin, a non-violent political movement with a plan for Irish autonomy modelled after the Austro-Hungarian dual monarchy.
Returning to Dublin in 1908, Gogarty secured a post at Richmond Hospital, and shortly afterwards purchased a house in Ely Place opposite George Moore.
[22] As a Sinn Féiner during the Irish War of Independence, Gogarty participated in a variety of anti-Black and Tan schemes, allowing his home to be used as a safe house and transporting disguised IRA volunteers in his car.
[23] Following the ratification of the Anglo-Irish Treaty, Gogarty sided with the pro-Treaty government (headed by his close friend Arthur Griffith) and was made a Free State Senator.
[27] In November 1922, anti-Treaty IRA commander Liam Lynch issued a general order to his forces to shoot Free State senators.
Two months later, Gogarty was kidnapped by a group of anti-Treaty militants, who lured him out of his house and into a waiting car under the pretext of bringing him to visit a sick patient.
Aware that he might be in imminent danger of execution, Gogarty contrived to have himself led out into the garden (purportedly by claiming to be suffering from diarrhoea), where he broke free from his captors and flung himself into the River Liffey; he then swam to shore and delivered himself to the protection of the police barracks in Phoenix Park.
De Valera eventually dissolved the Seanad when it persisted in obstructing Government proposals, effectively ending Gogarty's political career.
[32] Gogarty maintained close friendships with W. B. Yeats, AE, George Moore, Lord Dunsany, James Stephens, Seamus O'Sullivan, and other Dublin literati, and he continued to write poetry in the midst of his political and professional duties.
1936 saw the publication of Yeats's Oxford Book of Modern Verse, which contained seventeen of Gogarty's poems and an introduction proclaiming him "one of the great lyric poets of our age.
The two men did not appear as named characters in the book, but some derogatory lines of verse beginning "Two Jews grew in Sackville Street", written by Gogarty's friend George Redding and included in a scene in the novel, were widely known to refer to the Sinclair siblings.
[40] The case attracted a great deal of public attention, with one commentator observing that "only The Pickwick Papers, rewritten by James Joyce, could really capture the mood of this trial.
"[41] Among the witnesses for the plaintiff was William Sinclair's nephew-by-marriage, Samuel Beckett, then a little-known writer, who was humiliatingly denounced as a "bawd and blasphemer" by Gogarty's counsel.
This outcome deeply embittered Gogarty, who had already suffered financial setbacks after the stock market crash of 1929[43] and felt that the verdict had been politically motivated.
[45] With the onset of World War II, Gogarty, who was an enthusiastic and talented amateur aviator, attempted to enlist in the RAF and the RAMC as a doctor.
When his return to Ireland was delayed by the war, Gogarty applied for American citizenship and eventually decided to reside permanently in the United States.
Though he regularly sent letters, funds, and care packages to his family and returned home for occasional holiday visits, he never again lived in Ireland for any extended length of time.
In addition to various essays and short stories, his prose output included Going Native, a satire on English social mores, Mad Grandeur and Mr. Petunia, two period narratives composed with an eye to having them optioned as Hollywood films, and Rolling Down the Lea and It Isn't This Time of Year at All!, two loosely constructed memoirs.
A highly visible and distinctive Dublin character during his lifetime, Gogarty appears in a number of memoirs penned by his contemporaries, notably George Moore's Hail and Farewell, where he goes both by his own name and by the pseudonym "Conan".
[52] A pub in the Temple Bar district of Dublin is named after him, and an annual Oliver St. John Gogarty Literary Festival is held in the author's family home, now the Renvyle House Hotel in Connemara.