I suppose the gambling may have also had a distinct significance for Fleming himself. Firstly, he was for the longest time dependent on his mother's goodwill and allowance, and probably really considered himself 'poor' - relatively speaking to his class, his fellows at Eton and later the upper crust set he was hanging out with. Fleming didn't come from 'old money', his grandfather had been the one who made the step from working class to wealth, and this particular class often came with a mindset much more snobbish than the 'real' upper class.
Due to a - at the time not unusual - arrangement Fleming's father willed the majority of his estate in a trust to his children. A trust from which Fleming's mother was to draw an income of £ 3,000 a year, as long as she didn't remarry. And she didn't. So in effect Fleming's sons were dependent on her for funds, a crucial influence the highly critical, ambitious and protective Eve Fleming had no qualms to exert as long as she could. So Fleming for the best part of his adult life had to make do with significantly limited funds - compared to most of his friends and acquaintances - and had to appease his mother's demanding nature (who apparently was called "Em" by the boys). There is reason to assume Fleming wasn't a happy man during those years.
Practically his entire life he had been fascinated by wealth, by fortunes and 'the rich' in general; and perhaps deep inside he may privately have held a grudge against a fate that refused him the place in life he felt he rightfully belonged to. With this mindset you look at a pastime where large sums of money change hands in a playful way by a kind of 'gentleman agreement' and under the influence of luck and fate with totally different eyes. Here was something that supposedly provided the riches he did not own himself, although he undoubtedly belonged to the rich part of society. And all it took to succeed here was luck and nerve, so much less than what his mother called for whenever her plans for him didn't work out. Fleming was fascinated by gambling because it seemed to provide - from afar, that is - a way out of his dilemma.
Fleming's fascination for the topic of course also went into his work. But his writing shows gambling in a much more romantic light than reality would allow. He once claimed he didn't gamble often any more and generally won about as much as he lost, or a little more. But the facts of course don't support any stories about supposed riches he made at the baccarat or roulette table. Neither did he excel at that other big casino he briefly worked at, London's City. Luck just wasn't on his side and Fleming was aware of that. Perhaps he also feared the danger of losing all control in the attempt to 'win back' losses, as he doubtlessly had witnessed a few times.
Still, the fascination held and in the end Fleming found a way to use it - profitably use it - and make sure his alter-ego won.
Edited by Dustin, 22 August 2012 - 05:47 PM.