Only one person signed the Continental Association, the Declaration of Independence, the Articles of Confederation, and the U.S. Constitution, and it was a self-taught shoemaker named Roger Sherman. This deep dive traces how a Massachusetts farm boy with only grammar school schooling taught himself surveying, astronomy, and law, published almanacs, passed the bar, and rose to become a Connecticut Superior Court justice, the first mayor of New Haven, and a member of the Committee of Five.

At the 1787 Constitutional Convention, the 66-year-old Sherman made 160 motions and, with Oliver Ellsworth, brokered the Connecticut Compromise that created a population-based House and an equal-representation Senate. The episode explores his distrust of popular passions, his push to ban state paper money, his early opposition to a Bill of Rights, his compromises with slaveholding states, and why history forgot the engineer of American government.

• How surveying, almanacs, and self-taught law built Sherman’s career
• Why John Adams called him as honest as an angel and firm as Mount Atlas
• The Great Compromise that broke the convention’s deadlock
• His views on paper money, the Bill of Rights, and a weak executive
• Why he gave the vice president a tie-breaking Senate vote