After 1795 Olenin was employed on a variety of civil positions, including director of the Saint Petersburg Mint (1799). In 1811 he was appointed director of the Imperial Public Library.
From 1794 he took a keen interest in art, in particular, produced a number of graphic works, and formed a large collection of antiquities, which he later (in 1829) donated to the Academy of Arts. He went on to illustrate a number of books, including the selected works of Gavrila Derzhavin and a book of fables by Ivan Khemnitser. In 1804 he was elected a member of the Academy of Arts. In 1806 Olenin published his first scholarly paper, A letter to Prince Musin-Pushkin on the stone of Tmutarakan found at the island of Taman in 1792, in which he deciphered the inscription on the stone. Because of this paper, Olenin is regarded as a founder of Russian palaeography. He is also notable for being the host of one of the most fashionable salons in Saint Petersburg, which attracted many authors, artists, musicians, and actors.
Alexander Pushkin, considered to be the most famous Russian poet, was romantically involved with Anna Olenina, Alexey Olenin's youngest daughter. He wrote a number of poems to her, and even proposed to her in 1828, but was rejected outright. Anna Olenina did not marry until 1840.
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