By the time she was driving her bleeding ex-husband to the hospital, Tonda Dickerson had already been sued by her co-workers, taken to court by a truck driver, and become Alabama’s most unlikely millionaire. And it all started with a single lottery ticket.

The year: 1999. The place: an ordinary diner in Grand Bay, Alabama, where a woman named Tonda Dickerson was working as a waitress. 

By the age of 28, Tonda had lived a life that could inspire a country song. She was a divorced single mother who had walked away from an abusive marriage with nothing but her determination and whatever she could fit into a suitcase. By 1999, she was working five shifts a week at the diner. It was barely enough to cover her bills, but it was steady work. 

That all changed on the morning that Edward Seward, a regular patron of the diner, tipped Tonda with a lottery ticket instead of cash. Technically, lotteries are not allowed in Alabama (due to state laws), but Edward was a long-haul trucker who made a habit of buying lottery tickets in other states and carrying them around with him. This particularly fateful lottery ticket had been bought in Florida. 

It was meant as a quirky gesture. No one – least of all Tonda – thought it would amount to anything. A week later, the winning numbers were announced, and Tonda’s ticket hit for $10 million. Just like that, the woman pouring coffee in a diner uniform became Alabama’s unlikeliest millionaire.

The unmistakable scent of opportunity

As you might imagine, winning the lottery is like ringing a dinner bell for opportunists. Within days, four of Tonda’s fellow waitresses lawyered up. They claimed there had been a pact between them that if any of them ever won from a customer’s ticket, they’d split it evenly. When Tonda disagreed, they took her to court. 

Tonda’s opposition even produced a witness in the form of a diner who swore she’d overheard Tonda talk about it right there in the restaurant. Tonda countered that the so-called “customer” was just a friend roped into the scheme, but the judge was unconvinced. The initial ruling went against Tonda, ordering her to share the winnings. But then an Alabama district court reversed it, noting that the agreement – being tied to gambling – wasn’t enforceable under state law.

Next in line was Edward Seward, the trucker who’d tipped her the ticket. When he learned that she’d won, he called up a lawyer of his own. His argument was that Tonda had supposedly promised to buy him a new truck if she won – and he was keen to collect on that promise.

Here’s where a bit of legal jargon called promissory estoppel comes in, which dictates that you can be held to an oral promise if a court decides it was reasonable for the other party to rely on it. But this particular court didn’t buy it. Statistically, a lottery ticket is worth less than the paper it’s printed on. No reasonable person, they decided, could expect a multi-million-dollar return, much less from a ticket they had willingly given away. Hence, Seward’s case was tossed out and his hopes of cashing in on Tonda’s win were erased.

If you can believe it, things got worse from there

Not long after the win, Tonda’s abusive ex-husband found out about her windfall. One afternoon, he appeared outside her home without warning and forced her into his car. He drove in silence at first, heading out of town toward a remote part of rural Alabama. When he finally spoke, it was to tell her he planned to kill her and take the money for himself.

About 20 minutes into the drive, his phone rang. While he was distracted, Tonda reached into her purse for the gun she’d started carrying after their divorce. She aimed it at him. He lunged across the seat to try and take it from her, and in the struggle she fired, hitting him in the chest.

Miraculously, he didn’t die. In a twist that is a testament to her character, Tonda urged him to get medical help, even switching seats with him so she could drive him to the hospital herself. He survived, served a short prison sentence for the kidnapping, and she walked away alive (and still rich).

Not a fix-all after all

Tonda’s story is dramatic, but sadly not unique. In fact, financial advisors have been warning for years that winning the lottery often brings more problems than solutions.

Statistics show that lottery winners are significantly more likely to declare bankruptcy than the average member of society. The windfall often draws out estranged relatives, manipulative friends, and – in some cases – outright criminals. Add to that the fact that most people are not financially disciplined or skilled enough to know how to handle a sudden influx of money, and you’ve got a recipe for disaster. 

Just ask:

• Amanda Clayton, who won $1 million, kept claiming food stamps, was convicted of welfare fraud, and died of an overdose within a year.
  
• Michael Carroll, who blew £10 million on drugs, sex workers, and building a demolition derby in his backyard.
  
• William Post, who won $16.2 million in 1988, was sued by his ex, and had his own brother try to hire a hitman to kill him. He died broke and estranged from his family.

When money appears overnight, it doesn’t just change your bank balance – the sad reality is that it changes the people around you – and not always for the better. Or perhaps it just reveals them?

Take a lesson from Tonda

Despite the rollercoaster ride that followed after her win, Tonda remained level-headed enough to make some very smart decisions. 

Firstly, she declined a lump-sum payout of her winnings and requested 30 annual payments instead. This meant that she would be less inclined to burn through the cash all at once, and that her millions would continue to sustain her for the next three decades of her life.

Then, she went back to work – not at the diner, but at a casino, where she was employed as a blackjack and poker dealer. It wasn’t glamorous work, but it kept her in a steady routine (which meant she didn’t spend every day lying on her couch flipping though catalogues) and most importantly, it meant that she kept earning an income instead of living off her millions.

I can only imagine that working in a casino and seeing people lose money through reckless decisions daily is somewhat of a spending deterrent as well.

Despite a little bit of IRS-related drama (she was sued by the American equivalent of SARS for not paying gift tax, and ended up having to pay about $700,000), Tonda’s life looks very ordinary these days. She goes to work, hangs out with her family and friends and collects her lottery cheque annually like it’s no big deal.

Stories like Tonda’s captivate us because they’re part fairy tale, part cautionary tale. We imagine the champagne cork popping, the debt-free life, the dream house. But we also know deep down that sudden wealth doesn’t erase old problems. In fact, it often magnifies them.

Lottery hopefuls, take note: a lottery win can be salvation or destruction, and sometimes, it’s both in the same year.

About the author: Dominique Olivier

Dominique Olivier is the founder of human.writer, where she uses her love of storytelling and ideation to help brands solve problems.

She is a weekly columnist in Ghost Mail and collaborates with The Finance Ghost on Ghost Mail Weekender, a Sunday publication designed to help you be more interesting. She now also writes a regular column for Daily Maverick.

Dominique can be reached on LinkedIn here.