LTC Serge Obolensky and his OSS team. U.S. Archives.
Prince Serge Obolensky, born Sergei Platonovich Obolensky Neledinsky-Meletzky on November 3, 1890, in Tsarskoye Selo, Russia, led a life that was nothing short of extraordinary. From his aristocratic roots in Russia to his daring exploits as an operative for the Office of Strategic Services (OSS) during World War II, Obolensky’s story is one of resilience, adaptability, and bravery.
Early Life and Emigration
Obolensky was born into Russian nobility, with his family tracing their lineage back to Rurik, the founder of Russia. He was educated at Oxford University, where he mingled with English aristocracy, including the future King Edward VIII. During World War I, Obolensky served as an officer in the Russian Imperial Guard, fighting on the Eastern Front against the Germans. In 1916, he married Princess Catherine Alexandrovna Yurievskaya, the daughter of Tsar Alexander II.
The Russian Revolution of 1917 dramatically altered Obolensky’s life. As the Bolsheviks seized power, he initially fought against the Red Army. When it became clear that the Bolsheviks would prevail, Obolensky fled to London. The couple eventually divorced, and Obolensky later married Ava Alice Muriel Astor, the daughter of American millionaire John Jacob Astor IV, who perished on the RMS Titanic. This marriage brought Obolensky to the United States, where he became a naturalized citizen in 1931.
Joining the OSS
When the United States entered World War II, Obolensky, despite being well beyond the typical age for military service, volunteered for the U.S. Army at the age of 51. Initially, he joined the New York State Guard as a private. However, his life took a significant turn when he met William Donovan, the head of the OSS, at the St. Regis Hotel in New York, which was owned by the Astor family. Donovan recognized Obolensky’s potential and recruited him into the OSS.
Obolensky, given the codename “Sky,” underwent rigorous training with men half his age, making all five of his qualifying parachute jumps in a single day. His fluency in multiple languages, charm, and intelligence made him an invaluable asset to the OSS. One of his most notable missions was his involvement in the liberation of Sardinia.
In early September 1943, Obolensky and a small team of OSS operatives parachuted into Sardinia with the mission to convince the Italian forces on the island to surrender. Leveraging his diplomatic skills and the letters from General Dwight D. Eisenhower and Italian General Giuseppe Castellano, Obolensky successfully negotiated the surrender of the Italian troops, preventing a potentially bloody conflict.
While the mission was successful and prevented a potentially bloody conflict, it is important to note that the exact details and the extent of Obolensky’s role may vary in different historical accounts. However, the overall narrative of the mission and its impact on the Allied war effort is well-documented.
Legacy and Later Life
After the war, Obolensky returned to civilian life, working for Hilton Hotels and later starting his own company. He passed away on September 29, 1978, in Grosse Pointe, Michigan. Obolensky’s contributions to the Allied war effort, particularly his work with the OSS, highlight his courage and adaptability. His story serves as an inspiring example of how one individual’s dedication and resourcefulness can make a significant impact on the course of history.
Resources
Central Intelligence Agency
CIA.gov
USASOC OSS Website (Official US Army Website)
www.soc.mil/OSS/index.html
The OSS Society
OSSSociety org