The Office of Strategic Services (OSS) grew out of humble beginnings and Washington’s political infighting to be a huge part of the American effort in World War II. OSS agents provided important intelligence, furnished operatives who worked behind the lines, and helped resistance and guerrilla movements against occupying German, Japanese, and Italian forces. One of the most successful operations of OSS was the capture of Sardinia, where four American operators convinced more than 270,000 Italian troops to surrender. 

 

The Glorious Bastards

General William Donovan and his band of “PhDs who can win a bar fight” had developed a stellar reputation among the senior Allied leaders. General Dwight D. Eisenhower, the Supreme Commander of the Allied Expeditionary Force, credited the American OSS and the British Special Operations Executive (SOE) with the exemplary manner in which the resistance forces were organized, supplied, and directed. After the war, Eisenhower said,

“In no previous war and in no other theater during this war, have Resistance forces been so closely harnessed to the main military effort…I consider that the disruption of enemy rail communications, the harassing of German road moves, and the continual and increasing strain placed on the German war economy and internal security services throughout occupied Europe by the organized forces of Resistance, played a very considerable part in our complete and final victory.”

General George Marshall, after WWII, wrote how the OSS had far surpassed expectations. “The Resistance surpassed all of our expectations, and it was they who, in delaying the arrival of German reinforcements and in preventing the regrouping of enemy divisions in the interior assured the success of our landings.”

OSS Jedburgh team William Colby
OSS Jedburgh team gather around Lt. William Colby, future Director of the CIA, prior to a mission. (U.S. Army)

A Russian Aristocrat in Sardinia

Sardinia had a garrison of 20,000 Germans and over 270,000 Italians. With the invasion of Italy underway, the Allies wanted to capture Sardinia without having to resort to another full-scale invasion by ground troops. 

It was a tailor-made mission for the OSS. The mission was tasked to a four-man special operations team. General Marshall later wrote that he wanted to “give [General] Donovan a chance to do his stuff without fear of compromising some operation in prospect. If he succeeds, fine, if not, nothing will be lost.”

Chosen to lead the OSS team was the larger-than-life character Lieutenant Colonel Serge Obolensky.

Born a Russian aristocrat, Prince Sergei (Serge) Obolensky had a life full of vicissitudes and varied experiences in both the Russian military under the Czar and the American military. During World War I, he was awarded the highest medals for personal courage as an officer in the Russian cavalry. After the Russian Revolution, the Bolsheviks hunted him. He escaped to America, where he remade himself as a financial advisor to President Roosevelt. He became one of the founders of the U.S. Special Forces, a lieutenant colonel of the Office of Strategic Services, and the oldest combat U.S. Army paratrooper at the age of 53.

Because of his experiences, propensity for languages, and natural ability to influence people, he was a natural for OSS. General Donovan quickly recruited Obolensky into the fledgling agency. 

In early September 1943, the U.S. Army landed at Salerno. Eisenhower wanted the Italian soldiers on Sardinia to surrender and harass the Germans on the island. Obolensky was to carry a letter from Eisenhower, the Italian King Emmanuel, and Prime Minister General Pietro Badoglio to the garrison commander, General Basso, ordering him to surrender. Donovan personally selected Obolensky because he believed the former Russian aristocrat had both the social standing and the gift of gab to persuade the Italian general in charge to surrender to him.

The second member of Obolensky’s four-man team was 1LT Michael Formichelli from New York City. An original member of the Italian-American Operational Group, whom Obolensky had trained with in the U.S., Formichelli was to be the interpreter. The team was rounded out with two radio operators: 2LT James Russell, a special operations instructor at the OSS training school in Algeria; and Sergeant William Sherwood from the British SOE, who would relay information to the OSS base station in Algiers. 

Although neither Formichelli nor Russell had ever jumped from an aircraft, they both volunteered for the mission. Since the OSS had no contacts on Sardinia, this operation would be a “blind jump” into enemy-held territory.

The Coup de Maître

On the night of September 13, 1943, the team parachuted into the island via a blacked-out bomber. They landed safely and buried their parachutes. Russell and Sherwood remained with the communications gear, while Obolensky and Formichelli took off on a 15-mile reconnaissance of the town of Cagliari. 

Warned that the Germans were close, the sight of the two Americans in uniform with submachine guns shocked the Italian townspeople at the nearby railroad station. Yet, thinking that the Americans had arrived to free them from the hated Germans, the Italians began to cheer.

The WWI hero that pioneered US global intelligence

Read Next: The WWI hero that pioneered US global intelligence

Approaching the local police station, Obolensky acted as if he had battalions of paratroopers under his command nearby. He told the police chief, “I have a very important message from the King of Italy and General Badoglio to General Basso. Take me to him!”

Obolensky and Formichelli were escorted to General Basso’s headquarters. General Basso was concerned. Although he agreed to “follow the orders of my king,” and surrender his troops, he did not agree to attack the Germans who were leaving for Corsica and then northern Italy. 

The attitude among the Italian officers was split. Many of them wanted to fight the Germans. However, one unit of paratroopers commanded by a hardcore fascist disobeyed General Basso’s surrender order and shot his representative. The OSS men, including the two radio operators, were kept in a safe house until General Basso and his men could bring the paratroopers back in line. The audacious plan had worked. 

Obolensky radioed back to OSS HQs that “except for the Germans retreating in the far north, Sardinia was ours.”

The mission was a complete success, and it was astonishingly completed in 36 hours without the loss of a single American life. 

Serge Obolensky Marilyn Monroe OSS
Serge Obolensky dances with Marilyn Monroe in the years after the war. (Obolensky family)

Brigadier General Theodore Roosevelt, Jr. arrived a few days later with a small occupation force and formally accepted the surrender of the 270,000 Italian troops on Sardinia. But it was Obolensky and the OSS men who had made it all happen. 

After the war, Obolensky worked for the Hilton Hotel chain and later started his own public relations firm in New York City, Serge Obolensky Associates, Inc. He hobnobbed with celebrities and high-ranking politicians and was photographed dancing with Marilyn Monroe at one of his parties. He died in 1978 at the age of 88. 

The modern-day CIA and U.S. Army Special Forces are the direct descendants of the OSS.

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