In 1723, when Sherman was 2 years of age, his family relocated from his Newton, MA, birthplace to Dorchester (present Stoughton). As a boy, Roger read widely in his spare time to supplement his minimal education at a common school. Sherman received his early education from his father’s private library (not formal school), later attending grammar school. Sherman was a gifted learner, and Harvard educated Rev. Samuel Dunbar took him on as a study. But he spent most of his waking hours helping his father with farming chores and learning the cobbler’s trade from him. In 1743, 2 years after his father’s death, Sherman joined an elder brother who had settled in New Milford, CT.

In 1743, Sherman moved, together with his siblings and his mother, to New Milford (a 175 mile trek) for his father’s death in 1741 left the family destitute. His elder brother had already established himself in New Milford, and so the family had no other options. Not long after the move, he had business in a neighboring town. A short time before, a neighbor had told Roger of a pending legal difficulty. As there was an attorney practicing in the town that Roger intended to visit, he agreed to visit the attorney on his friend’s behalf, convey the points in the dispute, and obtain some legal advice.

Because the subject was complex, Roger had written some fairly detailed notes to assist his memory. When he arrived at the attorney’s office, he stated the case while referring to the notes he had written. The attorney was impressed with the clarity and style of Roger’s manuscript, and said that, with just a few minor changes, it would be equal to any statement of the case he could write himself. The attorney then encouraged young Roger to seriously consider becoming an attorney. At about that time, Roger began a personal study of the law, though he was still very much occupied with the responsibilities of caring for his mother and younger siblings. Not long after, he thought it advisable to leave the shoemaking trade and enter into a business partnership with his older brother, who ran a general store, the first store in the town. Sherman quickly became one of the town’s leading citizens after introducing himself to both civil and religious affairs. Eventually, he became New Milford’s clerk. In 1745, he became a surveyor due to his excellent mathematical skills. At the age of 24 he was appointed to the position of county surveyor for Litchfield county.  As an avid astronomer, he made astronomical calculations for an almanac that was published in New York.In 1748, he was a provider of astronomical calculations for almanacs of the day.

A local lawyer urged Sherman to read for the bar exam even though he did not have any formal training. Sherman was later admitted to the Litchfield bar in 1754 and acted as a representative of New Milford in the General assembly of Connecticut between 1755 and 1758 and again from 1760 to 1761. Sherman was elected to the Upper House of the Connecticut General Assembly and served there until 1785.

In 1762, Sherman received an appointment to serve in the Court of Common Pleas as a justice of the peace, moving on to become a Judge in 1765. Eventually, he left the court for the Congress of the United States in 1789. He also served as a treasurer in Yale College where he received an honorary Masters in Arts degree. He was appointed together with Richard Law to participate in revising Connecticut statutes. After succeeding in these revisions, Sherman was elected as a New Haven’s mayor in 1784. He held this position until his death.

Purchasing a store, becoming a county surveyor, and winning a variety of town offices, Sherman prospered and assumed leadership in the community. In 1749 he married Elizabeth Hartwell, by whom he had seven children (two died in infancy). Without benefit of a formal legal education, he was admitted to the bar in 1754 and embarked upon a distinguished judicial and political career. In the period 1755-61, except for a brief interval, he served as a representative in the colonial legislature and held the offices of justice of the peace and county judge. Somehow he also eked out time to publish an essay on monetary theory and a series of almanacs incorporating his own astronomical observations and verse.

In 1761, Sherman abandoned his law practice, and moved to New Haven, CT. There, he managed two stores, one that catered to Yale students, and another in nearby Wallingford. He also became a friend and benefactor of Yale College, and served for many years as its treasurer. In 1763, or 3 years after the death of his first wife, he wed Rebecca Prescott, who bore him eight children.

Meanwhile, Sherman’s political career had blossomed. One such post was serving as the first mayor for New Haven. He rose from justice of the peace and county judge to an associate judge of the Connecticut Superior Court and to representative in both houses of the colonial assembly. Although opposed to extremism, he promptly joined the fight against Britain. He supported non-importation measures and headed the New Haven committee of correspondence.

Sherman was a longtime and influential member of the Continental Congress (1774-81 and 1783-84). He also served on the Five Committee that was responsible for drafting the Declaration of Independence and aided in the Articles of Confederation, as well as those concerned with Indian affairs, national finances, and military matters. To solve economic problems, at both national and state levels, he advocated high taxes rather than excessive borrowing or the issuance of paper currency. In addition, he served as a new republic’s senator and representative. 

While in Congress, Sherman remained active in state and local politics, continuing to hold the office of judge of the Connecticut Superior Court, as well as membership on the council of safety (1777-79). In 1783 he helped codify Connecticut’s statutory laws. The next year, he was elected mayor of New Haven (1784-86).

Although on the edge of insolvency, mainly because of wartime losses, Sherman could not resist the lure of national service. In 1787 he represented his state at the Constitutional Convention, and attended practically every session. Not only did he sit on the Committee on Postponed Matters, but he also probably helped draft the New Jersey Plan and was a prime mover behind the Connecticut, or Great Compromise, which broke the deadlock between the large and small states over representation. He was, in addition, instrumental in Connecticut’s ratification of the Constitution.

Roger Sherman and Robert Morris were the only two Founding Fathers to have signed all four of the great papers in the United States. These are the Declaration of Independence, the Constitution, the Articles of Confederation and the Articles of Association.

Sherman concluded his career by serving in the U.S. House of Representatives (1789-91) and Senate (1791-93), where he espoused the Federalist cause. He died at New Haven in 1793 at the age of 72 and is buried in the Grove Street Cemetery.

Much of the text and details above comes from these wonderful Resources: 

“A Biography of Roger Sherman,” American History from Revolution to Reconstruction and Beyond.

“Roger Sherman, Connecticut,” Constitution Day.

“Roger Sherman,” Teaching American History.

“Roger Sherman,” The Roger Sherman Society.