Sean Kernan
Waitress Wins $10M Lottery—And Complete Chaos Unfolds
The true story of Tonda Dickerson.
Sean Kernan·Sean Kernan
Fri, April 4, 2025 at 4:34 PM CDT·
It all began in a dying Alabama town.
The Grand Bay Waffle House was packed with regulars. Most were blue-collar folks or retirees, drawn in by the promise of hot coffee and comfort food. The kitchen buzzed with activity. The smell of frying bacon wafted through the air.
Edward Seward sat alone at his table. He was a long-time truck driver and customer. The waitresses all knew him by name and, today, his waitress was Tonda Dickerson.
Tonda was in her late 20s and had lived a hard life up until now. She was a divorced single mother. She left her abusive husband only a few years prior. She scraped by, juggling five shifts a week just to keep the lights on.
When Seward wrapped up his meal, he handed Tonda a tip that was anything but ordinary. It was a Florida lottery ticket he’d picked up on the road.
This kicked off a series of events that would make for a great movie script.
The following week, the winning lottery number was announced. Tonda was stunned to learn her life was about to change: she had just won over $10 million.
Unlike most lottery winners, she chose to take 30 annual payments of $375K rather than a lump payment of $4 million. Because she was still young enough to enjoy the payments, and this offered badly needed stability. It also helped prevent her from immediately spending all the money (statistically, lottery winners are much more likely to declare bankruptcy than the average American).
She abruptly quit her job at the Wafflehouse — for the time being.
Then things went south
First, four other waitresses took Tonda to court. They claimed they all had a deal to share any lottery winnings from tickets left by customers.
They even brought in a diner who testified that Tonda talked about the agreement right there in the restaurant.
Tonda fired back, saying the woman wasn’t a real customer at all—just a friend they brought in to sway the case.
The initial ruling went against Tonda, ordering her to split the money. But then an Alabama district court stepped in and reversed it, saying the supposed agreement was tied to gambling—and thus wasn't a valid deal under local laws.
Tonda’s lawyer didn’t mince words, describing the coworkers as, “Rats coming out of the woodwork.”
One would think this was a moment of relief for Tonda. Sadly, it was only the start of her problems.
Her Wafflehouse customer, Edward Seward, found out Tonda won the lottery and was far from thrilled. He called a lawyer and sued for his share of the money. He claimed Tonda said, “I’ll buy you a new truck if I win with this ticket.”
There’s a pesky legal concept called promissory estoppel, where you can be held accountable for an oral promise — if the court sees it as reasonable and justified.
Seward's problem was that tipping someone a lottery ticket is, statistically, a very low value tip. In the rare chance they win, you can’t reasonably expect a partial return of a huge fortune.
Put another way, you wouldn't tip cash, and then expect the cash back if some specific event happens in the future. Hypotheticals don't hold up well in court.
His case was quickly rejected.
Things go from bad to worse
Tonda’s abusive ex learned she’d won the lottery. He shows up and kidnaps her, keeping her at the wheel and forcing her to drive.
He found her, forced her into a car, and made her drive—saying he was going to kill her. He directed her toward a remote stretch deep in rural Alabama. About twenty minutes into the drive, he answered a call. While he was distracted, Tonda made her move. She pulled out a gun and pointed it at him.
He lunged for it—and before he grabbed it—Tonda pulled the trigger, shooting him in the chest.
He managed to snatch the gun away from her. In a testament to Tonda's character, she urged him to go to the hospital. They went and he was treated. He survived. But was sentenced to a brief stint in prison.
Tonda’s story, though dramatic, has many parallels to other lottery winners. In so many cases, winners report friends and long lost family turning up out of the woodwork, trying to get a piece of the money. Many, many families have been torn apart because of a jackpot. The lottery turns people into parasites. The curse is real.
The sad history of former lottery winners
One man invested $3M in a meth ring and, unsurprisingly, lost all of his money.
Amanda Clayton was found dead of a drug overdose little more than a year after winning $1M. She also kept taking food stamps despite winning and was convicted of welfare fraud. Her winnings created a downward spiral of addiction that ruined her life.
Michael Carroll won $12 million and spent all the money on sex workers, drugs, and constructing destruction derby ring in his backyard.
Another man, William Post had a similar experience to Tonda. After winning $16.2m in the Pennsylvania lottery in 1988, his ex-girlfriend sued him for part of the winnings. If that wasn't enough, his brother was convicted of attempting to hire a hitman to kill him.
He eventually died broke and estranged from much of his family.
The conclusion to Tonda’s story
Fortunately, Tonda's story had a little more good fortune than other winners. She settled a lawsuit with the IRS over her winnings (she'd been sued over a gift tax that was owed, because the ticket was given to her).
