Ray William Johnson: True Story Podcast
This Lottery Winner Lost Everything - The Tonda Dickerson story
05 Jun 2025
In 1999, Tonda Dickerson, a waitress at a Waffle House in Grand Bay, Alabama, received a Florida lottery ticket as a tip from a regular customer, Edward Seward. To her astonishment, the ticket turned out to be a $10 million winner. Dickerson's windfall quickly became a legal quagmire. Her coworkers sued, claiming a verbal agreement to share any lottery winnings, but the Alabama Supreme Court ruled such agreements unenforceable due to the state's gambling laws. Seward also sued.
Full Episode
So this has to be the wildest lottery winner story I've ever heard. And it all starts with this woman. Her name's Tonda. And Tonda's in her late 20s, living in Alabama, and she's working as a server at the local Waffle House, barely making enough money to get by. But one day in 1999, her whole life changes. Because she's at work serving food and whatnot, and a customer walks in.
This truck driver, Edward. And Edward eats at this Waffle House a lot. And on this particular day, Tonda is his server. And when he's done eating, he tips her with a lottery ticket, which he often tips the servers there with lottery tickets. But the next day, the lottery numbers are announced. And one after another, Tonda's ticket starts to match.
And suddenly, boom, all the numbers match, and Tonda has officially won the lottery. $10 million, which adjusted for inflation would be about $19 million today. So this amount of money is a life-changing amount of money for anyone, but especially for Tonda. So immediately she quits her job at the Waffle House. And she starts making plans for this money.
She decides to receive it in payments of $375,000 a year over 30 years, rather than getting the lump sum all at once. She plans to build a new house. She plans to replace her car with a new car. I mean, this is huge for her. $10 million is going to set her up forever. She's going to be rich.
Until... A few days later, Tonda shows up to the lottery headquarters to sign some paperwork and collect some of her winnings. And the people working there are suddenly like, nah bro, she can't have the money. Why?
Well, because at the Waffle House Tonda worked at, all the waitstaff there claimed that they all had some long-standing agreement that if one of them won the lottery from Edward's ticket study tips, that they would split the winnings amongst them. And so four of Tonda's co-workers who had been working that day, they feel like they deserve a piece of that $10 million.
And so they went and hired lawyers. And the lawyers contacted the lottery commission and they stopped them from paying out Tonda until the dispute can be resolved. And Tonda's like, what? I didn't agree to split the winnings. And so, boom, her four former Waffle House coworkers file a lawsuit against her. And so eventually they all go to court and the four coworkers all testify against Tonda.
And they even bring in Edward as a witness. And Edward testifies against Tonda too, claiming that he intended for the winning ticket to go to all the waitstaff there, not just Tonda. And he also claims that he was promised that the winner would buy him a white King Cab pickup truck. And so the trial goes on for a while, and at the end of it all, Tonda actually... Loses.
The jury believes the Waffle House co-workers. And the judge orders that Tonda take the lump sum payment of winnings and split the money with the other four Waffle House servers. And of course Tonda is pissed off and she feels like she won that money fair and square. And so she appeals the court's decision.
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