During the Khmelnitsky Uprising and from the early days of its existence, the Cossack state emphasized its intolerance toward the Jews and their participating in leaseholding. Yet, already by the end of 17th century and the beginning of 18th century, a considerable number of them were living in Cossack Hetmanate as local leaseholders. The history of Jews and their settlement in Cossack lands got little attention in the historiography of East-European Jewry, usually treated as an episode of Jewish history in Russian Empire. So, until this day there is no comprehensive study on the subject. In my research, I try to answer following questions relating the factors that enabled the migration of Jews to Cossack Hetmanate in 17th and 18th centuries, and how the Jewish settlement developed there during this period. In my research, I focused mostly on Jewish leaseholders because leaseholding was the main occupation among them. While analyzing various sources, it became obvious that the declining power of the central government, which followed be the growth of the manorial system and the development of alcohol industry allowed Jews to dwell in Cossack Hetmanate. However, because the resentment toward Jews still dominated the Cossack society, the Jewish settlement developed in its unique way. It was mobile, constantly changing population and without any familiar Jewish institutions. In conclusion, the story of Jews in Cossack Hetmanate allows us to broaden insight on the migration processes and the ways Jews adapted to various social environments.