FYI: The IRS investigates 100% of big lottery winnings. Plan on hearing from them if you strike it rich as it is part of their mandatory audits. Tonda also did what most lottery winners should: she went back to working a day job, maintaining a schedule and income rather than having endless free-time to spend.
Reflecting on the chaos
In writing this article, I studied dozens of lottery winners. The happiest and healthiest winners were the ones who stayed busy and maintained some type of employment. It's as the saying goes, "Idle time is the devil's playground."
Today? Tonda deals blackjack and poker tables at a casino and still gets her annual lottery check. And most fortunately, she didn't lose her life to a maniacal ex. And she still has a happy relationship with her family.
As a former financial analyst and budget manager, it pained me reading so many cases of people squandering millions on petty expenses and whims. But the breakdown of families appears to be the worst part of the lottery curse.
If I ever win a Mega Millions jackpot, three things will happen:
I will call my lawyer.
I will call my accountant.
And I won't tell a soul I won the money.
https://currently.att.yahoo.com/creator ... 25577.html
Lotteries
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swamidada786
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Re: Lotteries
Texas woman sues state lottery after not receiving controversial $83.5M jackpot
Michelle Watson, CNN
Sat, May 24, 2025 at 6:33 PM CDT·
A woman in Texas is suing the state’s Lottery Commission for not paying out an $83.5 million award, more than three months after the numbers on her ticket matched the winning numbers in a drawing, according to court documents obtained by CNN.
“Every Texan knows what that should mean when it comes to the lottery – if you win, you should get paid,” the suit says. “It shouldn’t take a lawsuit to get paid when you win the lottery. But that’s exactly what has happened here.”
The woman bought her ticket through a lottery courier service, firms which allow customers to purchase tickets virtually, using a mobile app or other online interface.
The woman, identified only as Jane Doe in the suit, purchased a ticket for the “Lotto Texas” lottery game through an app called Jackpocket on February 17, and her numbers matched those of the numbers pulled at 10:12 p.m. CT the same day, according to the lawsuit.
A week after Doe won her ticket, then-Texas Lottery Commission Executive Director Ryan Mindell announced a move to ban courier services like the one Doe used, under Texas law. The ban became effective on May 19, according to a lottery commission spokesperson. Mindell resigned in April.
“We all know the Commission is not allowed to change the rules after the drawing. But the Commission has apparently tried to do so and relied—at least in part—on this ex post facto announcement to continue to refuse to pay Plaintiff her lottery winnings simply because she utilized a lottery ticket courier service to buy the winning ticket,” the lawsuit says.
A spokesperson told CNN in an email Saturday the commission “does not comment on pending litigation.”
The lawsuit also alleges Doe’s unpaid winnings could be used to pay other Texas Lottery winners, or may be reallocated and redirected to “other Commission liabilities or purposes,” potentially reducing the amount owed to her.
Attorneys for the woman have also filed for a temporary restraining order and requested for a temporary injunction to stop Acting Deputy Executive Director of the Texas Lottery Commission Sergio Rey from doling out funds, which the lawsuit alleges Doe still has not received.
“If Mr. Rey is not restrained and enjoined from disbursing or diminishing the Plaintiff’s jackpot prize winnings, Plaintiff will suffer damages that will be incapable of being measured by any certain pecuniary standard before notice is given and a hearing is held on Plaintiff’s Application for Temporary Injunction,” a court document said.
CNN has reached out to Texas Gov. Greg Abbott’s office, Jackpocket, and Rey for comment.
What is a lottery courier service?
A lottery courier service acts as a third-party vendor that buys lottery tickets on behalf of customers, coordinates the purchase of physical tickets through brick and mortar stores the services often own, and notifies buyers if they win.
Courier services are typically operated online or through an app, offering a convenient way to play games. Some couriers even offer national lottery games like Mega Millions and Powerball.
Lottery couriers, which had been operating in Texas since 2019, became a focus in April 2023 after a single entity bought 25 million lottery tickets in less than 72 hours using a courier service, CNN affiliate WFAA reported.
The entity purchased “nearly every possible number combination,” the release from the governor’s office said at the time. The investor doubled its money because the jackpot was so high, and the winner took home $57.8 million before taxes, WFAA said.
Courier services are operating in 19 states, according to a report published in 2024 by the Florida Office of Program Policy Analysis and Government Accountability.
Only three states – New York, New Jersey and Arkansas – regulate the courier service industry, according to a 2024 Texas House report. Without such regulations in Texas, couriers are not required to obtain a license or permission from the Texas Lottery to operate, the report found.
Purchasing via a lottery courier has two advantages for the customer, said Victor Matheson, professor of economics at College of the Holy Cross.
“It allows the buyer to conveniently buy tickets without having to go to a regular lottery retailer and it also potentially allows out-of-state buyers to purchase tickets in any lottery across the country,” Matheson said in February.
