Winning the lottery: more hassle than it's worth?

A selection of multi-coloured lottery balls, rattling around in a machine such as Camelot's 'Lancelot' contraption.
The balls of fate, yesterday
"I wish I had the chance to do it all over again. I’d be smarter about it now." Evelyn Adams, double lottery winner
  • | by Rachel England

What would you do if you won the lottery? Buy a new pad? Go on a once-in-a-lifetime holiday? Fill your lounge with marshmallows just because you can? The possibilities are endless with millions in the bank, just make sure you don’t fall foul of the circumstances like these people did...

10) A Sicilian winner is scared into silence by the mafia

Could you keep your jackpot a secret? What if your life depended on it? The Italian lottery’s £79 million rollover was won by a Sicilian resident in 2008, but the circumstances surrounding the win – and the winner themselves – are shrouded in secrecy after consumer groups demanded that the windfall be seized by the government.

Even lottery officials have said that it’s highly unlikely the winner will ever go public with their win, because “with that amount of money they would be open to kidnap or extortion from the Mafia”. Yikes.

9) Better late than never for Charles Maginnis

Wouldn’t it be great to avoid the stress of a sudden lump sum and just know that you had enough to generously get by on for the rest of your life? That’s exactly the fortune that befell Washington resident Charles Maginnis who won his city’s ‘Set for Life’ prize, which pays out a tidy $4,000 a week for the duration of the winner’s lifetime. A shame, then, that Maginnis didn’t win until he was a very respectable 82 years old.

8) ‘Giving is receiving?’ Not for Janite Lee

South Korean Janite Lee won $18 million in the Missouri lottery back in 1993, and set about donating sizeable chunks of her wealth to worthy causes – educational programmes, community groups and political organisations all benefited from Lee’s philanthropy. But maybe she should’ve paid more attention to the adage ‘charity begins at home’, because her fervent giving – combined with a gambling habit – landed her in a financial nightmare and she filed for bankruptcy in 2001.

7) Evelyn Adams won not once, but twice

Do lottery winners keep playing the lottery? They must do, since Evelyn Adams won the New Jersey lottery twice, in 1985 and again in 1986, to the tune of $5.4 million. Unable to say no to greedy friends and family, and with a fondness for Atlantic City’s slot machines, Adams blew the lot and now lives in a trailer. “I wish I had the chance to do it all over again. I’d be smarter about it now,” she says.

6) John McGuiness paid the price for love

Scottish football fan John McGuiness won a cool £10 million in 1996 and sank a not insignificant £4 million into his beloved club Livingston FC. The club sank, taking him with it. Further poor financial decisions led to him racking up debts of £2 million in ten years, but he still found a way to keep his £700-a-year golf club membership.

5) Jeffrey Dampier made a killing

In 1986 Jeffrey Dampier won $20 million in the Illinois lottery and generously showered his friends and family with cars, houses and exotic holidays. Some people are just too damn greedy though, and in 2005 his sister-in-law Victoria Jackson and her boyfriend kidnapped and murdered the millionaire ‘out of jealousy’.

4) Callie Rogers: reckless youth

Back in 2003 and at the tender age of 16, Callie Rogers scooped a cool £1.9 million, making her the second youngest lottery winner ever. ‘Youth is wasted on the young’, goes the old saying, and it seems the same is true of money, as Rogers blew the lot on swish holidays, plastic surgery and drugs (including £250,000 on cocaine). By 2009 she was a single mum living with her mother, working as a maid and had twice attempted suicide. Now she’s expecting twins and says she “couldn’t be happier”, which she’s demonstrated by getting her kit off for a weekly gossip magazine.

3) Michael Carroll proves a leopard never changes its spots

In arguably the UK’s biggest case of lottery loserdom, self-styled ‘King of Chavs’ Michael Carroll turned up to collect his £9.7 million winnings wearing an electronic offender’s tag. His new lavish life saw him drain the lot on four prostitutes a day, drink and drug fuelled parties (by the end of 2003 he was smoking £2,000 worth of crack every day) and questionable gold jewellery.

Understandably, his wife left him and took their daughter with her. This didn’t deter Carroll, who became notorious for flipping the bird at neighbours and was later given an ASBO for catapulting ball bearings at cars from his Mercedes. Having blown the lot, he ended up back on jobseeker’s allowance. “I haven’t got two pennies to rub together and that’s the way I like it,” he said.

2) William ‘Bud’ Post III ended up in a real-life thriller

After winning $16.2 million in the Pennsylvania lottery, Bud’s life quickly span out of control.

His brother hired a hit man to assassinate him and his sixth wife (which would suggest his life wasn’t a bed of roses before his win), a former girlfriend sued him in an attempt to get her hands on his cash, his family guilt-tripped him into investing in a business flop, his landlady coerced a third of his jackpot out of him and then he spent time in prison for firing a gun over the head of a bill collector –presumably in an attempt to get some peace and quiet.

1) It never rains but it pours for Jack Whittaker

Pretty much everything that could go wrong did go wrong for Jack Whittaker, who won an almighty $314.9 million in the West Virginia lottery in 2002 (on Christmas Day, no less). His car was broken into twice, the first time resulting in the loss of $545,000 cash, the second with $200,000 (who keeps that kind of money in a car?); two of his employees were found to be conspiring to drug and rob him; his granddaughter’s boyfriend died in his home, then his granddaughter herself overdosed and died, and then, sadly, his daughter died under suspicious circumstances.

He was then charged with drink driving, sued by a casino for bouncing cheques, and sued by a woman claiming he owed her money. He later described the experience as a “nightmare”.