Steadroy ‘Cutie’ Olivero Benjamin obtained his primary education at theGoodwill Academy and upon completion he entered secondary school education at the Antigua Grammar School. He then enrolled at the University of The West Indies(UWI) and in he attained a Bachelors of Arts Degree with Honours in Economics and History in 1974. His Post Graduate studies took him to the United States and England where he gained a Diploma from the United States of America International Manpower Institute as well as a Diploma in Law from the Polytechnic of Central London.

Steadroy qualified as a Barrister when he attended the Council for Legal Education for Bar Final Examinations. In 1980 he was called to the Bar of England and Wales. Throughout his academic career Steadroy Benjamin has been the recipient of many prestigious awards, underscoring the potential that many has seen in him as a youth.

Steadroy’s professional background began as an Air Traffic Control Assistant before he began to apply his technical training via numerous consultancy positions. Throughout his distinguished career he has been at the forefront of labour relations, serving as Labour Commissioner; member of the National Labour Board; Senior Employment Officer in the Ministry of Labour; and as a Hearing Officer in labour disputes. He has also served as a Law lecturer at the University of the West Indies and the Antigua State College.