In the spring of 1999, Tonda Dickerson, a Waffle House waitress in Grand Bay, Alabama, saw her world transformed when a regular customer slid her what seemed like a whimsical tip—a Florida lottery ticket. That ticket turned out to be the golden one, worth a staggering $10 million. But the dream-come-true that many fantasize about quickly spiraled into a decade-long saga of lawsuits, betrayal, violence, and relentless scrutiny from the IRS. What followed was not a fairy tale, but a cautionary epic of what happens when life-changing fortune collides with human expectation, legal ambiguity, and greed.
A “Tip” Worth Millions
The ticket came from Edward Seward, a longtime customer of the Waffle House where Tonda worked. Known to leave lottery tickets as tips for his favorite waitstaff, Seward handed over the ticket as part of a casual exchange. But when it turned out to be a $10 million jackpot, it wasn’t just a stroke of luck—it became a legal battleground.
Tonda opted for the annuity payout, receiving $375,000 per year for 30 years. She made what she believed were sensible financial decisions, including setting up a corporation called “9 Mill, Inc.” to hold her winnings. But those steps couldn’t protect her from the tidal wave of consequences that followed.
The Coworker Lawsuit: From Friendship to Legal War
Almost immediately, Tonda’s coworkers sued her, claiming that they had all made a verbal pact to split any lottery ticket tips. They argued the agreement was mutual and that she had reneged on her promise once the money came in.
In court, their argument initially prevailed—she lost the case. But Tonda appealed, and the case eventually reached the Alabama Supreme Court, which reversed the decision. The justices ruled that any verbal agreement to share lottery winnings constituted a form of illegal gambling, thereby rendering the agreement unenforceable.
Though the ruling cleared her of legal responsibility, it cost her emotionally. What started as camaraderie among service workers had devolved into bitterness and betrayal. Tonda had gone from serving hashbrowns to standing alone in courtrooms.
The Tipper Turns Litigious
Tonda’s troubles didn’t end there. Edward Seward, the customer who had gifted her the ticket, also came forward with claims. He alleged that Tonda had promised to buy him a truck in return for the winning ticket. When she didn’t, he took her to court.
Once again, the lawsuit was dismissed. The courts deemed the claim baseless—there had been no legal agreement, no contract, no grounds to uphold Seward’s expectations. Still, the public spectacle of the lawsuit deepened Tonda’s entanglement in a story that was starting to sound more like a movie script than real life.
A Violent Attack by Her Ex-Husband
If lawsuits weren’t enough, in 2002, the situation took a shocking and dangerous turn. Tonda’s ex-husband attempted to kidnap and kill her in what appeared to be a targeted attack motivated by her winnings.
During the ordeal, Tonda managed to shoot him with a .22 pistol in an act of self-defense. She survived the attack, but the incident revealed the escalating personal cost of her newfound wealth. She had become, in essence, a target—not just of lawsuits and financial claims, but of physical violence.
A Decade-Long Battle with the IRS
Perhaps the most enduring conflict Tonda faced came not from coworkers, acquaintances, or ex-lovers—but from the Internal Revenue Service. The federal tax authority claimed that when she formed her corporation to distribute shares to family members, she had inadvertently made a taxable gift of millions of dollars.
For more than a decade, the IRS fought her, asserting that she owed over $1 million in gift taxes. The litigation wore on, moving through the complexities of tax law and corporate structuring. But Tonda stood firm, and in the end, the tax court ruled in her favor.
It was a vindication that came after years of stress, legal bills, and public scrutiny. But for Tonda, the victory was likely a pyrrhic one—won at great personal cost.
More Curse Than Blessing
Tonda Dickerson’s story is a parable of modern-day fortune—a potent reminder that sudden wealth, particularly of the lottery kind, can come with a hidden price tag. Her windfall launched her not into luxury and peace, but into courtrooms, police interviews, and IRS audits.
The dreams of early retirement, travel, or carefree living that many associate with winning the lottery were overshadowed by battles for her reputation, her safety, and her sanity. Despite surviving lawsuits, threats, and an assassination attempt by someone she once trusted, Tonda remained largely out of the limelight in later years, likely by design.
The Myth of the Lottery Dream
At its core, Tonda’s experience challenges the popular myth that wealth solves all problems. In reality, her sudden financial gain amplified existing tensions and created new enemies. She didn’t change—the people around her did.
Legal experts have cited her case as a classic example of why lottery winnings should be handled with extreme caution—ideally with airtight legal advice and privacy. Tonda’s case has even been taught in law schools as an example of verbal contracts, illegal gambling claims, and tax implications surrounding unexpected wealth.
In the End, Survival Over Splendor
Two decades after her win, Tonda Dickerson’s name remains a haunting cautionary tale in the annals of lottery lore. She survived lawsuits, an attempted murder, and a relentless IRS campaign—all for a ticket handed over during a breakfast shift.
To some, she is a tragic figure; to others, a survivor. Either way, her story is a reminder that fortune can sometimes invite misfortune, and that not all windfalls come with a silver lining.
In a world obsessed with rags-to-riches stories, Tonda Dickerson’s tale is a rare one: a real-life example of how winning the lottery can make you rich—but cost you everything else.