In 1946, the economist Maurice Dobb published a book that attempted to explain how feudalism gave way to capitalism. Dobb’s book began a debate among economists and historians that has continued until this day. Dobb thought that feudalism went into decline and was replaced by capitalism because of endogenous causes rooted in the class struggles between serfs and noblemen. An early and prominent critic, Paul M. Sweezy, thought that the factors which led to the decline of feudalism and rise of capitalism were exogenous, and these factors included the development and growth of international trade, production for markets and money, the growth and importance of cities, and the need for European monarchies to unite their kingdoms and to finance their wars and overseas empires. This paper does some preliminary empirical testing of these hypotheses using data from Britain from the 1200s to the 1800s. The findings of this paper are informative in trying to better understand the debate and provide some food for thought on how capitalism may change in the future.