Did a £5 bet nearly cost the Allies the Second World War?

It is as commander of the British Eighth Army in the Western desert during World War 2, and later as commander of Allied ground forces in Operation Overlord, the invasion of Normandy, that Bernard (‘Monty’) Montgomery is perhaps best known. What is less well known is that he loved to wager on almost anything. One of the best documented examples was Monty’s bet with Walter Bedell (‘Beetle’) Smith, later Chief of Staff of US General Dwight (‘Ike’) Eisenhower, that the Eighth Army would capture the strategically important Tunisian port of Sfax by April 15th, 1943. The terms of the wager were that the Americans would, if he was successful, deliver him a B-17 Flying Fortress, complete with an American crew. Sfax fell on April 10 and Montgomery cabled Eisenhower immediately, demanding full and immediate payment. Montgomery got the Flying Fortress but not before receiving a stinging dressing down from the Chief of the Imperial General Staff, General Alan Brooke (later Viscount Alanbrooke). So we learn from Alanbrooke’s diary entry for June 3rd, 1943. Smith is reported to have later remarked to Monty: “You may be great to serve under, difficult to serve alongside, but you sure are hell to serve over.” Still, the days of the wager were not over, as evidenced by the £5 wager struck between Montgomery and Eisenhower about the timing of the end of the war. Eisenhower describes the bet in his memoirs as follows: “I was personally so confident that we could launch ‘Overlord’ strongly and promptly in the spring of 1944 that I bet Montgomery five pounds that we would end the war by Christmas of that year. I lost the bet.” Now one of the potential pitfalls of betting comes about when one party to the wager has inside information that the other does not, or when one of the parties can influence the outcome in a way the other is unaware of. So could this £5 bet have influenced the timing or perhaps even the outcome of the Second World War? Can a man be so obsessed with winning a wager that he would be prepared to lose a war? Of course not! We are talking the real world here. As Eisenhower himself relates, he lost the bet because he failed to take account of two things. “The first of these”, he writes, “was the late date of the assault across the Channel, and second, was that I did not conceive that Hitler would continue fighting after we had once lined up the Allied Armies on the banks of the Rhine.” No, a £5 wager had absolutely no impact whatsoever on the conclusion of the war. Now make it a Flying Fortress and we might be talking!