You are right in a narrow sense. Yes, you can construct a situation that makes "betting 99.99% of my wealth" profitable. But:
* You're assuming the winning probability p does not decrease as the odds Y goes up. This is a silly assumption. Do you really believe that the probability is all the same when "Hay I will pay you 2000 livres tomorrow" and "Hay I think I can pay you a infinite amount of livres tomorrow"?
* For example, if p = 1 / (odds), then E(log) never goes to infinity.
If you really assume that there is 1/10000 chance that the mugger can pay you an infinite amount of money, then ...... why not? You can just start a hedge fund on that. You'll gather 100000 people and make them bet independently with muggers, then there is 99.99% of chance that someone actually gets an infinite amount of returns. Now everyone is happy receiving an infinite amount of money.
>You're assuming the winning probability p does not decrease as the odds Y goes up. This is a silly assumption.
No, the only assumption required is that the probability decreases much slower than the odds goes up. Which is self-evidently true; the complexity of the claim doesn't go up nearly as fast as the odds being offered.
If the probability is 1/googol (in reality it's much higher than that, 1/googol epistemic probabilities never show up) but the odds being offered is 3^^^3, then you should take the bet, whether you're trying to maximize wealth or log wealth.
* You're assuming the winning probability p does not decrease as the odds Y goes up. This is a silly assumption. Do you really believe that the probability is all the same when "Hay I will pay you 2000 livres tomorrow" and "Hay I think I can pay you a infinite amount of livres tomorrow"? * For example, if p = 1 / (odds), then E(log) never goes to infinity.
If you really assume that there is 1/10000 chance that the mugger can pay you an infinite amount of money, then ...... why not? You can just start a hedge fund on that. You'll gather 100000 people and make them bet independently with muggers, then there is 99.99% of chance that someone actually gets an infinite amount of returns. Now everyone is happy receiving an infinite amount of money.