The recent rise of perpetual trusts has brought new attention to previously obscure state constitutional prohibitions of perpetuities. This symposium commentary examines the historical origins of the first such prohibition, Clause 23 of the 1776 North Carolina Constitution and Declaration of Rights, which provided that “perpetuities and monopolies are contrary to the genius of a free State, and ought not to be allowed.” Although many good reasons can be offered for the provision, it is curiously absent from the constitutions of the twelve other original states. Why did this provision emerge only in North Carolina, and not in Virginia, Massachusetts, Pennsylvania, or any of the other “free states” that together rose up against their colonial masters? This commentary suggests a possible answer to that question. Although the problems with perpetuities were well known to learned inhabitants of all the newly independent American states, those problems were particularly salient in North Carolina in 1776 due to that colony’s unique history as a former proprietary colony. The decision by the heir of one of the original Lords Proprietors not to sell his share back to the British crown gave rise to specific grievances in North Carolina that did not exist in the other twelve former colonies. Moreover, North Carolina was unique in witnessing a violent confrontation between the colonial authorities and backcountry farmers that stemmed in part from those grievances. The peculiar case of the Earl Granville and assorted problems in his Granville District shifted the problem of perpetuities from the periphery to the center of North Carolina politics in the late eighteenth century, and made perpetuities warrant an explicit mention in the 1776 North Carolina Constitution and Declaration of Rights.