This thesis analyzes an anonymous portrait painting of the Ottoman Sultan Mahmud II (r. 1808-1839), called by its descriptive title Seated Portrait of Mahmud II, within the context of the extensive portrait campaign commissioned by the sultan. Surviving examples from this series of diplomatic portraits share a unique set of intercultural iconographic vocabularies as a reflection of their time as well as implicit reinforcement of the sultan's political goals. By focusing on Seated Portrait of Mahmud II, I argue that a closer inspection of the campaign within a context that pays attention to Ottoman, European, and Persian visual practices reveals a more accurate and comprehensive understanding of its cross-cultural histories and visual as well as ideological references. Structured to reflect the tripartite composition of the artwork itself, this thesis addresses the style and iconographies of the background, middleground, and foreground, respectively. Following a focused examination of the sultan's portrait, I compare Seated Portrait of Mahmud II to two contemporary paintings: Napoléon Bonaparte as First Consul (1808) from France and Portrait of Qajar Ali Shah Seated on a Chair Throne (1807) from Qajar Iran. While bringing attention to the art-historical implications of a hitherto understudied, yet significant portrait of Mahmud II, my work reexamines the early-modern history of Ottoman art within the larger framework of cross-cultural encounters.