Located on the northern shore of the Black Sea, Odessa is one of Eastern Europe’s great cities. Much has been written about its history. Most of these studies were written from the Russian imperial perspective, and so the city’s Turko-Tatar period has been neglected. The present article attempts to shed light on this period of Odessa’s history, drawing mainly on Ottoman chronicles and archival documents. The predecessor and nucleus of the city was the Karakermen redoubt (palanka), which was built by Mengli Giray Khan I in 1495. Karakermen was destroyed as a result of recurrent Cossack raids in the mid-16th century. Although the Ottomans had intended to revitalise the city by rebuilding the redoubt during the last quarter of the 16th century, this project would be realized only in 1764 with the emergence of the town of Hocabey.