[3][2] The world of Sinan Bey and his career is shaped by the reign of Mehmed II, particularly his cosmopolitan vision and tendency towards integrating European visual elements into the indigenous representation of himself and the entire empire, which stemmed from his wish to foster intercultural relations and political alliances.
[5] Raby links this name to the calligrapher ʿAli ibn Mazid al-mushtahir bi al-Saʿati, mentioned in a Muraqqa (album) possessed by the University Library Istanbul, who may be Sinan Beg’s father.
[2] Sinan Bey's training in Italy equipped him with mastery of foreign painting techniques, where he was able to absorb Italian Renaissance stylistic innovations and adapt it to the artistic practices of his own culture (see below).
[8] With that, his artistic practices contributed to creating "an Ottoman pictorial manner that is distinctively Rūmī (i.e., pertaining to the lands of [Eastern] Rome, comprising Anatolia and the Balkans)".
[9] Besides from being an artist, Sinan's occupation as a court interpreter[10] and his continuous, diplomatic undertaking in Venice[11] suggests that he also mastered verbal translation across cultures as he did for visual.
[2] In regard to Sinan's international linkages, Venetian documents record his negotiation on behalf of the Ottomans between 1479 and 1480, demonstrating his diplomatic importance in the court.
[12] Fearing that this unintended attack would destroy the already fragile relationship between the two polities, the Signoria forced Bon to compensate Sinan immediately, knowing that he had a tight connection with the Sultan and thus much political power.
[8] General surviving works of Mehmed II's portraits are quite limited,[13] let alone documentation on those by Sinan Bey and his student Şiblizade Ahmed of Bursa.
[17] Above all, the sultan's facial characteristics in the two paintings are particularly alike, given this Ottoman piece demonstrated the application of modeling and volume, two techniques associated with the flourishing style during the Italian Renaissance.
Some artistic choices in Gentile's painting were replaced by typical stylistic features observed in a Timurid royal portraiture: the frontal, cross-legged pose of the sultan, the iconography of flower, handkerchief, and archer’s thumb ring.
[19] Stemming from its Timurid origin, the flower could entail several connotations such as the sultan's genteel demeanor, refined intellect, and interest in gardens,[20] while the ring around his finger implies his "military achievements and skill as a hunter.