Among his siblings was older sister Alexandra Obolensky, the wife of Anatol Nicholas Sazonoff,[1] Princess Luba Troubetzkoy of Sea Cliff on Long Island.
[2] He was a cousin of Prince Serge Obolensky, who married the American heiress Ava Alice Muriel Astor.
[3] In 1917, his family fled to Istanbul from Russia during the Bolshevik Revolution, and in the 1930s, they emigrated to the United States from France.
[5] Obolensky worked as a real estate broker in the Palm Beach area, where he maintained a home.
He co-founded the World Backgammon Club, an organization in Manhattan that sponsors international tournaments, serving as its president until his death.