Paternally, he belonged to the Obolensky family of Russian princes who trace their lineage to the Rurikid rulers of Kievan Rus who preceded the Romanov emperors.

Obolensky was educated at St. George's School in Middletown, Rhode Island, and graduated from Yale College in New Haven, Connecticut, in 1947.

After Yale, Obolensky became a writer working for Telavid Inc. Imports, and went on to serve with the United States Navy as a pilot.

Throughout his main career on Wall Street as a financial analyst, Obolensky covered many prestigious accounts.

[7][8] Claire was educated at the Convent of the Sacred Heart and at Miss Burke's School, both in San Francisco, and at Finch College in Manhattan.