Donald Tsang Yam-kuen - tipped as Tung Chee-hwa's successor - has only recently emerged as a serious contender for the post.
Mr Tsang joined the government in 1967 and started on his path to become one of the government's ruling elite during the colonial era as an administrative officer in 1971.
In September 1995, he became the first Chinese to assume the post of financial secretary in Hong Kong, taking over from Sir Hamish Macleod.
When former chief secretary Anson Chan Fang On-sang resigned from the post in February 2001, Mr Tsang was appointed by Mr Tung to lead Hong Kong's 180,000-strong civil service.
His life as a career civil servant came to an end when Mr Tung introduced a ministerial system at the beginning of the chief executive's second term in July 2002.
Mr Tsang joined another 13 principal officials as one of Mr Tung's political appointees.
But Mr Tsang's close ties with the British administration throughout the bulk of his civil service career were seen as an obstacle to his career after the handover.