Reilly was born on 25 March 1882 at Durrington, Wiltshire, the son of Colonel Bradshaw Lewis Phillips Reilly, an officer in the Bombay staff corps, and his wife, Eleanor White. He was educated at Bedford School and entered the Indian army in 1902, transferring to the political department in 1908. He went to Aden, then under the control of the Bombay presidency, as political officer in the Arab town of Shaykh 'Uthman, in the Aden settlement, and remained in Aden throughout the war. He was a member of the delegation to the Yemen led in 1919 by Lieutenant-Colonel Harold Fenton Jacob, assistant resident in Aden, which was intercepted by hostile tribesmen and detained for four months.
Reilly was appointed resident of Aden in 1931. His title changed to chief commissioner in 1932, when the administration of Aden was transferred to the government of India in Delhi, and governor in 1937, when Aden became a British colony, under the control of the Colonial Office in London. The Aden settlement itself covered 75 square miles, but Reilly also had to deal with the Aden protectorate, twenty-five independent states to the north and east of Aden which had signed protection treaties with Britain. As Yemeni raids into the protectorate increased, Reilly persuaded the government that it must honour its treaty obligations and reach an agreement with the imam on the boundary between the Yemen and the protectorate states. In 1933, with Britain and the Yemen close to a state of war, while Yemeni troops occupied the Audhali plateau in the amirate of Dhala and had taken hostages, Reilly was authorized to go to San'a' to open negotiations with the imam, who had accepted a draft treaty. The treaty of San'a', signed in 1934, secured peace on the frontier for a number of years. Britain recognized the imam as king of the Yemen and while the imam never abandoned his claim to the whole of south-west Arabia, on the grounds that the Zeidi imams had ruled there between 1630 and 1730, whereas Britain defined Yemen as the area that had been part of the Ottoman empire, he was prepared to make a temporary settlement, intended to last for forty years. The 1934 treaty marked the beginning of a new phase in the history of the Aden protectorate. Reilly was knighted in 1934.
With the danger of Yemeni raids removed, Reilly turned his attention to internal security in the protectorate. British policy had always been to avoid involvement in internal affairs, but the government could not ignore the interruption of the main trade routes. In 1934 Reilly found money to form groups of tribal guards in each state to police the roads, and trained a force of government guards to escort British officials in the protectorate, and garrison forts on the Aden'Yemen frontier. In addition, there were the Aden protectorate levies, regular soldiers under the command of the RAF regiment. But the bombing of villages by the RAF squadron based in Aden continued to be the favoured method of punishing tribesmen: this was defended by Reilly as plenty of warning was given, there was no loss of life, and the houses were easily rebuilt.
As part of his policy of expanding British involvement in Aden and the protectorate, Reilly appointed a political officer for the protectorate in 1935. He also managed to find government funding for social welfare programmes, including the appointment of an agricultural adviser in 1937. In 1937 he initiated the conclusion of advisory treaties with the main protectorate states, binding the ruler to co-operate with the government of Aden over welfare and development. In 1935 he opened a college for the sons of chiefs and boys from the leading families in the protectorate. It was Reilly who persuaded the British government to take over direct control of Aden in 1937, in response to the desire of the Arab population of Aden to sever the link between Aden and India, worried that Aden might turn into an Indian colony. Although his low-key style meant that he was not widely known outside official circles, Reilly knew how to make the administration work, and he was respected by those who served under him, and revered by the Arabs.
In 1940 Reilly left Aden to join the Colonial Office, and spent the war in London. He continued to be involved in Aden affairs and his advice was often sought. He was present at the Anglo-Yemeni conference in London in 1950 to try to settle recent frontier disputes following the assassination of Imam Yahya in 1948, but there was no hope of a final settlement, and no boundary commission was set up. He also attended the meetings held in London in 1957 on the future of the Aden protectorate. He published Britain and the Yemen in 1960
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