The shit actually goes both ways, many wiseguys also feign poverty because both fellow gangsters and the government would take all of their wealth if they ever found out what they actually have. Like the Chicago mobster who made the government foot the bill for his defense then they go and find nearly $1 million in cash at his place. Some people just don't like going into their own pockets for anything. There are many people who have money but still borrow money, nothing like spending someone else's money. Even me, I have money saved up but given the opportunity to shoplift or skip out on a restaurant I'm taking it.