Andrew Caldecott was born on 26 October 1884 in Boxley, Kent, United Kingdom. He was the eldest child of Rev Andrew Caldecott and Isobel Mary Johnson. His mother was the daughter of Rev Stenning Johnson. Lieutenant John Leslie Caldecott (1886 – 9 September 1914), Andrew's younger brother, had served in the Royal Garrison Artillery, who later served as the aide-de-camp to the Governor of Nyasaland. John participated in World War I and died on 9 September 1914 in Nyasaland, Africa (present-day Malawi) at the age of 28, with his remains buried at the Karonga War Cemetery.
Andrew Caldecott studied at Uppingham School in Rutland and was awarded scholarships, enabling him to be admitted to Exeter College of the University of Oxford. He achieved outstanding academic results while in college and had been awarded scholarships. He gained a third class in Classical Honour Moderations and subsequently graduated with a Bachelor of Arts in Classics (second-class honours) in 1907. In 1948, he was conferred as an Honorary Fellow by Exeter College.
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). 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. In 1913, Caldecott was transferred to the Federal Secretariat in Kuala Lumpur and assumed the office of Deputy Controller of Labour. 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). Caldecott went on leave from September 1922; he took up the ad hoc appointment as Malayan Commissioner at the British Empire Exhibition held 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.
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. 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. 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, 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 December 1933 to February 1934. In February 1934, 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. He was re-appointed Colonial Secretary when the new governor took office in November 1934.
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. He also served as the first president of the Football Association of Malaysia.
In 1935, Caldecott was appointed governor of Hong Kong. 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.
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). 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.
Caldecott married Olive Mary Innes, daughter of J. R. Innes, CMG in 1918. He knew his wife while she served as a civil servant in Malaya. She died of illness in Ceylon in 1943. Following her death, Caldecott married Evelyn May Palmer, daughter of Dr J. Robertson and H. Palmer in 1946. Olive bored him a son and a daughter, namely John Andrew Caldecott, CBE (25 February 1924– 14 July 1990) and Joan Caldecott. His son was the Chairman of M&G Group.
Caldecott had a wide range of hobbies. He had published many articles with regards to the affairs of Malaya, and had written books about Malayan history in his early years. In his late years, he published two ghost novels. Besides writing, his other hobbies include drawing, playing the piano, tennis and golf.History of Jelebu, 1912.
Not Exactly Ghosts, 1947.
Fires Burn Blue, 1948.
Awarded M.A. in Oxon
Awarded LL.D. in Ceylon
Malayan Commissioner, British Empire Exhibition, 1924-5
Member, Royal Asiatic Society (M.R.A.S.)
Fellow, Royal Society of Arts (F.R.S.A.)
Honorary Fellow, Royal Philharmonic Society, 1947
In Hong Kong, Caldecott Road, a road in New Kowloon, is named after him.
In Singapore, Caldecott Hill, Caldecott Close, Caldecott MRT Station and Andrew Road are named after him, and Olive Road is named after his first wife.