This paper offers a re-thinking of the promises, challenges, and the Greek Ottoman perception of the Second Constitutional Period based on a close reading of serialized Rum political satire published in the immediate aftermath of the Young Turk Revolution. Offering continuous, highly-charged commentary –often in verse– on imperial politics and interethnic relations, this vast corpus of Istanbul-based popular literature held subscriber networks stretching across the Ottoman Empire –and well beyond, from Sudan to Paris to California,– but has received almost no critical reading to date. Presenting here a section of my dissertation on late Greek Ottoman popular literature, I discuss the early work, in generational and communal context, of Greek Ottoman satirical poets Konstantinos Makridis, Hristos Deligiavouris, and Brothers Misailidis; and of an avant-garde of Rum political cartoonists who were in their late teens and early twenties when the Young Turk Revolution struck in July 1908. I center the work these Greek Ottoman writers and visual artists produced in late 1908 and early 1909 with a focus on how they reproduced and lampooned the ways –and the specific vocabularies– in which their Turkish compatriots, and the Ottoman state, spoke to and about them. How did the Rum perceive their own perception by the imperial state, and by their Turkish-speaking neighbors, as the sun set over the Hamidian era? What longstanding experiences of sociocultural discrimination and verbal denigration were Rum writers and artists already voicing before the Committee of Union Progress became fully ascendant, and began their Turkifying agenda into state policy? How do the visions and lexicons of interethnic coexistence presented in early constitutional-era Rum popular writing and art complicate long-held scholarly notions of non-Muslim “enthusiasm” or “hopes” or "expectations" for a constitutional revolution? Analyzing also the Greek Ottoman lexicons in describing and satirizing Turks as well as the Empire itself, this paper considers whether the reciprocal vocabularies of alienation and denigration between the two communities (and the Ottoman state) as revealed in such popular literature belies a process comparable to one of racialization, well in progress as early as 1908.