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Why bother insuring yourselves then? Just to cover yourselves incase you get "unlucky"?

Couldn't you structure the contest so that you know you'd payout $X per week and not need insurance?

I guess people eventually could win twice in a short span if they're unlucky and they'd be out of money

Even if somebody won the jackpot only once, I assume they'd be out of money by far, which is why insurance is needed.