“I can calculate the odds of a shark attack,” said Sarah Ledger, Great American’s Director of Betting on Sure Things. “I cannot calculate the odds of a computer convincing a CEO to replace his legal team with a poem about cheese. That is not a risk; that is chaos.”

At publishing time, an underwriter was seen rejecting a tech startup’s application while happily approving a life insurance policy for a man attempting to wrestle a grizzly bear.

Inspired by actual events.