In 1958, Harry W. Massey, Sr. founded Massey Insurance and was later appointed as the General Agent for the Massachusetts Mutual Life Insurance Company. In 1969, Franck D. Massey joined his brother in the business. Then in 1979, H.W. ?Hank? Massey, Jr., Harry?s son, joined the organization with brother J. Michael Massey joining several years later. In 1985, Massey Insurance purchased the property & casualty insurance arm of Stockton, Whatley, and Davin.