Gillon's Scam of the Town
So the way I gather it, Diggs was the favorite and Gillon was supposed to bet the town's money on him, but instead bet on the opponent and drugged Diggs. Gillon gets a big payoff and everyone in town thinks they just lost the bet and don't question.
I get that Diggs was the hometown hero and all, but would everyone in town, save one, really bet everything they own on the favorite? They wouldn't even make even money on the bet.