Want to win the lottery? Some words of caution: It ain’t always a “win.” (This article was first published in Uncle John’s Curiously Compelling Bathroom Reader.)

Christina Goodenow of White City, Oregon

PRIZE: $1 million
WHAT HAPPENED: On October 12, 2005, Goodenow played the Oregon Lottery’s Million Dollar Jackpot Scratch-It game…and won. Two weeks later she was arrested. It turned out that she’d purchased the ticket with a stolen credit card—her deceased mother’s. The Oregon Court of Appeals ruled that because the ticket was fraudulently purchased, Goodenow could not collect the winnings.

Johnny Rae Brewster of Dallas, Texas

PRIZE: $13 million
WHAT HAPPENED: Brewster won the Texas Lottery jackpot in 1995…and died 10 months later of a heart attack. His will stipulated that his sister gets his lottery winnings, but she inherited something else: his $3.5 million tax bill. Under Texas law, the estate has to pay all taxes owed by the deceased in full immediately, even though Brewster’s annual lottery payments were only $460,000. Fortunately, the sister and the state struck a deal: she could pay $482,000 a year for 10 years, which meant she actually lost $12,000 a year because her brother won the lottery.

Michael Carroll of Norfolk, England

PRIZE: £10 million (about $18 million)
WHAT HAPPENED: In 2002 Carroll, a 19-year-old garbage collector, won the National Lottery prize. The Telegraph reported that he wouldn’t be celebrating at a pub—because the repeat offender was wearing a court-imposed electronic tag for a recent drunk-and-disorderly conviction. They also said he shouldn’t bother buying a new car—because his driving privileges had also been taken away. “Don’t tell me God doesn’t have a sense of humor,” a police officer told the paper. Carroll went on to become known as “The Lottery Lout” after alienating his neighbors by holding demolition derbies at his home in the middle of the night. In 2004 he was ordered to take drug tests after being caught with cocaine, and ended up with a five-month jail term—for not showing up for the drug tests. 

William “Bud” Post III of Pennsylvania

PRIZE: $16.2 million
WHAT HAPPENED: In 1988 Post had less than $3 to his name. He pawned a ring for $40 and gave it to his landlady to buy some state lottery tickets. When he won, he went on a legendary spending spree: He bought a car lot, a restaurant, a mansion, and an airplane (which he didn’t know how to fly). Within a few years, his wife had left him, his brother was arrested for hiring a hit man to kill him, and Post himself was arrested for firing a shotgun over the head of a bill collector. On top of that, his landlady sued him, saying that he’d promised her half of the winnings. She was awarded a third, but Post didn’t have it—he’d spent it all. He had to sell his house, and in 1992 auctioned off his 17 remaining lottery payments ($500,000 a year) for $2.65 million. He then proceeded to lose that sum in a series of business blunders and finally declared bankruptcy and lived the rest of his life on a $450-a-month disability check. He died in 2006 at the age of 66, having said, “I was much happier when I was broke,” and adding that he was sorry he had ever won the “Lottery of Death.”

Jody Lee Taylor of Collinsville, Virginia

PRIZE: $4.3 million
WHAT HAPPENED: In 1992 Taylor won the Virginia Lottery. Three years later he was arrested after having set fire to his girlfriend’s Ford Thunderbird and firing 15 shots from a .45-caliber pistol into the floor of their double-wide trailer. He was sentenced to a year in jail. Then in 2003 Taylor was spotted driving a brand-new pickup truck down Route 58 on the wrong side of the road…with his lights off…while naked. He refused to stop for police and during the chase tried to run down a deputy. His father later told reporters that he wished his son had never bought the lottery ticket. “Out of 10,000 people, there might be one who could handle the money,” he said. “The rest, it’ll push them over the edge.”