Born in Massachusetts, son of a farmer. Roger had no formal schooling beyond the local one-room schoolhouse. He was apprenticed to a shoemaker. His unquenchable thirst for knowledge led him to prop open books on his cobbler's workbench so he could read while working. But at the age of 19, Roger's father passed away, leaving Roger to care for the family. (He was the second-oldest son, but the eldest son had moved to Connecticut.)
He sold the farm and moved the family to New Milford, Connecticut. He continued making shoes. But he got a reputation as a wizard in math, and was appointed to the office of surveyor.
One day, Roger was asked by a neighbor to secure the services of a lawyer, as the neighbor was having some difficulty in settling the affairs of a deceased person. Roger dutifully wrote down all the details so there would be no mistakes once he was in the lawyer's office. He stated the case, frequently referring to his notes. The lawyer, after a time, asked to keep the notes, to better prepare the necessary petition. Roger refused, “These are only notes I wrote down to keep the facts straight. I never intended for anyone to see them but me.”
But the lawyer insisted. Upon reading the paper, the lawyer asked, “Son, are you a lawyer?”
“No, sir.”
“But you've been to law school then?”
“No, sir. Why do you ask?”
“Because the way you've laid out the facts of this case, I could take this very sheet of paper and submit it as the petition. Maybe you should consider the law as a profession.”
So law books were now prominent additions to his cobbler's bench. In 1754 he was admitted to the bar. His reputation blossomed. He was known both for unwavering honesty and common sense. He was appointed Justice of the Peace, later a justice on the county court of common pleas. He was named treasurer of Yale College – and given an honorary degree. Then elected to the upper house in the general assembly of Connecticut.
In 1774 he was elected to represent Connecticut in the continental congress. He was part of the committee assigned to write the declaration of independence in 1776. (Along with John Adams, Philip Livingston, Benjamin Franklin, and Thomas Jefferson) Also in 1776, he was named to the committee creating the Articles of Confederation.
Roger was elected mayor of New Haven, Connecticut (a title he held until his death).
Named to the constitutional convention in 1787. It was Roger Sherman who, in all likelihood, saved the convention when the large and small states bickered over how they should be represented in congress. It was Roger Sherman's “Connecticut compromise,” that saved the day: the House of Representatives would be apportioned by population, but the states would get equal delegacy in the Senate.
Afterward, he returned to Connecticut and fervently worked toward ratification. Elected to the House of Representatives, and appointed two years later to the Senate.
Thomas Jefferson said of Roger Sherman, “...a man who never said a foolish thing in his life.”