Early Life and The First World War
O'Connor was born in Srinagar, Kashmir, India, on 21 August 1889. His father was a major in the Royal Irish Fusiliers, and his mother was the daughter of a former Governor of India's central provinces. He attended Tonbridge Castle School in 1899 and The Towers School in Crowthorne in 1902. In 1903, after his father's death in an accident, he transferred to Wellington School in Somerset. He attended the Royal Military Academy Sandhurst in 1908. In September of the following year he was commissioned, and posted to the 2nd Battalion of the Cameronians. He would maintain close ties with the unit for the rest of his life. In January 1910, the battalion was rotated to Colchester, where he received signals and rifle training. It was then stationed in Malta from 1911 to 1912 where O'Connor served as Regimental Signals Officer.
During World War I, O'Connor served as Signals Officer of 22 Brigade in the 7th Division and captain in command of 7th Division's Signals Company. From October 1916, as a captain and later as a brevet major, he served as brigade major of 91 Brigade, 7th Division. He was awarded the Military Cross in February 1915. In March of that year he saw action at Arras and Bullecourt. O'Connor was awarded the DSO and appointed brevet lieutenant-colonel in command of 2nd Infantry Battalion of the Honourable Artillery Company, part of the 7th Division, in June 1917. In November, the division was ordered to support the Italians against the Austro-Hungarian forces at the River Piave which then formed part of the Italian Front. In late October 1918 the 2nd Battalion captured the island of Grave di Papadopoli on the Piave River for which O'Connor received the Italian Silver Medal of Honour (Medaglia d'Argento al Valor Militare) and a bar to his DSO.
At the end of the war, O'Connor reverted to his rank of captain and served as regimental adjutant from April to December 1919.
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