Wartime leadership is not usually remembered for friendly bets, but one such story reportedly emerged in 1943 involving Dwight D. Eisenhower and Bernard Montgomery. According to the account, Eisenhower ultimately honored the wager by giving Montgomery a Boeing B-17 Flying Fortress. He was reportedly surprised—and not particularly pleased—that Montgomery decided to take possession of the aircraft rather than decline it.
The episode is also said to have attracted the disapproval of George S. Patton, who reportedly viewed the outcome unfavorably and expressed dissatisfaction with the way the matter was handled.
Bernard Montgomery in North Africa
By 1942, Bernard Montgomery engaged in a hard-fought campaign battling against Generalfeldmarschall Erwin Rommel across the deserts of North Africa. Although Allied forces were steadily driving the German enemy backward, the campaign came at a high cost in both manpower and resources.
Determined to keep Rommel under constant pressure, Montgomery called for additional soldiers and supplies. His view was shared by the other Allied nations, which recognized that securing North Africa was essential before they could successfully launch an invasion of Italy.
Operation Lightfoot
This was the reasoning for Bernard Montgomery’s Operation Lightfoot. Launched late on October 23, 1942, it was designed to knock Erwin Rommel out of North Africa, once and for all. Months of deception had fooled the Germans, allowing the Allies to keep where the operation would take place a secret. This was done through fake ammunition dumps, dummy tanks and supply trucks.
At 9:40 PM, an enormous 1,000-gun artillery barrage marked the beginning of the assault. Thousands of troops and hundreds of tanks advanced toward the Germans, causing them to retreat in a panic. Not long after the attack began, Operation Torch brought 73,000 Allied soldiers onto Africa’s northern shores to push the Germans east.
The Allies and Axis powers clashed, while George Patton and Montgomery raced each other to liberate cities and territories. They were making excellent progress, but Dwight D. Eisenhower wanted more. A couple of months into the offensive, he sent Maj. Gen. Walter Bedell Smith, his chief of staff, to visit the British general at his headquarters.
Betting a Boeing B-17 Flying Fortress
During a meeting in 1943, Bernard Montgomery asked whether he might receive a Boeing B-17 Flying Fortress to use as his personal transport aircraft. Walter Bedell Smith reportedly responded with a joking challenge, saying that if Montgomery could capture the Tunisian city of Sfax by April 15, 1943, the bomber would be his.
What Smith meant as a lighthearted joke was taken seriously by Montgomery. His forces captured Sfax on April 10—five days before the deadline—and he quickly reminded Dwight D. Eisenhower of the wager. True to his word, Eisenhower honored the agreement, providing Montgomery with a B-17 along with a crew to fly and maintain the aircraft.
George Patton wasn’t happy about the bet
12,731 B-17 Flying Fortresses were built during World War II, making the association of a single aircraft with Bernard Montgomery seem relatively unremarkable at first glance. Nevertheless, the arrangement reportedly became a source of irritation among several senior Allied leaders.
According to the story, Dwight D. Eisenhower was unhappy that Montgomery chose to keep the aircraft, particularly at a time when bombers were in constant demand and combat losses remained substantial. George S. Patton was also reportedly displeased, believing it unfair that a British commander had access to a dedicated aircraft for transportation while he was required to rely on whatever transport could be arranged as he traveled between commands.
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Ultimately, the controversy had little lasting significance. Roughly a month after Bernard Montgomery received the Boeing B-17 Flying Fortress, the aircraft was damaged in a crash landing. Following the accident, Dwight D. Eisenhower did not provide a replacement, bringing the episode to a quiet conclusion.