A less-appreciated aspect of earlier or “classical” works of world-systems analysis (WSA), in particular that of Braudel, Frank, and Wallerstein in the 1970s-80s is the examination of why the thirteen North American colonies that became the United States split from Great Britain. Specifically, why did some of Britain’s North American colonies revolt in the mid-1770s, but not others? Why were some colonists pro-independence while others preferred remaining within the empire? Classical WSA suggested regional differentiation among colonists, and later works in the WSA tradition have examined these divisions in British North America, particularly within individual colonies, based on both larger divisions in the world-economy and localized core-periphery structures. Yet classical WSA’s analytical questions about British North America’s independence movement have been more directly addressed by historical geographers. This paper synthesizes classical WSA with works on the historical geography of British North America, and then examines the synthesis in light of colonial New York and its political-economic geography of several distinct regions, each with varying economic and political interests vis à vis the British Empire and the question of independence.