It started with Doug taking 100 bucks from a cookie jar in the kitchen to place a bet on a boxing match with Deaken, much to the disapproval of Carrie, she says no and makes him put it back.
As soon as she leaves Doug takes the 100 anyway, and he places the bet, they win 5000 big ones on the fight but can't buy anything big because the wives would then know what they did, so instead they decide to just blow it all on the town, leaving no assets as evidence.
Almost got away with it too if it weren't for that DMV camera box taking he and Deaken's picture with them in the rented Farrari.