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...the next pick to the people who saw you pick the "winner". Now half of those people see one team, the other half see you pick the other team, and whoever saw you pick the winner thinks you've got a 100% accuracy rate over two games. You could do that for a while and then offer to sell your pick for the Superbowl. Starting with a big enough group in the beginning, this might be really lucrative.
But is it legal?
How many coincidences do you need until you believe something to be true?
Science is usually fine with a one in twenty chance (p<0.05, 5 emails) or one in one hundred (p<0.01, 7 emails). Physics is the most strict discipline and requires up to one in three hundred (p<0.003, 9 emails), or even one in a 3.5 million chance (5 sigma, p<0.0000003, 22 emails).
Sure, most mails would be caught in the spam filter anyway and you're not gonna get emails for every single person. And if you have two mail addresses for the same person they'd immediately catch on, once the two addresses get sent different predictions.
But the point is, we are dealing with big numbers here and it is very much reasonable to expect some level of success from such a strategy.
I doubt it'd be any amount of successful. And yes it'd be caught in the spam filter with the other 95% of total emails sent every day.