Ray William Johnson: True Story Podcast
This Lottery Winner Lost Everything - The Tonda Dickerson story
Thu, 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.
Chapter 1: What is the wildest lottery winner story?
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.
Chapter 2: Who is Tonda Dickerson?
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.
Chapter 3: How did Tonda win the lottery?
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.
Chapter 4: What were Tonda's plans after winning?
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?
Chapter 5: What legal issues did Tonda face?
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.
Chapter 6: What did the coworkers claim about the winnings?
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.
Chapter 7: How did Tonda's coworkers and Edward impact her case?
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.
Chapter 8: What was the outcome of Tonda's legal battle?
But in the meantime, she goes back to work at a different Waffle House while she waits on the appeal to go through. And around a year later, in the year 2000, the state Supreme Court reaches a decision, and they rule in Tonda's favor. And Tonda can't believe it. Finally, the lottery winnings are hers, and hers alone. She is gonna be rich!
Chapter 9: What happened after Tonda won her appeal?
Double until that same year, boom, Edward himself files a lawsuit against Tonda, claiming once again that he had intended for the winning ticket to go to all the servers at Waffle House, and also that he was promised the winner would buy him a white King Cab pickup truck. And because those promises were broken, he wants his winning lotto ticket back, which means he would get the full $10 million.
Chapter 10: Why did Edward file a lawsuit against Tonda?
Two years later, it's now 2002, and Edwards' lawsuit is still going on. And if that isn't bad enough, Tonda is in the middle of a divorce. And her former husband, the guy she's divorcing, is also claiming that he's entitled to half of Tonda's lottery winnings. And so she and her now ex-husband get divorced. And I don't know if she had to give him any of her winnings.
That's actually not public information that I have. But, lucky for Tonda, in Edward's lawsuit against her, the court actually dismisses the case. So his greedy ass isn't gonna get any money, nor is he getting that stupid-ass white truck he wants. So now, finally, Tonda can enjoy what's left of her winnings! She is gonna be rich! Triple until. Now here's where things get really crazy.
A few days after Edward's lawsuit against her gets dismissed, Tonda is over in Mississippi. And I have no idea why she's there, but her ex-husband is there. Not the ex-husband she just divorced, but a different ex-husband. We'll call him ex-husband two. And so she's there in her car and at some point, for some reason, Ex-husband 2 just snaps.
And boom, he jumps into her car and he pushes her into the passenger seat. And soon Ex-husband 2 is driving Tonda across the county. And he's yelling at her and he's threatening to unalive her if she doesn't agree to share her lottery winnings with him. Sometime later, they pull up to a boat launch. And he's still threatening her, saying she needs to hand over some of that money.
while Tonda is begging him to let her go. And then... Honda's cell phone rings and she's like, please let me answer it. And ex-husband two is like, nah. But the phone is in her purse and it keeps ringing. And she's like, if I don't answer this, people are going to start to worry and they're going to come looking for me. And so ex-husband two is like, I answer it.
And that is when she reaches into her purse and instead of grabbing her phone, boom, she grabs a .22 pistol she's got in there. And ex-husband two sees it and pow, he lunges at her and blam, she shoots him right in the chest. But he still grabs the pew-pew and he manages to wrestle it from her.
And Tonda, thinking on her feet, she's like, if I don't drive you to the hospital, you're going to die from that wound. And so he lets her take him to the hospital. And ultimately, he survives the gunshot. And she actually gets no charges for shooting him because, you know, he was trying to kidnap her.
Now, I don't know if he actually got charged for kidnapping her because there's literally no record of what happened to him anywhere that I can find. So I'll just assume that he was arrested and that they sent him to a federal butt sex prison. Regardless, now Tonda's still got some money left after all those court battles and legal fees. And nothing now is standing in her way.
She can finally enjoy it. She is finally gonna be rich. Quadruple until. Until Tonda decides to split her winnings with her family. And she transfers shares of her winnings to her family members. And this is when the IRS catches on. And the IRS is like, if you're sharing that money with your family, that counts as a gift. And gifts that large are actually subject to a gift tax.
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