Henry Cumming may have had commercial interests and business pursuits, but he was first and foremost a lawyer. Cumming started practicing law when he established his own law firm with his partner George W. Crawford. Crawford went on to be a successful politician and was appointed the Attorney General for the State of Georgia from 1827 to 1831, he then served as a United States congressman in Georgia, which eventually led to him becoming the 38th Governor of Georgia from 1843 to 1847.