The application of a comparative approach in Spanish colonial archaeology is a vital, but infrequent, enterprise that strengthens the historical anthropology of Western imperialism. This chapter compares early Spanish and Anglo-American colonialism in the Marianas and Hawaiian islands. Because these archipelagos were colonized by different Western powers, they offer archaeologists an opportunity to examine colonialism within a comparative framework. Colonialism in the two island groups was markedly different, but this study revealed the following similarities: 1) The indigenous desire for iron in both societies provided them a powerful incentive to provision Western ships, and such trade instigated their engagement with global capitalism, and 2) Western contact attenuated the spatial segregation of gendered labor, thereby altering the household economy. In each case, however, archaeology confirms that these changes were contextually nuanced and protracted.