This chapter traces the origin of the Romanization framework: that is, how the discourse on Romanization sprang up and has taken root in early twentieth century scholarship. Professionalization of the discipline mixed with the deep-rooted gentlemanly tradition stirred new dynamics. Views on Roman imperialism ranged from those of British imperial civil servants to those of American professional academics; approaches varied from the old gentlemanly tradition of exemplary history to new professional academics’ critical history; and evaluations diverged from admiration to disapproval. Despite wide-ranging differences, none escaped from their own social, economic, and political surroundings shaped by European and American imperialism. The comparisons between the ancient Roman Empire and the contemporary British, French, and American empires, either overtly or covertly, underpinned the works of the time.