In 1893, at the age of 15, he wrote a letter to his local newspaper in County Down stating that "Gaelic" was irretrievably dead and "the study of Esperanto would be more useful to the youth of Ireland".

Although Joyce and Skeffington disagreed with each other's politics, they both resented censorship, and agreed to co-finance the print run of 85 copies and distribute the pamphlet to newspapers and prominent Dubliners.

[19] After graduating from University College, Skeffington worked as a freelance journalist, contributing to socialist and pacifist publications in Ireland, England, France and North America.

To open the meeting, the president of the chamber proposed that "a Citizens' Committee be formed for the purpose of arranging a suitable welcome and preparing and presenting a loyal address to the Most Gracious Majesties the King and Queen, on their approaching visit to Dublin".

"Sean Milroy – a future minister in the Irish Free State – stood to second Sheehy Skeffington's motion, while the chairman, the Earl of Mayo, attempted to maintain order over cries of 'Hear hear!'

[27] During the 1913 Dublin Lock-out, he became involved in the Citizens' Peace Committee, a group formed by various people including Tom Kettle and Thomas MacDonagh, with Joseph Plunkett as secretary, whose goal was to reconcile the employers and workers.

[citation needed] Sheehy Skeffington testified before a tribunal in 1913 as a witness to the arrest of the leading trade unionist Jim Larkin on O'Connell Street, and the subsequent police assault against a peaceful crowd, which had occurred on the last weekend of August 1913.

He said that he was later abused by a gang of policemen showing clear signs of intoxication in the yard of the police station at College Green where he went to make his complaint, and that their officers had no control over their behaviour.

[29] He supported the peace crusade of the American car manufacturer Henry Ford; and when Countess Markievicz advocated armed uprising by Irish nationalists, he challenged her to a debate on the subject.

[32] But Sheehy Skeffington's death can be more accurately explained as the unlucky consequence of Dublin Castle's suspicion that he was a Sinn Fein conspirator[33][34] and Captain John Bowen-Colthurst's violent hostility towards suspected rebel sympathisers.

"[38] Shortly after that incident Sheehy Skeffington was seen climbing up onto the steps of Nelson's Pillar on Sackville Street and calling upon a group of inner-city paupers to stop looting shops.

[42] Captain John Colthurst Bowen-Colthurst (1880–1965) was an officer of the reserve 3rd Battalion of Royal Irish Rifles and he belonged to an old Anglo-Irish and Protestant Ascendancy family with an extensive estate in County Cork.

[43] At the start of World War I, he spent five weeks with the British Expeditionary Force on the Western Front (14 August – 19 September 1914), from which he had been sent home wounded and possibly shell-shocked.

About 10:30 p.m. on the second day of the Rising (25 April),[47] Captain Bowen-Colthurst took Sheehy Skeffington out of the barracks, as a hostage for a raiding party on the tobacconist shop of Alderman James Kelly, a moderate 'home rule' nationalist.

)[42][48] The raiding party consisted of an officer (Lieutenant Leslie Wilson) and 40 men led by Bowen-Colthurst, along with Sheehy Skeffington who had his hands tied behind his back.

[49] The troops left the barracks and headed towards Rathmines Road, where they encountered three young people loitering opposite the Church of Mary Immaculate, Refuge of Sinners.

[53] The party continued down the Lower Rathmines Road, and the soldiers stopped at the Portobello Bridge, where half of the men were left at a guardhouse along with Sheehy Skeffington.

Months later, when Countess Markievicz – then in Mountjoy Prison — first heard of the executions of the leaders of the Easter Rising, she expressed surprise at only one thing: "Why on earth did they shoot Skeffy?"

The guard room was not safe for these desperate men to be confined in, their rescue from outside would be very easy.On Tuesday and up to Wednesday morning rumours of massacres of police and soldiers from all parts of Dublin were being constantly sent to me from different sources...

Father Scannell alleged that Bowen-Colthurst detained several bricklayers from a nearby building site, and ordered them to repair the broken and bullet-impacted bricks in the wall behind where the executed men had stood.

[40][42] On that same Friday evening, Bowen-Colthurst and a group of soldiers forced entry into the Sheehy Skeffingtons' home, hoping to find evidence to incriminate Francis as an enemy sympathiser.

[42] According to an official report, "All the rooms in the house were thoroughly ransacked and a considerable quantity of books and papers were wrapped up in the household linen, placed in a passing motor car, and taken away. ...

[76] Once the prosecution and defence counsel had established the uncontested facts of the case, a succession of army officers testified to Bowen-Colthurst's kindness and decency but also to his occasional eccentricity, excitability and impulsiveness.

[86] The prosecutor noted that the onus of proof for an insanity defence lay on the accused, but that there was no evidence Bowen-Colthurst had not been able to distinguish right from wrong, and that he knew what he was doing when he ordered the men to be shot.

At the request of defence counsel, the Adjutant read into the record that Captain Colthurst and his machine-gun detachment were mentioned in dispatches during the Tibet Expedition, and the proceedings concluded.

Important witnesses (Colonel McCammond, Lieutenants Tooley and Gibbon, Sergeant Claxton and others), who might have provided different views of Bowen-Colthurst's character and mental state, were not summoned to give evidence.

[95] The Royal Commission on the Arrest... and subsequent treatment... of Sheehy Skeffington... Dickson and...McIntyre was chaired by Sir John Simon (a former Attorney General and Home Secretary), and held hearings on 23–31 August 1916 in a public courtroom at the Four Courts in Dublin.

[100] Wilson also told the commission panel that he thought it was quite legal to use Sheehy Skeffington as a hostage and did not consider the instruction to shoot him if Colthurst's party was fired on as 'strange'.

It operates solely as a warning that the Government, acting through the military, is about to take such forcible and exceptional measures as may be necessary for the purpose of putting down insurrection and restoring order....

We should have deemed it superfluous to point this out were it not that the failure to realise and apply this elementary principle seems to explain the free hand which Captain Bowen-Colthurst was not restrained from exercising throughout the period of crisis.