Nadine Purdy

Many people dream of winning the lottery or striking it rich, but in reality, 70 percent of people who become instantly wealthy squander their money away within a few years.

Nadine grew up poor in Greenwich, Connecticut. At the age of 19, she packed her bags and moved to New York City to pursue her dream of becoming a fashion designer. Nadine started by selling scarves at street fairs and flea markets, and within a few months, she had accumulated more than $60,000 in cash.

This small-town girl's dreams started to become more of a reality after she got married and opened Yoshi, a trendy clothing boutique in New York's SoHo neighborhood.

Within six months, Yoshi was becoming one of the hippest stores in the city and had become quite profitable. Their first year of sales topped $1.2 million, and during their best year, Nadine says they made $2.2 million. "It was amazing how much cash was coming in and also how fast we were spending it," Nadine says.

Nadine and her husband started hanging out with an elite crowd. She says they took extravagant vacations, even paying $500,000 in cash for a new condo, and spending about $1,000 a week in New York's finest restaurants. "I felt like I had arrived," Nadine says. "At the time, it was my dream life."
Once rich Nadine Purdy and Oprah

Nadine, her husband and their three children were living in a beautiful home and enjoying the success of their small boutique...until Nadine's life took a sudden turn.

"I hung out with the beautiful people, and I felt very inadequate," Nadine says. "Like I wasn't up to their the people were going to find out I was a fraud."

That's when Nadine decided to start using drugs. "Cocaine gave me a feeling of strength," she says. "It was a really good feeling in the beginning."

Nadine became a cocaine addict and, she says, developed a $600-a-day habit. She estimates that she spent about $250,000 in one year on drugs. Nadine's husband divorced her and she lost custody of their children.

After the divorce, Nadine says, she began abusing heroin and ended up homeless, sleeping on the street and in subway tunnels. "One of my lowest points was being homeless and living in the New York City subway system in the tunnels and not being able to see my children," she says.
Once rich Nadine Purdy and Oprah

After stints in rehab and in prison, Nadine says she did a lot of work on herself and realized she had been trying to fill a hole in her heart with material things. She says she thought she needed the fancy car, the clothes and the trips to make her happy. "[I didn't realize] that man makes the money, money doesn't make the man," she says.

Since then, Nadine has been picking up the pieces and rebuilding her life. She's been clean for five and a half years. "It was a long, rough road," she says.

She's currently running three clothing boutiques with her sister. The stores are called Purdy Girl, and Nadine does the buying for all three locations. She's also living in an apartment with her children and managing her finances.

"I don't have a lot of extra. I pay my bills, [but] it's tough," she says. "I wouldn't mind having the money that I had back then, but I definitely don't want the lifestyle. I'm so much happier with the way that I am now."
Amy and Tom

Amy and Tom were working full time and living paycheck to paycheck when a quick trip to a convenience store changed their lives forever.

One night, Amy ran out to the store to buy a gallon of milk, but returned with a lottery ticket instead. "I thought, 'I'm just going to buy some lottery tickets and see what happens,'" she remembers.

That same evening, Amy called the lottery office to check her numbers...and found out she was the big winner! The roll of quarters Amy brought to the store had suddenly grown into $15.5 million. "It's an unbelievable feeling to win that much money," she says. "I thought, 'I'm set for life.'"

Amy quit her job driving buses and Tom quit his job building cabinets, and the new millionaires began spending their winnings. The money, paid out annually over a 20-year period, totaled $487,000 per year after taxes.

The couple bought a big new house and took expensive trips to Ireland, Alaska, Cancun and Hawaii. "We just bought whatever we wanted," Amy says. "It's amazing how fast that money can go."

As Amy and Tom started enjoying their new lifestyle, friends and family began asking them for loans. Amy estimates she's given away almost a million dollars over the years. "I've been hurt many times by people that I thought were friends," she says. "I just have a problem with saying no."


Amy and Tom eventually moved to another town where nobody knew of their windfall. Sometimes, Amy says, she regrets winning the lottery.

"A lot of my friends from New York, I do not speak to anymore," Amy says. "I do wish that I bought the milk sometimes because I wouldn't have half the headaches that I have [now]."

Although Amy says the money hasn't changed her, she thinks it's changed the people around her. "I wish I was poor old Amy back in New York where everybody just liked me for me, and they didn't look at me with dollar signs in their eyes," she says.

If Amy could go back and do things differently, she says she never would have gone public with her winnings. "I wish I wouldn't have done the media thing. [I should have] kept [the news] to myself."


