Winnings: £9 million (about $14 million)
Time until bust: 5 years
Keith Gough didn’t squander the majority of his windfall fortune — a group of con men did. After Gough’s wife Louise hit the jackpot in 2005, the family spent their wealth normally: they bought a luxurious new home and Gough rented a $560,000 luxury box to watch his favorite soccer team, Aston Villa. But he began drinking “out of boredom” after quitting his job at a bakery, he told newspapers, and his wife left him in 2007. While being treated in rehab, he met James Prince, a dastardly-named con man who convinced Gough to join him in a series of shady business deals, allowing Prince to tap Gough’s bank account to the tune of $1.1 million. Gough was also renting a $1.6 million house and paying annual salaries to a gardener and a chauffeur. But his riches wouldn’t be enjoyed for long: he died in March 2010 of a heart attack, believed to have been brought on by drinking and stress. At the time of his death he still had nearly $1.3 million in the bank.