Early Life
He was born in Paris as Oleg Cassini Loiewski, the elder son of Countess Marguerite Cassini and her husband, Count Alexander Loiewski. His father was a Russian diplomat, and his maternal grandfather, Arthur Paul Nicholas Cassini, Marquis de Capuzzuchi di Bologna, Count Cassini, was the Russian ambassador to the United States during the administrations of William McKinley and Theodore Roosevelt. In 1918, the violence of the Russian Revolution caused the family to flee for their lives, leaving behind their wealth, lands, homes, nationality and a long lineage which traced back to astronomer Giovanni Domenico Cassini. Cassini recounts seeing his cousin shot in front of him during this time. The family arrived in Denmark, under the Ambassadorial station of Cassini's father, then, to Switzerland. The Greek Royal family invited the Cassini family to Greece. Cassini recounts that on the way to Greece, the train stops in Italy, where newspapers headline the revolution in Greece. The family remained in Italy, settling in Florence.
In his early youth, he suffered a major accident, almost lost his leg, and spent a year in bed recovering, studying history and reading books, authors like James Fenimore Cooper, and developing his love for history and the mysticism of Native American Indian tribes. He discovered American culture through the American movies playing during this time in Italy. He would later quip, "The American Cowboy is the best dressed man."
Oleg goes to school and has to learn to speak Italian. At that time, Oleg only spoke French, Russian and Danish. Oleg is quoted on the subject, “I had to adjust from caviar to linguini”. His mother, Marguerite Cassini, founded her fashion house in Florence with many of the American clients she retained from her days in Washington as the daughter of the Russian Ambassador.
Cassini played soccer with the teenage team, the 'Boys' of Fiorentina, was on the university track team and skied on the university team with childhood friend, designer Emilio Pucci, as well as played tennis for the Italian Jr. Davis Cup team becoming Italian Jr. Champion.
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