Most bookies take all bets and if they can't balance they lay it off on another bookie that will take the other side. Most bookies that run a solid book have enough of a bankroll to weather the storm and simply take the opposite side. The closest thing to a bookie is a market maker, same thing.
Most bookies, including exotic option dealers, will not take action at >50:1 payout. This is my personal experience. This kind of paper is typically one-way.
I trade to make money. Whatever Taleb's intellectual IQ - many in this business have very high IQs - his emotional IQ seems well below average. Taleb criticizes others who are much more successful implying he thinks he's great and others merely enjoy dumb luck, so fine, show us how successful you've been. Besides, since Empirica folded, it shouldn't matter, show us the money. Taleb seems to leak information that he has been very successful through internet pseudonyms, but only people who drank the Koolaid are singing that tune. People who have worked with him through the years claim he sucked at trading. Finally, there is nothing wrong with packing in a mediocre - at best - trading career and retiring. Flogging books and teaching are both respectable, but its bent to claim intellectual superiority and past successes, when neither are merited. Not content to be who he is, Taleb seems needy for undeserved recognition. He opened the door for this type of scrutiny.
What will the argument be after we have a major '87 style event bringing low vol to an end (whether its tomorrow or in 15 years, it will happen again)? I completely agree with most of his arguments, that doesn't mean I agree with his recommendations. Given market conditions over the past 5 years, he would've been hard pressed to make money unless he was buying calls on Asian markets (who said he has to only hedge against catastrophe? BS spends a lot of time talking about black swan successes) In addition, as was mentioned no one will be selling far OTM puts for size anywhere near fair value (even if the value is under-estimated). Here's what I've taken away from the first book and half way through BS: The easiest way to make money in the long run is to manage other people's, running strategies with no black swan protection. This will work until the end of time (I'm assuming the investing public, including the pension funds that manage their money, will always be stuck with short-sightedness and be too greedy to hedge major crash risk sufficiently).