His business career began in 1962 when he founded John W. Swan Agency, a real estate development and savings and loan company. The services offered included architecture, residential construction, land development, rentals and real estate management. Between 1968 and 1978 the company developed and built 40% of residential homes in Bermuda. Over the years he has helped modernize the city of Hamilton through a number of commercial and residential building projects including the first condominium apartment complex, Atlantis, and his most recent project, 141 Front Street, which is Bermuda’s first 10-storey commercial development at the entrance to the City of Hamilton. Sir John has also been one of the strongest proponents for the development of the Hamilton Waterfront.

Prior to Sir John’s involvement in politics, he was a founding member of the Bermuda Monetary Authority, Director of the Bermuda Chamber of Commerce, and a Director of the Bermuda Employers Council. In addition, he served on several company boards. His political career spanned 25 years. It began when he was elected to Parliament in 1972 and at the same time became Chairman of the Bermuda Hospitals Board. He was Minister of Marine and Air Services from 1975 to 1976. Minister of Immigration and Labour, from 1976 to 1982 and he became Premier in 1982 and served in this post for 13 years. He retired from Parliament in 1997.

Under Sir John’s stewardship, the Government completed in excess of 20 major projects. However, the most significant legacy of his political career was in 1985 when he led the negotiations and the completion of the Tax Treaty with the United States. The Bermuda delegation held several meetings with the most senior officials in the U.S. Government including the President, Vice-President, Secretary of the Treasury, Secretary of State, National Security Advisor and Members of Congress in order to successfully implement a tax treaty between Bermuda and the United States. The agreement resulted in the development of the insurance and reinsurance industries and established the island as a major offshore financial centre, thus creating a foundation for the island’s stable economy, well-developed infrastructure and regulatory framework.

He has received many local and international awards and served on many local and international boards. He was made a Knight Commander of the British Empire (K.B.E.) in 1990 and has been the recipient of three honorary doctorates. Sir John has also participated in several forums such as the Hoover Institution at Stanford University; the Aspen Foundation for Humanistic studies, British Commonwealth Parliamentary Association, World Economic Forums in Davos, Switzerland, Ditchley Foundation Forum in England and in June 2002 was awarded a scholarship to participate in the Aspen Institute Executive Seminar in Aspen, Colorado, USA. His most recent honour was being named Bermuda’s National Hero in June 2016.