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He was the son of Fedor Vasil'evich Obolenskii, an army commander in the period 1492- 1522. Ovchina was also a noted military commander in campaigns against Kazan, Lithuania and Crimea. He owed his success to his close place at the court of Vasilii III through his sister, Agrafina. After Vasilii's death in 1533 his widow, Elena (mother of Ivan IV), made Ovchina her favorite and raised him to boyar status. He was a leading commander during the war with Lithuania from 1534-1537, reaching Vilno and Starodub in 1534. In 1535 he led the army defending Smolensk. In 1536 he led negotiations with Kazan and with Lithuania.

In 1537 he led the army that Elena sent to capture Andrei Staritsa and took him to prison. After Elena died in 1538 the rival boyars led by I. V. and V. V. Shuiskii sent Ovchina to prison in the Kremlin, where he died. He was one of the participants in the brutal family feuds that rent the boyars during the minority of Ivan IV.


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