When Waffle House waitress Tonda Dickerson was tipped a winning Florida lottery ticket in 1999, she thought she would never have to work again. Instead, her entire life was nearly ruined.
Winning the lottery sounds like a dream come true. For most people, getting that kind of money could change their life.
It certainly changed Tonda Dickerson’s life, but not for the better. After winning $10 million in the Florida lottery in 1999, Dickerson faced a saga of lawsuits, battled the IRS, and was briefly kidnapped by her ex-husband.
The ironic misfortune of Dickerson’s life post-lottery win isn’t an isolated incident. There are numerous examples of lottery winners falling on hard times, ruining their personal relationships, or even being killed.
While Dickerson’s circumstances weren’t quite as extreme as other past lottery winners, her story shows that even those who want to use their winnings responsibly can still end up in hot water after getting their prize.
How Tonda Dickerson Got Her Hands On A Winning Lottery Ticket
Bill Starling/Mobile Register/X (Formerly Twitter)Tonda Dickerson, pictured in April 1999, shortly after her lottery win.
In March 1999, Tonda Dickerson was working as a waitress at the Waffle House in Grand Bay, Alabama. One of the restaurant’s regulars, a man named Edward Seward, came in to eat breakfast on March 7th.
Seward tipped his waitress, Dickerson, with a Florida lottery ticket, something the man did regularly whenever he came in. Dickerson picked up the ticket and went on with her shift as usual.
Dickerson was in for the surprise of her life when that following Saturday, she found out that her ticket was the winner in the draw.
She had just won $10 million from the Florida lottery.
She was thrilled, assuming she would never have to work again. Rather than taking the entirety of the winnings all at once, Dickerson opted to receive smaller amounts of the prize money over the course of 30 years.
Dickerson wasn’t anticipating the lawsuits.
Tonda Dickerson’s Waffle House Coworkers Wanted To See Some Of The Winnings
Bo Nash/FlickrAn Alabama Waffle House (not the same one where Tonda Dickerson was employed).
As it turned out, Tonda Dickerson’s claim to the money wasn’t as straightforward as she thought. Edward Seward, who had gifted Dickerson the winning lottery ticket, would commonly tip servers with lottery tickets.
He did this so often, Dickerson’s coworkers alleged, that the colleagues had agreed to split any winnings amongst themselves if any of them got a prize. But Dickerson denied this, and so her coworkers took her to court.
In April 1999, her colleagues testified at the Mobile Circuit Court that they had all agreed, including Dickerson, to split any winnings from lottery tickets received as tips. There was even a couple who regularly ate at the same Waffle House who testified to hearing about this same agreement.
Though a jury decided against Dickerson, she wasn’t ready to give up yet. She turned down a settlement that would’ve allowed her to walk away with $3 million of the jackpot and put the court case behind her.
Instead, she opted to appeal to the Alabama Supreme Court.
This ended up being the right move for Dickerson, as the Alabama Supreme Court ruled to reverse the decision on Feb. 18, 2000. The court found that an agreement like the one allegedly made by the Waffle House employees couldn’t be enforceable under state law because it concerned gambling.
But that wouldn’t be the last time someone tried to sue Dickerson for her winnings. In 2002, about three years after Dickerson had won the $10 million lottery, the very man who gave her the winning ticket tried to sue her.
Seward claimed that Dickerson had not fulfilled her supposed promise that she would buy him a truck if she won the lottery. A Mobile County Circuit Judge threw out the case in February — but chillingly, that same week, Dickerson realized that an attempted lawsuit was the least of her worries.
Tonda Dickerson’s Kidnapping At The Hands Of Her Ex-Husband — And Her Battle With The IRS
Bill Starling/Mobile Register/InstagramTonda Dickerson, pictured during an interview about her winnings and court battles in 1999.
Back in 1997, just two years before she won the lottery, Tonda Dickerson had divorced her former husband Stacy Martin. Later on, the same exact week that Edward Seward’s case against Dickerson was thrown out in 2002, Martin made a reappearance in Dickerson’s life in an extremely violent way.
Martin attacked Dickerson while she was driving in Mississippi, and then forced her to drive toward an isolated area at Bayou Heron. During the drive, Martin threatened to kill Dickerson, especially when her phone rang.
He had apparently been tracking Dickerson, as he had just been released from jail after being linked to a December 2001 break-in at Dickerson’s home.
Once they arrived at Bayou Heron, Dickerson’s phone rang yet again.
“She asked him to let her answer it, saying that if she didn’t answer it, they would start looking for her,” a local sheriff reported at the time.
So, Martin let Dickerson pick up her phone. But instead of reaching for the phone, Dickerson cleverly reached for her handgun instead.
After Martin lunged toward her, Dickerson shot him in the chest, wounding him. Despite his injuries, Martin took the gun away from Dickerson, once again threatening to kill her. He also threatened to kill himself.
Somehow, Dickerson was able to convince Martin to go to the hospital instead, where he received treatment for his wound. The cops were called, and Dickerson was finally free after the terrifying abduction.
St. Petersburg Coastal and Marine Science CenterBayou Heron, the place where Tonda Dickerson narrowly avoided being murdered by her ex.
From there, the story gets murky. It doesn’t seem that Martin was ever charged with kidnapping, even though he was expected to be. However, he may have appeared in court in connection to the crime.
Meanwhile, Tonda Dickerson was also grappling with what would be a years-long battle with the IRS, regarding how much she owed them.
The IRS insisted that she needed to pay about $1 million in gift tax after she gave most of her winnings away to her family members via a business she set up. Dickerson’s fight against the IRS lasted at least until 2012.
The story once again gets murky, with some sources reporting that she lost in tax court and had to pay up, and others claiming her lawyers were able to successfully argue that the IRS was wrong to demand $1 million in gift tax.
Either way, Dickerson was able to walk away relatively unscathed, especially compared to some other unfortunate lottery winners like Urooj Khan, who was poisoned shortly after he learned about his prize, and Amanda Clayton, who died of a drug overdose less than a year after she collected her jackpot.
Little is known about Dickerson’s life today, but it’s believed that she currently works as a poker dealer at a casino in Biloxi, Mississippi.
Next, go inside the story of Stefan Mandel, the man who hacked the lottery and won 14 times. Then, learn about the tragic case of Jeffrey Dampier, who was murdered by his sister-in-law after winning the lottery.
