Gillespie, Sir Robert Rollo (1766–1814), British army general, was born 21 January 1766 in Comber, Co. Down, the only child of Robert Gillespie (d. 1791) and his third wife, who was either the sister or daughter of James Bailie, MP for Hillsborough. He was educated at Norland House, Kensington, and later with a private tutor at Newmarket. It was intended that he would enter Cambridge, but he preferred a military career, and in April 1783 was commissioned as a cornet in the 3rd Irish Horse.
The next few years were steeped in controversy and it seemed likely that his career would end in ruins. In November 1786 he secretly married Annabell, daughter of Thomas Taylor of Taylor's Grange, Co. Dublin. He had met her only a few weeks previously. In December 1787 he acted as second to Lt McKenzie in a duel with William Barrington, brother of Sir Jonah Barrington (qv). When both principals had discharged their pistols without effect, a quarrel developed between Gillespie and Barrington. Shots were duly exchanged and Barrington was killed. Gillespie initially fled to Scotland but later returned and surrendered himself for trial. The case was tried at the assizes in Maryborough, Queen's Co. (Laois), in March 1788 and, despite the recommendations of the judge, the jury returned a verdict of justifiable homicide.
Promotion to the rank of lieutenant in the 20th Jamaica Light Dragoons in 1792 offered Gillespie the chance to leave Ireland and distinguish himself in the West Indies. During his voyage there he survived a shipwreck at Madeira, and then contracted yellow fever on his arrival. In 1794 he was promoted to captain, was present at the battle of Tiburón on the west coast of Colombia, and later took part in the captures of Fort Bizotten and Port-au-Prince, being wounded several times during this campaign. Promoted to major (1796), he was appointed brigade-major to Gen. Wilford in San Domingo and later served as adjutant-general. He came to be known and feared by insurgent groups on the island and on one occasion was the target of an assassination attempt, reputedly killing six of his attackers before being shot and wounded himself. In 1799 he was promoted to lieutenant-colonel and given command of the 20th Light Dragoons.
After the peace of Amiens he returned to England with his regiment but was soon embroiled in another controversy. Accused of signing false returns, he was tried by general court martial in June 1804 and acquitted. Due to financial difficulties, however, he was forced to exchange into a regiment stationed in India. He travelled across Europe and, while in Hamburg, was warned by James Napper Tandy (qv) of a French plot to capture him. Gillespie continued his journey in disguise to avoid the attentions of the French, following a circuitous route and visiting Vienna, Greece, Aleppo, and Baghdad.
On arriving in India he was appointed commander at Arcot, and on 10 July 1806 was informed of a mutiny among Indian troops at Vellore. He set out immediately for Vellore with a troop of the 19th Light Dragoons and arrived on the scene just as the European troops stationed there were running out of ammunition. He rallied the defence and held out till the arrival of reinforcements and artillery. In the months that followed he subdued further outbreaks of discontent among other Indian regiments. In 1807 he took over command of the King's Royal Irish Light Dragoons and, during the campaign against Runjit Singh in 1809, he commanded both the cavalry and horse artillery.
Promoted to brigadier-general, he led the advance guard during the Java war of 1811–12, serving under Gen. Sir Samuel Auchmuty. He commanded the land invasion force that landed at Chillingcherry and forced the surrender of Batavia, and was present at the siege of Cornelis, surviving a second assassination attempt when he and his staff were served poisoned coffee. On 26 August 1811 he led the final assault on the Dutch defences at Cornelis, capturing the town. In the aftermath of the war he was appointed military governor of Java, cooperating with the civil governor, Stamford Raffles. In March 1812 he led a force to Sumatra after a massacre of Europeans by the troops led by the pro-Dutch sultan of Palembang. He deposed the sultan and also secured the island of Banca. On his return to Java he found that a coalition of Javanese chiefs had assembled an army of over 30,000 men at a strongly fortified position at Jogjakarta (Jakarta), which he stormed with just 1,500 men. His relationship with Raffles deteriorated, however, and he levelled a number of charges against him, questioning his administration of the island and his practice of selling tracts of land. The East India Company followed up Gillespie's accusations and after a long inquiry found against Raffles in 1814.
In April 1812 Gillespie was promoted to major-general and, resigning his command in Java, he returned to India, where he took command at Meerut. By this time he enjoyed a level of celebrity and his popularity increased further when he shot a tiger on the racetrack at Bangalore during a race meeting. At the outbreak of the Nepal war in 1814 he was appointed to command the Meerut division of the Bengal army. In October 1814 he began to prepare for an assault on the Gurkha fort at Kalunga near Dehra Dun (Dera Dun). This was a well fortified strongpoint perched on a hilltop in the Siwalik foothills of the Himalayas. Gillespie personally led the main assault on the fort on 31 October and tried to rally his troops when the attack stalled after a Gurkha sortie. Turning to a young Irish lieutenant from Cultra, he called out: ‘Now Kennedy, for the honour of County Down’ (Murray, i, 371) but was shot through the heart as the attack resumed. His remains were returned to Meerut for burial. News of his death did not reach England for several months and he was included in the new year's honours list in 1815, being created a KCB. While his early career had been unpromising, a series of military successes, combined with his reputation for fearlessness, had elevated him to an almost iconic status, and for the remainder of the nineteenth century he was held up as an example to young officers serving in India.
There is a monument to Gillespie in St Paul's cathedral, London. Commemorative obelisks were erected in Calcutta cathedral and in Meerut cemetery. There is also a monument in the market square in Comber, Co. Down.