BY THE SUMMER OF 1941, OPERATON BARBAROSSA, Hitler’s bold plan for the invasion of Soviet Russia, was in full swing. With the Soviet armies in retreat, Hitler invited his Italian ally, Benito Mussolini, to fly with him to the war zone in his Fw 200 Condor, the Immelmann III. The journey would allow Hitler to savor his triumphs in the east and to view the conquered Ukraine, where his Army Group South had destroyed 20 enemy divisions and taken over 200,000 prisoners. Hitler firmly believed that Joseph Stalin and his Bolshevik regime now faced extinction.

The trip to the Ukraine called for a flight of over 600 miles to an airstrip at Uman´, in an active sector of the front 150 miles south of Kiev. The weather proved ideal—little turbulence and a nearly cloudless sky. Joining Hitler and Mussolini for the flight were Nazi Foreign Minister Joachim von Ribbentrop, SS head Heinrich Himmler, and the Italian ambassador to Germany, Filippo Anfuso. Santi Corvaja in his Hitler and Mussolini, The Secret Meetings, records Anfuso’s vivid account of the unspoken anxiety aboard: “They were all thinking of the front pages of the newspapers had we all crashed together.” The Soviet air force had been nearly destroyed, so it posed no real threat; still, the Luftwaffe deployed an escort of Messerschmitt Bf 109 fighters to ensure the Führer’s safety.

But Hitler and his personal pilot, Hans Baur, encountered another danger: On the return leg, Mussolini asked his German host if he could fly the airplane. Mussolini had earned his pilot’s license in the pre-war years and fancied himself a talented aviator. Hitler acquiesced but prudently instructed Baur to remain at the controls.

Once Mussolini entered the cockpit, Hitler nervously returned to his Führersessel (special leader’s seat). Under the watchful eye of Baur, Mussolini put the Condor through several shallow banks and other maneuvers and expressed great admiration for the airplane’s responsive controls. After an hour, Mussolini finally returned to the cabin, to the relief of all. Anfuso wrote of the incident, “I’m sure the joke was not at all to Hitler’s liking. The SS must have thought of it as an attempt to murder the Führer. Not knowing what to do, they stared blankly at Himmler, who kept silent. When the time came to land, Hitler’s pilot…told the Duce landing was not such a good idea. Mussolini turned and saw the convulsed faces of the passengers, who having so far avoided death at the hands of the Soviets did not want to die because of an Italian, however famous he may have been.”

Much to Hitler’s annoyance, Mussolini then instructed an aide to mention in a joint communiqué from the two Axis leaders that the Duce had flown the Führer home from the front. Mussolini’s posturing as an intrepid aviator could have been a scene in a classic movie: Charlie Chaplin’s 1940 parody, The Great Dictator.

Despite the comic opera aspects of Hitler and Mussolini’s aerial odyssey to the Russian front, both men took aviation very seriously. Along with Stalin, the other high-profile authoritarian ruler of the era, they shared an enthusiasm for aviation as a way to showcase national technological progress. Mussolini, Hitler, and Stalin fully comprehended the mystique and powerful public appeal of aviation and exploited the technological marvel of the age—the airplane—for their peculiar ends, including taking to the air themselves.

Mussolini: The Winged Despot

Mussolini displayed a keen interest in aviation as early as 1909, when, as a young socialist and journalist, he had heralded the attempts to fly across the English Channel (with Louis Blériot succeeding) as a portent of the future. He viewed flying machines as more than a novelty or the plaything of the wealthy, arguing that the airplane was destined to alter the course of history.

The stalemate of trench warfare in World War I only deepened his respect for flying. As a soldier, he marveled at the freedom and heroism of pilots, in particular Italy’s own Gabriele d’Annunzio, who made a dramatic bombing raid on Austria’s capital, Vienna. After the war, Mussolini took great delight in hobnobbing with military pilots, taking airplane rides, and promoting the advance of Italian aviation.