Using the essays of John Stuart Mill and other classical utilitarians as touchstones, this essay tracks some of the most politically charged shifts in the Victorian political essay, underscoring the significance of issues of racism and imperialism for coming to terms with the genre. The first two sections provide introductory historical background on the cultural and literary significance of the utilitarians, and detail some important ethical and political dimensions of Mill’s philosophical framework. The remaining sections analyse two singularly revealing essayistic encounters: Mill’s exchanges with Thomas Carlyle over the so-called ‘Negro’ question, and Henry Sidgwick’s assessment of the work of Charles Henry Pearson on national life and character. The striking difference between the political essaying of Mill and that of his utilitarian disciple Sidgwick on matters of imperialistic racism is indicative of some of the evasive literary tactics that have been all too influential, from their era to ours.