Malayan career

Upon his graduation from college in 1907, Caldecott joined the Colonial Office in November of the same year and was posted to Malaya. He initially worked in Negeri Sembilan as a Cadet of the Federated Malay States (FMS).^[6] He served as Acting District Officer (DO) of Jelebu from 1909 to 1911. In 1911, he was appointed as Acting DO of Kuala Pilah, and was transferred back to Jelebu to serve as DO in the same year. He was re-appointed Acting DO of Kuala Pilah in the following year.^[7] In 1913, Caldecott was transferred to the Federal Secretariat in Kuala Lumpur and assumed the office of Deputy Controller of Labour.^[6] He subsequently held various positions, including Assistant Secretary (AS) to the Chief Secretary (1914 – 1916), 2nd AS to the Federal Secretary (1916 – 1920) and Acting AS to the colonial government (1920 – 1922).^[7] Caldecott went on leave from September 1922; he took up the ad hoc appointment as Malayan Commissioner at the British Empire Exhibition^[5] held at Wembley Park in the United Kingdom in 1924 and 1925. During the exhibition, he was in charge of the coordination of the Malaya Pavilion. Thereafter, he was conferred CBE by the British government.^[6][8]

After the exhibition, Caldecott returned to Malaya in March 1926 and worked as Town Planning Administrator and State Valuer of Ipoh; he was transferred to the Housing and Public Works Department Enquiry Committees as chairman in December 1926.^[8]

He was appointed Deputy Controller of Labour and Acting Under-Secretary to the Straits Settlements in July 1927, until 1928, when he was promoted to Secretary for Postal Affairs of the Straits Settlements and FMS as Officer, Class 1A.^[9] Since then, Caldecott had been assigned to serve in local authorities; he became Acting Resident of Negeri Sembilan in 1929 and Acting Resident of Perak from 1930 to 1931. He was appointed to serve as Resident of Selangor,^[6] until March 1932, when he was transferred back to the central government of FMS as Chief Secretary. He served as Colonial Secretary of the Straits Settlements from May 1933 to February 1934.^[1][8]

On 17 February 1934,^[10] Caldecott worked as Acting Governor of the Straits Settlements and High Commissioner of FMS, when Sir Cecil Clementi, the then-Governor of the Straits Settlements retired due to illness. During his tenure as Acting Governor, Caldecott upheld Clementi's policy of decentralisation.^[11] He was re-appointed Colonial Secretary when Sir Shenton Thomas took office on 9 November 1934.^[8]

During his time in Malaya, Caldecott earned a reputation for his ability to settle disputes between different ethnic groups which made him popular with all races, a rare feat for a colonial administrator given the diversity of the Straits Settlements population.^[12] He also served as the first president of the Football Association of Malaysia.^{[citation needed]}

Governor of Hong Kong

In 1935, Caldecott was appointed governor of Hong Kong.^[13][14] His tenure was the shortest in Hong Kong colonial history, for he was appointed the second last Governor of Ceylon a little more than a year later to handle the threat to the British administration caused by the overwhelming national liberation movement in Ceylon. When arriving in Hong Kong to assume the Governorship, Caldecott, unusually, elected to wear civilian dress, something that would not happen again until the arrival, in 1992, of the last colonial Governor, Chris Patten. His departure to Ceylon was met with dismay by the community as he had become a respected figure. Locals had petitioned to Foreign Secretary Anthony Eden for him to remain but to no avail.^[15]

It was during Caldecott's tenure that Hong Kong's Kai Tak Airport received its first regular arrival, the "Dorado" and the Queen Mary Hospital opened as an adjunct hospital to the Hong Kong University (the hospital is now under the control of the Hong Kong Hospital Authority). Caldecott called the promotion of Chinese civil servants to replace the European ones, a policy not realized until the signage of Sino-British Joint Declaration in 1984.^[16] His tenure also saw the outbreak of the Second Sino-Japanese War, with more than 100,000 refugees from the Chinese Mainland flooding into Hong Kong to escape the conflict.

Governor of Ceylon

He was sent to Ceylon (Sri Lanka) to examine the situation in the island closely and report on issues such as the governing structure, the representation of the minority communities, the franchise etc. His observations regarding these issues had an important impact on the evolution of the Ceylon constitution.

Caldecott was governor during World War II. During his governance, in 1938, the first diesel locomotive ran to Galle, in 1939, the Bank of Ceylon opened, and, in 1942, the University of Ceylon was established.