Elizabeth, a stay-at-home mother, will receive $1.3 million to be paid to her over time after a lawsuit stemming from her father's death. Of the $260,000 she's received so far in two years, Elizabeth says she has just $18,000 left.

"I just never felt any pride in it," she says. "There was so much grief and emotion that went with the situation that I just let it go."
Wayne Powers, Ted Rodrigue and Oprah


In a controversial Showtime documentary, Reversal of Fortune by filmmaker Wayne Powers, cameras follow Ted Rodrigue, a 45-year-old who has been periodically homeless for the last 20 years. Wayne tells Ted his film is about what's it's like to be homeless, but there's more planned for Ted's story on film.

One day, Ted headed for the dumpster to search for bottles and cans, which he recycled for money. There he found a briefcase containing $100,000 in cash—placed there by Wayne.

"There [were] a lot of emotions all at once," Ted says about finding the briefcase. "I thought I was going to get shot. I thought it was drug money. Then I thought it was a prop for the movie, and I would have to give it back. It didn't sink in for a good half an hour—then I knew [it was mine to keep]."
Ted Rodrigue


Wayne says he was inspired to make Reversal of Fortune because of his daily interactions with homeless people in Los Angeles. "I thought to myself, 'What would happen if I actually was able to give someone $100,000 and the free will to do with it what they wanted to do?'" he says. "Would that turn their life around or would it create more problems?"

He says they searched extensively to find a subject like Ted before filming began. "We picked somebody who was able to pass a medical exam, a psychiatric evaluation, a drug test. When he did receive the money, I actually for the first time felt quite optimistic," Wayne says. "Ted had talked about wanting to get a one-bedroom apartment, a job, he was so happy. And I thought, 'Wow, this is really great. Because of me and someone else's money maybe this will really turn his life around.'"

While Ted received financial counseling to deal with his influx of money, his old habits died hard. Ted got a room but continued to sleep on the floor. He still collected cans and bottles, the primary way he'd survived for years. Ted also spread his wealth around—he says he paid off friends' debt, bought a friend a new car and himself a truck that cost $34,084.89. He also got married.

"You never think...the money's going to run out sooner or later," Ted says. "At the time I was living in L.A., and I thought with having that money, I could go back to Sacramento and reunite with my family, and that it would change everything. It did for a while—I had more friends than I could count."
Wayne Powers and Ted Rodrigue


Ted says he not only spent or gave away all $100,000, he actually owes more money now than he did before. "I thought it would erase all my problems. I thought I would never be homeless again," he says. "But, like I said, I made a couple of bad choices."

Ted says some of those bad choices include his expensive truck, getting his teeth fixed, giving so much money away, turning down various job offers, and his marriage—which ended, he says, when his wife left him as soon as the cash ran out.

"It was a frustrating process, in a way, because I think that there were a lot of opportunities sent Ted's way," Wayne says. "And while you're with someone, and the closer you get to them, and the more that you kind of root for them and understand them, the more frustrating it gets when those opportunities are passed by. I think that it shows that, from a personal story, people that are homeless, there are certain demons inside them. ... I think alcoholism plays a part of that. I learned that in providing somebody with the necessities to be able to turn their life around, a car, a telephone, a roof above their head, a driver's license, all the things that we hear is what somebody needs to be able to turn their life around, it still, unfortunately, in this particular case, was not enough."

Back living on the street, Ted says, "I'm not happy, but I'm contented."
Financial expert Lynnette Khalfani


While you're unlikely to ever see a windfall on the magnitude of Nadine, Amy, Ted or Elizabeth's, you probably will get a tax refund or year-end bonus. According to Lynnette Khalfani, financial expert and author of The Money Coach's Guide to Your First Million rather than simply using this money to treat yourself, you should instead use it to pay off your debts.

Lynnette says that many people think they "deserve" to treat themselves. "And of course you deserve it," Lynnette says. "But you also deserve to keep it in the family and to have financial stability. You don't want to have to lament over your losses and really feel bad about the fact that you blew the money."

If you should be so lucky as to get a windfall of $50,000 or more, Lynnette says there are five things you should do to make sure you keep it.

  • Get financial help. A trusted advisor can talk to you about long-term plans and help you set a budget.
  • Make sure you have a system in place for dealing with requests for money. This can be someone like an accountant, who can handle the requests so you don't have to feel emotionally responsible saying no.
  • Make sure you have a structured way of giving—like to charities or to your church—so no one can make you feel guilty for not giving to them individually.
  • Plan before you invest. Don't make any big moves without a long-term strategy.
  • Give yourself time. Though you may want to, don't make rash moves right after getting your money.