Charles Gibbons began his career in the United States Navy, serving from 1919 to 1925. He then founded The Minute Man Messenger Service in 1932, marking his entry into the private sector. Gibbons transitioned into public service, being elected to the Stoneham, Massachusetts Board of Selectmen in 1941 and subsequently to the Massachusetts House of Representatives in 1942. Over the years, he held various leadership positions within the state Republican party, including Republican floor leader and Speaker of the House. Gibbons also made several bids for higher office, including a run for lieutenant governor and two attempts at the governorship. Despite facing legal challenges, he remained active in public service until his appointment as Commissioner of Administration and Finance in 1961.

Charles Gibbons's political career reveals a unique blend of fiscal conservatism with a surprising advocacy for government transparency and anti-corruption measures. His emphasis on efficient government spending juxtaposes with his strong support for public education and teacher training, suggesting a nuanced approach to public sector roles. Gibbons's military background may have influenced his disciplined, no-nonsense stance on fiscal matters, while his later indictment and subsequent vindication on bribery charges adds a layer of complexity to his public integrity narrative.