This article explores a unique series of caricatures made between 1884 and 1896 by Yusuf Franko Kusa, a high-ranking Ottoman bureaucrat and a venerated member of fin-de-siècle Pera's high society. Yusuf Franko's hitherto unstudied caricatures were comparable to contemporary European caricatures in style, but their subject matter was very local, as he exclusively represented the elite networks that built and enjoyed "cosmopolitan" Pera, one of the central districts of late Ottoman Istanbul, in his art. These caricatures were never published, but bound as an album by the artist himself and circulated among Yusuf Franko's entourage, members of elite society of Pera. Through close scrutiny of Yusuf Franko's drawings and especially of the absences in them, the article provides a visual mapping of Pera's social topography and explores what images can show that is sometimes ignored in textual sources. It is argued that the satirical form and the inter-visual references employed by Yusuf Franko to represent his inner circle promise to unravel the complexities embedded in Pera's society, with more nuanced criticisms towards his fellow elite members than the conventional literature on Pera. Yusuf Franko appears not only as an illustrator of urban life in fin-de-siècle Pera, but also an active participant in the making of this urban life through his playful acts of elite community-building, i.e., the informal and underground circulation of the images within high society. This article thus attempts to show one particular way in which visual sources can be treated as historical agents themselves, as well as serving as sources for (urban) history-writing.