5 Dollars Roger Sherman

Roger Sherman was the only Founding Father to sign all four of the major documents establishing the United States: the Articles of Association, the Declaration of Independence, the Articles of Confederation, and the Constitution. His Connecticut Compromise of 1787 broke the deadlock between large and small states over congressional representation — without it, the Philadelphia Convention likely collapses entirely.

Barbados has quietly built one of the more coherent series of American Founders issues among Caribbean mints. Sherman, perpetually overshadowed by more celebrated contemporaries, makes for an unusual and defensible choice.