The Tragic Story of the Waitress Who Was Tipped a Winning Lottery Ticket
In 1999, a winning lottery ticket changed hands during a routine moment that barely stood out at the time. It was the kind of exchange people forget as soon as it happens. There was no celebration and no sense that anything important had just occurred. But that single moment slowly unraveled into years of consequences. Court cases followed, along with tax troubles and damaged relationships. What began as an ordinary interaction ultimately revealed how unexpected money can complicate lives in ways no one sees coming.
A Tip That Changed Everything
In March 1999, Tonda Dickerson, a waitress at a Waffle House in Grand Bay, was handed a Florida lottery ticket as a tip by a regular customer, Edward Seward. It was something he did often, a small gesture he picked up during long-haul trucking routes through Florida.
The next drawing took place the following Saturday. When the numbers were announced, Dickerson realized she was holding a winning ticket for the Florida Lottery’s $10 million jackpot.
She chose the annuity option rather than the lump sum, agreeing to receive $375,000 USD annually over 30 years. At the time, the decision seemed cautious and financially sound to her, especially being a woman in her late twenties raising a child and rebuilding her life after leaving an abusive marriage. With that, Dickerson probably believed the hardest part was over. It wasn’t.
Lawsuits From Familiar Faces
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Within weeks, four fellow Waffle House waitresses sued Dickerson, claiming there had been an informal agreement among staff to share any lottery winnings received as tips. They produced testimony from a couple who frequented the diner, stating they had heard Dickerson mention such an arrangement.
Dickerson denied that any agreement existed. A Mobile County jury initially sided with her coworkers, ruling against her in a decision reached in under an hour. She was offered a settlement that would have left her with roughly $3 million USD, but she refused and appealed.
In February 2000, the Alabama Supreme Court reversed the ruling. The court determined that any agreement tied to gambling proceeds was unenforceable under state law. Dickerson kept her winnings, but the legal stress did not end there.
Two years later, Seward himself filed suit, claiming Dickerson had promised to buy him a new truck if the ticket won. A judge dismissed the case, stating that a casual statement attached to a lottery tip did not create a binding obligation.
The dismissal brought temporary relief, but that same week marked a dangerous moment in Dickerson’s life.
A Kidnapping and a Fight to Survive
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Dickerson’s ex-husband, Stacy Martin, learned of her lottery payments and tracked her down in Mississippi. In February 2002, he forced his way into her vehicle and directed her toward a remote boat launch at Bayou Heron, threatening to kill her during the drive.
When Martin became distracted, Dickerson reached into her purse and pulled a .22-caliber handgun. As he lunged toward her, she fired, striking him in the chest. He survived the shooting and was taken to a hospital.
Law enforcement intervened, ending the abduction, but the incident left Dickerson traumatized. Even after surviving the kidnapping, Dickerson faced a prolonged dispute with the IRS. After distributing portions of her winnings to family members through a business arrangement, the agency sought nearly $1 million USD in gift taxes.
The case dragged on for years. In 2012, U.S. Tax Court ultimately ruled in her favor, determining that the IRS’s valuation of the gifted ticket was flawed. The ruling ended more than a decade of financial uncertainty tied directly to her win.
Life After the Spotlight
Unlike many lottery winners whose lives spiral after the attention fades, Dickerson eventually returned to a normal work routine. She later worked as a blackjack and poker dealer at a casino in Biloxi, Mississippi, while continuing to receive her annual lottery payments. The job gave her structure and a way to stay grounded outside the spotlight.
Her story is often grouped with other cautionary lottery tales, but it stands apart because of the scale of legal battles and personal fallout tied to a single tip left on a diner table.
Dickerson’s experience shows how sudden money can intensify existing tensions and invite new risks. The money itself was not the real issue. The attention that came with it was.