The paper examines two Ottoman artists' interpretation of a theme, which has been popular in the history of Islamic book painting. In fact, most of the manuscripts of the Shahnama of Firdausi and the Iskandarnama of Nizâmi, contain a painting which illustrates how Qaydafa (or Nushaba), the Queen of Maghrib, recognizes Iskender, who is visiting her in the disguise of his own envoy, by using his portrait which was made secretly on her order beforehand. In almost all of these paintings, dating from the 15-17th centuries, the "portrait", which shows Iskender in the cliché form of the portraits in Islamic book painting, has been an essential iconographical detail. However, the two Ottoman artists' interpretations of the same topic in the two copies of the Ottoman translation of Firdausi's Shahnama point out the "Ottoman" approach to portrait painting, to Iskender's portrait particularly. The personage depicted in these portraits, in three-quarter view bust form (entirely different from the full-length frontal portraits), with his distinctive facial features, his headgear and outfit, is not an imaginary or casual image of Iskender. Instead, it is a portrait of a real person, the celebrated Ottoman Sultan, Mehmed II. After the comparisons of the portraits of Iskender with that of Mehmed II painted by several Ottoman artists, the paper tries to answer the question why Iskender is transformed and given Mehmed II's identity in the hands of Ottoman artists.