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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.”

What is more likely? That a fair coin lands heads 99 times in a row, or that Taleb lied? Fat Tony doesn’t need to be very intelligent to know the answer: his experiences in life have given him the wisdom to distrust claims like this. Dr. John may have more knowledge about probability, but not about deception.

Fat Tony can smell bullshit and never lets his guard down.

Using a contrived example to warn us against trusting contrived examples. Either outcome is a gotcha. Only fair move is to not play. and the outrage fat tony has should apply to the OP as well.

Fat Tony is basically a contrived pastiche that is used for this purpose throughout Taleb. He's an annoying device for exactly this reason, and I like Taleb.

He comes across as less contrived when you've actually met a few Fat Tonys in real life.