Actually, Taleb's approach is like that of the lead character in a book about playing roulette ("Thirteen Against the Bank") that I read years ago. This was about a team who covered every roulette wheel in a given casino (England, then later in Nice, France) at the same time. There were six team members per table, and each bet only on one of the even-money bets (black, red, high, low, even, odd). They used a particular progressive betting scheme that was based on the idea that at some point in a given extended span of time (say, 12 to 24 hrs) there would be a run of results that, combined with the betting scheme, would result in a big win ($>100K). The betting on the other spots would basically cancel each other out (the betting scheme would direct the player having a losing streak to revert back to making minimum bets, while the winning player was steadily increasing the bet) and therefore, when no one even-money bet developed a good winning run, to a minimal overall loss for the team. They wanted to have all the bases covered so that they could take advantage of any extended run of luck on any of the even-money bets. It's a decent story, and many believe it is entirely fictitious. Of course, they did win some good money in the story. I did the numbers and in each case one of the bets had to go on a winning tear of at least 65% winners. So yeah, it was luck, but the question is, what are the odds of at least a 65% winning streak on an even-money bet for, say, 6 hrs straight?
The story took place at a time and in casinos with no maximum roulette bet. So to combat this approach, the casinos use a maximum bet rule (such as $2K on any number and maybe $1K on any even-money bet) on all roulette wheels. You could say that this tells you the team idea has merit.


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