Jack Whittaker was not a desperate man when he bought $100 worth of quick pick tickets at a supermarket in Hurricane, West Virginia, on Christmas Eve 2002. He had spent twelve years as president of Diversified Enterprises Construction in Putnam County and was worth more than $17 million. Then one ticket hit a $314.9 million jackpot, at the time the largest single ticket lottery payout in American history, and he walked away with slightly over $113 million in cash.

This episode follows what that money did next. It starts with real generosity: a tenth pledged to Christian charities, a $14 million foundation for low income families, a house and a car for the deli manager who sold him breakfast. It ends with robberies, lawsuits, the deaths of his granddaughter and daughter, drained bank accounts, and an uninsured home lost to fire. The story is told through the idea of mental accounting, the way people guard earned money and treat a windfall as house money.

• Whittaker only played when the jackpot passed $100 million, and he took the lump sum, leaving him with slightly over $113 million after taxes.
• He bought the deli manager a $123,000 house and a new SUV and handed her a check for $44,000, while also driving a Lamborghini through neighborhoods tossing cash out the window.
• In August 2003 thieves took $545,000 in cash from a suitcase in his car outside a strip club in Cross Lanes, West Virginia. Asked why he carried it, he said he did it because he could.
• Caesars Atlantic City sued him over $1.5 million in bounced checks, and he countersued, claiming he had developed a slot machine for the casino.
• His 17 year old granddaughter Brandi was found dead in December 2004, his daughter Ginger died in July 2009, and in December 2016 his uninsured home in Bland County, Virginia burned down. He died on June 27, 2020, at 72.