Bradman Weerakoon has the unique distinction of serving nine Sri Lankan heads of state in a career spanning across half a century.

He obtained a Bachelor's Degree with second class honors (upper division) in economics and sociology from University of Ceylon and was awarded a Fulbright scholarship to study in University of Michigan for one year where he did his MA in Sociology.

Bradman joined the Sri Lankan civil service in 1954 as an understudy to the Government Agent of Anuradhapura, after which he spent a year in Jaffna where he learnt Tamil. After that he was transferred to Badulla but before he could assume duties, the order was withdrawn and he was sent to the Prime Minister's office.

In 1953, he was appointed as the assistant secretary to the prime minister at the time, Sir John Kotelawela. He later became his secretary and continued after Solomon Bandaranaike became the prime minister in 1956. After his death, he served Vijayananda Dahanayake and Sirimavo Bandaranaike. Thereafter he worked for Dudley Senanayake although some in the UNP felt uneasy about his presence. After Sirimavo won the election again in 1970, his secretarial career came to a halt and he was transferred to Batticaloa and later Ampara. In 1976, he retired from his post to join IPPF, an NGO working in the area of family planning.

In 1977, J.R. Jayawardene appointed him as the secretary to the ministry of plantation. In 1980, he joined then Prime Minister Ranasinghe Premadasa's staff as secretary. Following the ethnic riots of 1983, he was appointed as commissioner-general of essential services with wide ranging administrative powers. In 1984 he re-joined IPPF as its secretary-general in London for one year, which entailed a great deal of travel from China to Africa to Mexico.

Following President Premadasa's assumption of office he was appointed presidential advisor on international affairs during a period when Indo-Lanka relations were at its lowest, following the expulsion of the IPKF.

After Premadasa's death, he remained as his successor Wijetunge's advisor and resigned in 1994 when Chandrika Kumaratunga became the president.
After Ranil Wickremesinghe became the prime minister in 2001, Bradman was offered his familiar position of secretary, which he reluctantly accepted. His memoirs, Rendering Unto Caesar, was published in 2004.