He was the son of Joseph Caulfield James, the principal tutor to Prince Vajiravudh of Siam.
He was sent to Singapore as his father wanted him to learn English when the only foreign language taught in Bangkok was French.
He attended the Convent of the Holy Infant Jesus (CHIJ) and St. Joseph's Institution.
He was able to do so as the authorities forgot to check his date of birth prior to appointing him as a teacher.
[5] In October, he withdrew from the 1953 Singapore City Council election for health reasons.