“‘You talk big now, but you wouldn’t if you were sitting at the dinner table with a worm on your plate.’ ‘I bet I would. I’d eat fifteen worms if somebody’d bet me a hundred dollars.’ ‘You really want to bet? I’ll bet you fifty dollars you can’t eat fifteen worms. I really will.’”

Boasting and challenging, the boys talk themselves into a silly adventure. Billy can use $50, so he accepts the bet. The others, especially Alan, who puts up the cash, agree to participate for the sheer joy of watching one of their buddies choke down a slimy worm each day for two weeks. This conversation both lays the foundation for the novel and presents the relationship between the boys and the ways in which its defined by their perpetual one-upping and challenges.

“‘What d’ya mean, it’s not fair?’ said Joe. ‘Nobody said anything about where the worms were supposed to come from. We can get them anywhere we want.’ ‘Not from a manure pile,’ said Tom. ‘That’s not fair. Even if we didn’t make a rule about something, you still have to be fair.’”

To the four boys, $50 is a lot of money, and, even as the worm challenge begins, they start to argue about the rules. It’s a game where a slight mistake—forgetting to eat the day’s worm until 12:01 the next morning, for example—can be grounds for declaring a winner. None of the boys want that to happen to them, but they aren’t above making it happen to the other team. Tom also presents the key debate of the novel when he says that you have to play fair, even if the rules don’t specifically define what “fair” is in that context. Both teams constantly walk this line, often overstepping into territory that is utterly unfair and, despite Tom’s early admonition, using the lack of rules in their favor.