Roger Sherman's trajectory into politics came after he had already established his career in Connecticut as a shoemaker, then a surveyor, then a merchant, then a lawyer, finally a justice of the Peace, before he was elected to the Connecticut General Assembly and appointed Treasurer of Yale College. He became an ardent patriot and represented Connecticut in both Continental Congresses. In addition to his appointment on the Committee of Five which drafted the Declaration of Independence, Sherman is credited with the ‘Connecticut Compromise’ at the Constitutional Convention which established the legislative system whereby the people would be represented by the Lower House of Representatives and the states by the Senate. He was also instrumental in supporting Alexander Hamilton's proposal for federal assumption of the states depts. After Benjamin Franklin, he was at 66 the second oldest member. He went on to serve as a Representative and appointed as a US Senator in 1791. He was considered steadfast and sensible but his colleagues never thought him to be a particularly skilled orator.
He is reported to have arisen every morning at 5am and worked steadily till 10pm. He also was able to find enough time to marry twice and father 15 children.