In early 1787 the 3rd Regiment of Horse, a cavalry regiment, arrived at the Barracks in Athy. They had been stationed for the preceding year in Clogher, Co. Tyrone. Amongst their number was a young officer, Robert Rollo Gillespie. A native of Comber, Co. Down, he had joined the regiment in 1783 very much against his family’s wishes who had anticipated that he would become a lawyer, but he was a man of adventurous spirit and the military life was one that appealed to him most. During his time in Clogher he made the acquaintance of a Miss Annabel Taylor, the daughter of the Anglican Dean of Clogher. Having only met in June of 1786 Gillespie and Annabel eloped to Dublin on 24th November 1786 where they were married without the knowledge of either’s family. Notwithstanding the suddenness of their marriage, the union was welcomed by both families and they returned to Clogher after a short time at Ravensdale, an estate owned by Annabel’s brother in Dublin. Among their acquaintances at Clogher, and a friend of Annabel’s family, was William Barrington a landowner from Laois whose brother Jonah Barrington would be M.P. for Clogher in 1798.
While they were not long in Athy, living in married quarters in the Barracks, they held a soiree one evening inviting their friend William Barrington and a fellow officer of Gillespie's, Lieutenant McKenzie. An argument, fuelled by alcohol, broke out between Lieutenant McKenzie and William Barrington, resulting in Barrington challenging McKenzie to a duel the next morning. Despite the intercession of friends present nothing would dissuade the two from the duel. Certain sources suggest that Barrington insisted that the duel be held on land belonging to his family in Laois, which appears to have been somewhere half way between Athy and Carlow, but the exact location is not now known. The next morning both parties appeared at the appointed hour attended by friends. After an exchange of shots neither suffered any injury. Accounts differ as to what happened next. An early memoir of Gillespie suggests that it was proposed that both parties should deem themselves satisfied with the result of the duel shake hands and let the matter be forgotten. This is something that Jonah Barrington had done at a duel in 1759 and appeared to be a common enough occurrence where both parties had escaped serious injury. This unfortunately did not occur on this occasion. Other sources suggest that Barrington, enraged by his failure to wound or kill McKenzie, began a heated argument with Gillespie, while other accounts state that Gillespie was the aggressor in the argument. In any event a second duel was immediately arranged at handkerchief length, and a single shot from Gillespie’s pistol mortally wounded Barrington. The memoir of Gillespie’s life published in 1816 suggests that Gillespie sought the forgiveness of Barrington for mortally wounding him, while Jonah Barrington’s own memoirs Personal Sketches of his Own Times suggest that the shooting of his brother was nothing short of murder by Gillespie. Barrington was not present at the duel and his account is coloured by the loss of his brother. He described Gillespie as 'a dangerous man – an impetuous, unsafe companion – capable of anything in his anger'. Gillespie fled to Athy, then Dublin with his wife, and thereafter to Scotland. Ironically Jonah Barrington would flee Ireland in 1815 to escape his creditors and would end his days in Versaille.
After a number of months in Scotland, Gillespie returned to Ireland and making arrangements in Dublin surrendered himself at Maryborough (now Portlaoise) where he was committed to prison in the town. At the summer assizes of 1788 and despite a summing up by Judge Bradstreet very much prejudicial to Gillespie, the jury, which included a number of army officers, brought in a verdict of 'justifiable homicide'.
Gillespie’s life thereafter was to be one of adventure. After the death of his father in 1791 he went abroad on active service with the British Army. He was shipwrecked near Madeira on his way out to Jamaica. He fought wars in the West Indies, India, Java, Sumatra, rising to the rank of Brigadier General and while leading his troops on the 31st of October 1814 attacking the frontier defences of the fort at Kalunga in Java, he was shot through the heart.
His body was brought to Meerut in India for internment and an obelisk was erected to his memory. A public monument was erected in St. Paul’s Cathedral in London in 1820 and his home town of Comber commemorated him with the erection of a statue to his memory on 4th June 1845. The monument, a 55 feet high column surmounted with a figure of Rollo Gillespie dominates Comber's main square to this day.