He was elected to the Florida House of Representatives in 1928 and served from 1929 to 1931. During his term, Pepper served as chairman of the House's Committee on Constitutional Amendments. In response to the Great Depression, Governor Doyle E. Carlton proposed austerity measures including layoffs of state employees and large tax cuts. Pepper was among those who opposed Carlton's program, and popular support was with Carlton, so Pepper was among many legislators who lost when they ran for renomination in 1930.