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Destination Moscow
“They waited until we got to Cairo to tell me we were going to Moscow. I had mixed feelings. I didn’t know if the airplane could go that far and into such a foreign country,” said Vanderkloot. There was little aeronautical information about Russia.

On the first stop, in Tehran, Vanderkloot’s early-hours copilot found that a little knowledge can reveal greater ignorance. Churchill told the story on himself in his memoirs:

“By dawn we were approaching the mountains of Kurdistan. The weather was good and Vanderkloot in high spirits. ... As we descended about 8:30 a.m. on the Tehran airfield and we were already close to the ground, I noticed the altimeter registered 4,500 feet, and ignorantly remarked, ‘You had better get that adjusted before we take off again.’ But Vanderkloot said, ‘The Tehran airfield is over 4,000 feet above sea level.’”

In Tehran, Commando was placed under Russian protection, which was so thorough that Vanderkloot and his crew could not convince Russian sentries to let them within 200 feet of the aircraft. Vanderkloot, staring down the muzzle of a submachine gun, soon forfeited explanations. As he said to Ruggles, “I can tell by the look in their eyes, they’ll shoot us, sure as hell!” Barely in time to prepare the aircraft for takeoff, a sleepy secretary was found who could translate.

Along with Churchill arrived two Russian Air Force officers to help navigate the flight, a welcome sight since the Russians had been known to fire on their own aircraft. These newcomers were startled to see the prime minister take his seat as copilot, but he soon retreated to his passenger seat to enjoy baskets of caviar and champagne and other treats sent from the Russian Embassy. The crew was able to overlook the behavior of the strict Russian guards when it was treated to similar fare, complete with china and waiters, while a Russian crew changed one of the big tires on Commando.

As for Vanderkloot, he reported it took all of his navigational skills to find his way to his bed after an evening of Russian hospitality. However, he never did figure out how a Russian star got pinned to his lapel.

After a three-week trip, Vanderkloot returned his passengers safely to London. It had been a journey of 15,000 miles with the entire Luftwaffe on alert for Churchill, a treasured trophy. In November, Vanderkloot was awarded the Order of the British Empire, a ribbon he was later to use to secure curtains to keep the sun out of Churchill’s eyes, much to the prime minister’s amusement.

The road to Morocco
Later, Vanderkloot flew Churchill to Casablanca for an historic meeting with President Franklin D. Roosevelt, where the unconditional surrender policy was hammered out. In this exotic city, Churchill persuaded Roosevelt to take a side trip to Marrakech. When the time came to depart, he surprised Roosevelt by insisting on seeing him off to the plane. True to form, Churchill wore his colorful dressing gown all the way to the door of the airplane. It was an especially startling garment, with fiery red dragons.

The captain of the American plane stared at the prime minister in his extraordinary costume with a stunned look on his face. He shot a curious glance at the watchful Vanderkloot at the door of his own plane. Vanderkloot, by now accustomed to seeing the prime minister in flashy pajamas and his often spectacular nighttime head coverings, sent back a smile and a wink.

Facing the risks
Vanderkloot safely carried Churchill for three years. By 1945, the crew had flown more than 200,000 miles and more high-ranking officials than any other aircraft in the British service. However, the limits of luck were beginning to be tested. Every plane in the Luftwaffe was gunning for Commando. During a trip to the Middle East, actor Leslie Howard died on a commercial airliner, shot down by the Germans hunting for Churchill.

“The Germans had heard Commando was flying and were shooting everything down that night,” said Vanderkloot Jr.

Soon after, Vanderkloot was returning to London with Field Marshall Jan Smuts. Radio operator Ross Holmes spied two Messerschmitt-109s at two o’clock. One look confirmed the danger.

“There was a cloud straight ahead, two thousand feet below. My father dove for it with all his might,” Vanderkloot Jr. said. “He flew into the clouds and changed direction and the Messerschmitts missed him. It was a close call.”

By 1945, Vanderkloot’s photograph had been in papers around the world, much to his discomfort. According to his son, their home was being watched night and day.

“People were following him in Montreal. He felt it was only a matter of time before the worst happened. It was too risky. … He felt it was time to stop,” said Vanderkloot Jr. But it wasn’t an easy decision.

“Flying Churchill was a wonderful feeling and a wonderful position. I hated to give it up,” Vanderkloot said.

Reluctantly, the British command transferred Vanderkloot and his crew to safer missions. Shortly after, in March 1945, Commando was lost, with all aboard. Vanderkloot returned to the United States in late 1945 to become a corporate pilot. He remained in contact with Churchill, meeting him for lunch in New York after the war.

“Churchill. What a man! He had everything! I was his friend and his greatest admirer, still am and always will be,” Vanderkloot said.

(Bill Vanderkloot passed away April 8, 2000, in Ocala, Fla., at age 85. He was the old, safe pilot he always wanted to be. He granted this interview three days before he died.)