How A Russian Prince Became a US Paratrooper and Liberated Sardinia in World War II

An early sketch of Serge Obolensky from the cover of his book, "One Man in His Time: The Complete Memoirs of Serge Obolensky."

When Lt. Col. Serge Obolensky left the U.S. military after World War II, his transition was like many other Americans leaving the service after the war. He started his postwar career with a job working for Hilton Hotels before starting his own company. His prewar life was very much not like anyone else's.

Obolensky was born Prince Sergei Platonovich Obolensky Neledinsky-Meletzky, an Oxford-educated Russian aristocrat who would be close to England's future Edward VIII. His first wife was the daughter of the assassinated Russian Tsar Alexander II, and his prior military experience was as a cavalry officer -- a Russian cavalry officer.

He just wasn't your average paratrooper. By September 1943, he would be an American citizen, making his first combat jump ever. At age 53, he almost single-handedly liberated the island of Sardinia for the United States, his adopted home.

Obolensky wound up in the United States because the country of his birth no longer existed. He left Oxford to become a cavalry officer during World War I, fighting the Germans for the Russian Empire on the war's Eastern Front. When the Bolsheviks toppled Tsar Nicholas II during the war, Obolensky fought the communist Red Army as a guerrilla.

When it became clear the Bolsheviks would be victorious in the Russian Civil War, he fled to London with his wife, Princess Catherine Alexandrovna Yurievskaya.

The Obolensky imperial coat of arms.

He found a job working as a salesman, but his marriage fell apart and the two divorced. Shortly after, he met Ava Alice Muriel Astor, daughter to John Jacob Astor IV, one of the richest men in the United States. Alice inherited her father's wealth after he died aboard the RMS Titanic in 1912. The couple moved to the U.S., and Obolensky joined the Astor family business. In 1931, he became an American citizen.

When the U.S. entered World War II, Obolensky was well beyond military age at 51, but old soldiers never die; he immediately volunteered for the Army. The U.S. Army didn't need old cavalry officers, though. Obolensky was still a wealthy aristocrat with connections. He jockeyed to join the New York State Guard and was accepted as a private, but was still far from the front lines.

When William Donovan, head of the Office of Strategic Services (OSS), the forerunner of the CIA, came to stay at the St. Regis Hotel, Obolensky just happened to be there to meet with him. The St. Regis was an Astor hotel, after all. The two spoke, and Obolensky was immediately inducted into the OSS.

The aging Obolensky was given the code name "Sky" and sent to training with men half his age. As was the agency's tradition, the prince made all five of his qualifying parachute jumps in a single day. His first mission was translating a manual for Soviet partisans into English. His second mission was liberating the island of Sardinia.

OSS founder William Donovan. (National Archives)

By September 1943, Sardinia's Axis garrison included 20,000 Germans and 270,000 Italian troops, a considerable force to fight an Allied invasion. On Sept. 3, 1943, the Allies had negotiated an armistice with Italy's King Victor Emmanuel III and Marshal Badoglio, who had taken over the office of prime minister from the deposed Benito Mussolini. The number of troops on Sardinia posed a real problem for the Allies, especially if the Italian forces continued fighting.

Obolensky and three other OSS commandos airdropped into Sardinia in early September 1943, carrying letters from Gen. Dwight D. Eisenhower and Italian Gen. Giuseppe Castellano informing the Sardinian garrison of the armistice. It was Obolensky's sixth-ever jump and his first combat jump.

After landing, they buried their parachutes and walked into the nearest carabinieri (national police) office, demanding to be taken to Italian Army Headquarters and Gen. Antonio Basso, the Italian commander. He bluffed the carabinieri into believing he was heading a battalion of paratroopers. The policemen took them by truck to avoid German patrols. Upon meeting Basso, Obolensky convinced the general to follow the king's orders.

Obolensky with his OSS team. (National Archives)

The Germans were expelled from Sardinia, and Obolensky radioed back to OSS headquarters that Basso would surrender his 270,000 men. When the armistice was announced over the radio on Sept. 8, 1943, the Germans quickly overwhelmed the Italian armed forces and occupied all of Italy -- except the island of Sardinia.

The Russian prince returned to the U.S. after the war. He had divorced Alice Astor in 1932 and spent his later years working to market luxury brands to Americans through his public relations firm while dating Hollywood actresses. He married for the third time in 1971, but died seven years later at the age of 88.

-- Blake Stilwell can be reached at He can also be found on Twitter @blakestilwell or on LinkedIn.

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Military History World War II