A pioneer public servant in national security who was instrumental in creating the Barbados Coast Guard, Major Sam Headley, who broke the colour barrier as a student in the 1940s, became The Lodge School's first black Head Boy in 1947, in a controversial move by English headmaster T.L. Evans. The son of a bus driver, Headley, from Venture, St John, received an internal scholarship to the mostly white school, then dominated by the scions of planters and merchants. Winning an island scholarship in 1947, Headley attended Codrington College were he graduated with an honours degree in classics, ancient history and modern philosophy.
His application for a teaching post at The Lodge never having been answered, Headley took his skills to Harrison College where for the next 16 years he taught Latin, Greek and English. It was there that he commanded both the Barbados Cadet Corps and the Harrison College Cadet Corps. Reaching the rank of Major in the Barbados Regiment, he became the first Government Security Officer in 1965, responsible for the security arrangements at Independence. As Permanent Secretary of the Division of Defence and Security in the Office of the Prime Minister under Errol Barrow, he played a key role in establishing the Barbados Coast Guard in 1972.
Long-time friend and Lodge old scholar Ralph "Bizzy" Williams described Headley as “a very fine gentleman" with whom he and his family had a "long history".
The industrialist credited Headley with playing a pivotal role in the establishment of his firm, Structural Systems Limited in 1975. Williams recalled: "The Minister of Industry and Commerce at the time made a decision that would have blocked us from starting Structural Systems Ltd. I went to see my eldest brother to tell him that we had been blocked and Major Sam Headley was at dinner at my brother that night and he said, 'do not accept that I will make an arrangement for you to see the Prime Minister'. "He did and the very next week I went to see Mr. Barrow and he reviewed all the documents as we would have applied for fiscal incentives. He commented to Major Sam Headley that this is an excellent project for Barbados and he gave almost immediate instructions for the granting of the duty-free [concessions] to start Structural Systems."
Williams declared that Headley was not given the recognition he deserved from Barbados. He said: "My view was Major Sam Headley never got the recognition that he deserved. He did a lot for Barbados and Barbadians like myself and my brother. My view about Major Sam Headley is that he was an unrecognised hero in Barbados. So, I have tremendous respect for him and later in life, I saw an opportunity to recognise his efforts and we started the Major Sam Headley Scholarship at The Lodge School.” Major Sam Headley was awarded the Queen’s Jubilee Medal and the Errol Barrow Award for his contribution to public service.