A former Cabinet member having served as the Minister of Works, Engineering and Housing, Ashfield was Bermuda's representative in the United Nations for the Southern Countries on the Sustainable Development Commission (with emphasis on science and technology).

Ashfield is currently the Program Director of The C.A.R.E. Learning Center ("CARE"), which assists young and mature students in achieving a high school diploma. His experience as an adult student at Bermuda College has given him an understanding of the challenges that mature students face, making him ideal for the position he currently holds at CARE.

Ashfield has an interesting and varied background in the communications field, having spent 14 years at Cable and Wireless Limited where he served as Network Management Supervisor with responsibility for ensuring the quality of service of the company's international telephone network. However, he may be best known as an on-air broadcaster, particularly for his comprehensive daily reports from the local courts, and as co-host of the highly rated nightly radio talk show, "Night Talk" with Ceola Wilson.

A long time resident of Constituency 21 and former executive member of the Friswells Hill United Group, Ashfield’s current residence at the corner of Court and Angle streets has allowed him to have a firm grasp of the issues and concerns of his constituents. As the candidate for Pembroke South East, he vows to continue to work closely with Government, The Corporation of Hamilton, area residents and business owners to ensure the success of the new North Hamilton Empowerment Zone Initiative and to encourage area residents to participate in Corporation of Hamilton municipal elections.

He also looks forward to continuing his work with Government and the police service in addressing the basic needs of his community, including addressing the issues involving anti-social behaviour and improving the collection of court ordered child maintenance payments for all primary care givers.