David Samuels tells the story of Jack Whittaker, who in 2002 won "the biggest single undivided jackpot in lottery history" – $314.9 million. Whittaker was a successful businessman before the win, but ten years later he had lost most of his family to drugs, alcohol or divorce and wished he'd never won:
Whittaker’s transformation from successful businessman and loving grandfather to disheveled and obnoxious strip-club patron took less than two years and alienated many of his friends and family members—beginning with his wife, who soon filed for divorce. While a reflection of Whittaker’s own flaws, such personal upheaval is more common than not among jackpot winners, according to Mike Kosnitzky of Boies, Schiller & Flexner, a law firm in New York. Kosnitzky has been involved in the representation of half a dozen large lottery winners; his clients include a former attendant at a parking garage in Midtown Manhattan named Juan Rodriguez, who in 2004 won a Mega Millions jackpot worth $149 million.
In his experience, Kosnitzky says, most lottery winners suffer tremendous guilt as the result of their good fortune; they’re also troubled by family members and friends who feel entitled to their winnings and who become angry when they don’t get what they feel they deserve. Without access to financially and psychologically sophisticated advice, winners quickly find themselves easy marks for every kind of manipulation and often take refuge in preexisting addictions, which are compounded by seemingly inexhaustible wealth.