Two Jewish converts to Islam in the service of Bayezid II penned the earliest known anti-Jewish polemicals in the Ottoman Empire. This article aims at exploring the historical context of the two epistles and their connection with Islamic polemical literature. The simultaneous appearances of Abd al-Salam’s Risāla al-hādiya and Abd al-Allam’s Risāla al-ilzām al-Yahūd will be discussed in the context of the Sephardic influx to the Ottoman lands, an encounter that stimulated scholarly interest in the Jewish faith among Ottoman intellectuals. At first glance, the two treatises seem to be structured so as to persuade a Jewish audience to embrace the Muslim faith by abandoning their former religion. However, the choice of Arabic instead of Hebrew, and the circulation of the texts primarily among Muslim readers suggest that ad- dressing the Jews appears to have been a rhetorical tactic. Considering the negative connotations attached to converts by the Ottoman elite, the authors might also have viewed the composition of anti-Jewish treatises as an effort to distance themselves from their Jewish past.