The article is devoted to the life and career of Prince Ivan Fedorovich Ovchina Telepnev Obolensky, which was restored on the basis of a wide range of archival sources: bit books, chronicles, inventories of documents of the Royal archive of the XVI century and the archive of the Embassy order of 1614 and 1626. Special attention is paid to his fate until 1533, before the death of Grand Duke Vasily III. Much less is known about this period of his life than about the role he played in the reign of Elena Glinskaya in 1533-1538.