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I remember seeing a WWII documentary that described a bet between General Montgomery and an American general (I think maybe Patton) that Montgomery lost, but Montgomery signed the payoff check with such an elaborate reference to the event that the check would have historical significance and would never be cashed.

I can find plenty of online stories about bets Montgomery won, but not the bet I'm thinking of. Am I remembering the bet story correctly?

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  • Perhaps the Race for Messina? Don't know of any bet involving it. Sep 26 at 22:11
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    It would help if you could name the documentary. Sep 27 at 7:19
  • @Lars I can't remember which documentary, but now I would guess it was something related to Market Garden, in which case the American general probably wasn't Patton. Sep 28 at 2:40
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I wonder if you may have misremembered parts of the story. I have an event in mind where the details don't really match up with your recollection, but overall seems to bear a striking similarity.

In 1943, Montgomery and Eisenhower made a 5 pound bet that the war would be over by Christmas 1944. It was actually written down on a sheet of paper, and signed by the two generals:

Agreement entered into, Oct 11, 1943, between Generals Eisenhower and Montgomery Amount £5 - General E bets war with Germany will end before Xmas 1944. Local Time.

This sheet of paper was taken by a widow of one of Eisenhower's staff, who framed it and displayed it in her home for decades. After her death, it was sold for an estimated $20,000 at auction owing to its historical significance.

The bet's significance to Market Garden is that prior to the battle, there was a feeling of optimism and overconfidence in the Allied command. Had the operation succeeded, it was envisioned that the Allies would thrust rapidly across the Rhine and into Germany before the end of the year - which some hoped would mean the end of the war, with Eisenhower winning the bet.

Market Garden's failure put an end to that (before the Battle of the Bulge buried it).

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  • That was one of the many Montgomery-winning-a-bet stories I found while searching, but I'm fairly certain it wasn't the one in the documentary, because that story was a losing bet for Montgomery and the trick was the elaborate check endorsement to prevent cashing, which wasn't done until the bet result was determined. But it's possible I've gotten the details wrong, or the winner-loser are reversed, etc. FYI, Montgomery's own description of some of his (winning) bets are in his memoir. Sep 28 at 14:53

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