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Founded in 1526, the Timurid-Mughal dynasty of South Asia was a source of European fascination and interest, to which travelers were drawn by the promise of riches and the exotic. The establishment of direct sea links between Europe and South Asia in the early sixteenth century ushered in an era of diplomatic, commercial, and artistic exchange between these two regions, and saw representatives from Europe arrive at the court of the Great Mughal seeking permission to establish trade agreements beneficial to their home nations. The arrival of English envoys into the Mughal world was due solely to a desire to establish factories, a term used to denote European commercial compounds, within the Mughal Empire, and to have beneficial trade rights and safe passage for their ships in the Indian Ocean waters, then controlled by the Portuguese. It was during the reign of the fourth Mughal padshah, or emperor, Nuruddin Muhammad Jahangir (r. 1605–1627), that the English continuously pressed for these desires. The most well-known Englishman at Jahangir’s court was Sir Thomas Roe, sent as an official ambassador from King James I of England; in actuality, Roe held the dual role of representing the commercial entity of the East India Company. Roe was a prolific writer during his time in Jahangir’s empire, keeping not only a detailed journal but also penning letters to business and personal contacts, and to James I. While Roe’s writings have been used to illustrate the workings of the Mughal court and individual personalities present there, his personality is also revealed. The numerous frustrations and antagonistic relationship with certain members of the Mughal nobility shine through, as does the importance he associated with his position as a royal ambassador. Roe’s constant validation of that role is evident in his writings through the stress he placed on his position at the Mughal court and the intimacy of his relationship with Jahangir. Using the writings of Sir Thomas Roe, in the form of his journal and letters, and the contemporary autobiographical memoirs of the Mughal emperor Jahangir, the Jahangirnama, this study will examine Roe’s self-perceived importance at the Mughal court and the corresponding viewpoint of Jahangir. Jahangir’s stance will be further elucidated through a discussion of significant examples of contemporary pictorial evidence.