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It's perfectly possible the bet is good for both sides, just as it is possible the bet is bad for both sides.

You are equating money with utility.

A 1 in 1000 bet that I'll get 1001 times my money back if I play with my life's savings is a terrible terrible bet for me to make even though it has a positive average return. It's also a bad bet for the bookies because they will lose on average.

The larger the cost the more likely it'll be worth taking out insurance.




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