The concept of small cities adopted in this article corresponds to urban centres with low relevance in the Portuguese political system. To identify these territorial communities, several classification criteria are suggested (namely the legal status and the political profile of the town) that, after being exploited in monographic studies, may allow conceiving an interpretative model. The most important criterion discussed in this article is the political culture that the concelhos (“municipalities”) preserved in the dialogue they established with the crown. It can be asserted that for the 14th century we have not identified any difference between the discourse delivered by the most important and the less important municipalities in this institutional relationship. This is not the case for the 15th century. Indeed, while small cities keep merely defending the legal order, large cities created an autonomous political identity.