Contest Suggestion: Counter-factual Thinking: Contestants are tasked to create a imagine alternatives to reality. So contestants will be thinking of how things would have gone differently if only... and also what if (i.e. if he had run, would he have caught the bus? or in a world where Rhinoceroses are domesticated pets, who wins the Second World War?). It's a great challenge for the imagination!
In the contest the contestant with the most creative way of counter-factual thinking wins.
Addition: How about contestants enter in pairs, where contestants postulate an alternate world that differs from ours in one key aspect and then post questions to each other. Again, most creative team wins!