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I have done the experiment with academics without mentioning that the coin is fair, the result is the same: they assume the probability is 0.5.

You've had an academic sit there and watch you flip a coin 99 times landing it on heads each time?

Yes, because everyone knows thought experiments don't translate to the real world.

But narratives where the conclusion depends entirely on what the author wants aren't even thought experiments. For it to be a thought experiment you'd need to have actually caught some flawed logic and worked out why it was flawed. If the author is trying to differentiate Fat Tony and Dr. John then the author needs the victory of Fat Tony over Dr. John to rely on something other than that the author would prefer Fat Tony to be right instead of Dr. John as the narrative could just as easily have been written the other way.

Here is an alternate ending to illustrate the points:

Taleb: “I am going to flip this fair coin 100 times, and after the 99th toss, I want each of you to tell me the probability of the 100th being heads. You should know that each toss is independent and the that the coin is fair.”

Taleb flips the coin 99 times and each of the 99 tosses results in a heads.

Taleb: “Now before, I toss the coin for the 100th time, I want each of you to tell me the probability of heads on this next toss.”

Dr. John replies in a calm, studied, and restrained tone, “The probability of the next toss being heads is 1/2 (0.5). This is because you originally told me that the coin is fair and each toss is independent of the rest. So, despite the previous 99 heads, the probability of the next toss being heads is unchanged from the beginning (i.e. 0.5).”

Fat Tony replies in a visible excited and somewhat agitated demeanor, “This is one big set up! The next toss HAS to be heads! I don’t trust you. You lied when you told us the initial rules.”

Taleb: "Fine I'll give you 4:1 odds, put up $300 and you can walk away with a cool hundred for catching me in a lie!"

Fat Tony can smell bullshit and never lets his guard down, he takes the bet and already knows where he's going to spend that sweet cash.

Taleb flips the coin and it lands.... Tails!?!

Fat Tony has now fully lost his temper, "You cheated me!"

Taleb: "I told you it had a 50/50 chance of landing on tails, this is a normal result."

You've had an academic sit there and watch you flip a coin 99 times landing it on heads each time?

No. I ask them what is the probability that the next coin flip will land heads.

For it to be a thought experiment you'd need to have actually caught some flawed logic and worked out why it was flawed.

Which I did.

Taleb: "Fine I'll give you 4:1 odds, put up $300 and you can walk away with a cool hundred for catching me in a lie!"

That's 1:3 odds.

Taleb: "I told you it had a 50/50 chance of landing on tails, this is a normal result."

So? You haven't illustrated anything. According to you, you need to show the flawed logic.

No. I ask them what is the probability that the next coin flip will land heads.

So at the end you told them the probability was 50/50 and then asked them what the probability was? Presumably you'd be the one determining if their answer was right or wrong. If they can't trust your premises why should they trust you evaluation?

Which I did.

You did not. Their logic was "I'm going to accept the premise given". You got to decide whether the premise was true or not. The outcome depended entirely whether you decide that the 99 coin flips in a row are the lie(in the form of a coin switch) or the statement about the probability was the lie.

So? You haven't illustrated anything. According to you, you need to show the flawed logic.

It not illustrating anything was the point, I agree I did not show the flawed logic of Tony. I was demonstrating the flawed logic of thinking these stories can be used to show anything at all.

So at the end you told them the probability was 50/50 and then asked them what the probability was?

No, I already said what I specifically did not ask them.

You did not.

I very clearly explained it in the article.

It not illustrating anything was the point

So it had absolutely nothing to do with my thought experiment.