Born and schooled in Terryville, Henry Brophy became a sportswriter for the Waterbury Republican in the mid-1920’s. During some of this time, he managed the Thomaston Ponies, a semi-pro football team which won state titles, and played against the Bristol West Ends. Brophy later managed the West Ends during that club’s heydays in the mid-to-late 1930’s. Brophy later took on the assignment of the PR man for New Departure.
During the 1940’s, he was part of a Bristol sports organization that brought pro baseball and football teams to play exhibition games at Muzzy Field. Many of those teams included future Hall of Fame managers and players. He was involved in many sports at New Departure, where employees played in both company and city leagues. He was a sports contributor to New Departure News, the company publication, and wrote a history of New Departure sports for the 100th anniversary edition of the Bristol Press in 1971.