This paper examines a number of endowments in the Western Balkan portion of the Ottoman Empire made in the mid-to late sixteenth century by Ottoman officials native to the region. In particular, I examine the endowments of Huseyin Pasha Boljanic (d. 1595) and his brother Kara Sinan Pasha Boljanic (d. 1582), both kapi kullari (“slaves of the gate,” i.e., imperial soldiers) and likely both Poturnaks, that is, recruits for elite service to the Ottoman sultan who were born Muslim and who were native to the region (the word comes from the Bosnian or Serbo-Croatian for “to become a Turk”). A number of primary and secondary sources hint at the possibility that Huseyin Pasha Boljanic was a Poturnak. The chronicler Ibrahim Pecevi refers to him as Potur Huseyin Pasha, a Hercegovinian from the southeastern Bosnian village of Praca who rose from cashnigir (taster) in the imperial palace to beylerbeyi (governor-general of a province). He credits this ascendancy to Huseyin Pasha’s close relationship with Sokollu Mehmed Pasha, one of Bosnia’s most famous devshirme recruits and one of the most famous grand viziers of the Ottoman Empire (term 1565-79). Among other things, Huseyin Pasha endowed one of the most stunning mosques in the Ottoman Balkans, located in Pljevlja in present-day Montenegro. Huseyin Pasha’s brother, Kara Sinan Pasha, was another accomplished Ottoman functionary active in this region. Given that he married Sokollu Mehmed Pasha’s sister, it is likely that he also had a close relationship with the grand vizier. Among other things, he endowed a mosque, a medrese, and an imaret (soup kitchen) in Cajnice in the self-styled Serb Republic of present-day Bosnia-Hercegovina. Scholars such as Behija Zlatar and Enes Pelidija have written about the endowments of Huseyin Pasha and Sinan Pasha previously. This paper aims to add to their work by connecting this endowment history to the history of Poturnaks in the Western Balkan region. Taking into account a number of other endowments made in the same region by Ottoman functionaries who may have been native Poturnaks or had significant connections to Poturnaks, I examine what properties these individuals chose to endow and where they chose to endow them and posit potential motives. In doing so, I offer a preliminary exploration of how Balkan Poturnaks engaged with endowments in their native regions, as well as some of the myths and legacies surrounding these endowments.