Ernest P. Caggiano, the founder of Ernest P. Caggiano & Son, Inc. Funeral Home, first entered the funeral profession in 1918 after serving in the Army during the First World War, working for a Boston Funeral Service during the great influenza epidemic of 1918-1919. He was then called to duty with the Massachusetts State Guard during the Boston Police Strike of 1919. He was a partner in a tire and battery business in East Boston until 1927, when he opened a funeral home in East Boston. After moving his residence to Winthrop in 1940, Ernest purchased the Richard H. White Funeral Home and Ambulance Service in Winthrop. He and his late wife Grace (Ferrara) Caggiano operated the funeral home and ambulance service; they were joined in 1955 by their son, Ernest C. Caggiano. Grace Caggiano passed away in 1962, and father and son became partners in the operation. In 1970, Ernest P. Caggiano turned the business over to his son, and continued his involvement in the firm until his death in 1981.
Always active in the community, Ernest served as the Chief of the Winthrop Auxiliary Police, Past Grand Knight of the Knights of Columbus, Past Commander of the State Guard Veterans, longtime Sergeant-at-Arms of the Winthrop Rotary Club, and as a member of the Winthrop Lodge of Elks. He was also a member of the Massachusetts Chiefs of Police Association, the Winthrop Chamber of Commerce, the Massachusetts Ambulance Association, and the National and Massachusetts Funeral Directors Association.