The service can have drawbacks like a fee, legality issues and lack of a limit to how many tickets are purchased, Matheson added. Other legal concerns include the regulation of sales across state lines when each state controls its own lottery games, sales to underage players, ticket buying syndicates and other issues.
https://currently.att.yahoo.com/news/te ... 34905.html
Michelle Watson, CNN
Sat, May 24, 2025 at 6:33 PM CDT·
A woman in Texas is suing the state’s Lottery Commission for not paying out an $83.5 million award, more than three months after the numbers on her ticket matched the winning numbers in a drawing, according to court documents obtained by CNN.
“Every Texan knows what that should mean when it comes to the lottery – if you win, you should get paid,” the suit says. “It shouldn’t take a lawsuit to get paid when you win the lottery. But that’s exactly what has happened here.”
The woman bought her ticket through a lottery courier service, firms which allow customers to purchase tickets virtually, using a mobile app or other online interface.
The woman, identified only as Jane Doe in the suit, purchased a ticket for the “Lotto Texas” lottery game through an app called Jackpocket on February 17, and her numbers matched those of the numbers pulled at 10:12 p.m. CT the same day, according to the lawsuit.
A week after Doe won her ticket, then-Texas Lottery Commission Executive Director Ryan Mindell announced a move to ban courier services like the one Doe used, under Texas law. The ban became effective on May 19, according to a lottery commission spokesperson. Mindell resigned in April.
“We all know the Commission is not allowed to change the rules after the drawing. But the Commission has apparently tried to do so and relied—at least in part—on this ex post facto announcement to continue to refuse to pay Plaintiff her lottery winnings simply because she utilized a lottery ticket courier service to buy the winning ticket,” the lawsuit says.
A spokesperson told CNN in an email Saturday the commission “does not comment on pending litigation.”
The lawsuit also alleges Doe’s unpaid winnings could be used to pay other Texas Lottery winners, or may be reallocated and redirected to “other Commission liabilities or purposes,” potentially reducing the amount owed to her.
Attorneys for the woman have also filed for a temporary restraining order and requested for a temporary injunction to stop Acting Deputy Executive Director of the Texas Lottery Commission Sergio Rey from doling out funds, which the lawsuit alleges Doe still has not received.
“If Mr. Rey is not restrained and enjoined from disbursing or diminishing the Plaintiff’s jackpot prize winnings, Plaintiff will suffer damages that will be incapable of being measured by any certain pecuniary standard before notice is given and a hearing is held on Plaintiff’s Application for Temporary Injunction,” a court document said.
CNN has reached out to Texas Gov. Greg Abbott’s office, Jackpocket, and Rey for comment.
What is a lottery courier service?
A lottery courier service acts as a third-party vendor that buys lottery tickets on behalf of customers, coordinates the purchase of physical tickets through brick and mortar stores the services often own, and notifies buyers if they win.
Courier services are typically operated online or through an app, offering a convenient way to play games. Some couriers even offer national lottery games like Mega Millions and Powerball.
Lottery couriers, which had been operating in Texas since 2019, became a focus in April 2023 after a single entity bought 25 million lottery tickets in less than 72 hours using a courier service, CNN affiliate WFAA reported.
The entity purchased “nearly every possible number combination,” the release from the governor’s office said at the time. The investor doubled its money because the jackpot was so high, and the winner took home $57.8 million before taxes, WFAA said.
Courier services are operating in 19 states, according to a report published in 2024 by the Florida Office of Program Policy Analysis and Government Accountability.
Only three states – New York, New Jersey and Arkansas – regulate the courier service industry, according to a 2024 Texas House report. Without such regulations in Texas, couriers are not required to obtain a license or permission from the Texas Lottery to operate, the report found.
Purchasing via a lottery courier has two advantages for the customer, said Victor Matheson, professor of economics at College of the Holy Cross.
“It allows the buyer to conveniently buy tickets without having to go to a regular lottery retailer and it also potentially allows out-of-state buyers to purchase tickets in any lottery across the country,” Matheson said in February.
The service can have drawbacks like a fee, legality issues and lack of a limit to how many tickets are purchased, Matheson added. Other legal concerns include the regulation of sales across state lines when each state controls its own lottery games, sales to underage players, ticket buying syndicates and other issues.
https://currently.att.yahoo.com/news/te ... 34905.html
Re: Lotteries
‘The odds are astronomical’: Canadian man wins lottery jackpots four times
Cancer survivor David Serkin won draws in August, November and May, and another more than a decade ago
Ramon Antonio Vargas
Wed 11 Jun 2025 10.00 BST
Share
How do you say “lottery winner” in western Canada? The answer is: David Serkin, the name of the cancer survivor from Alberta who won three separate lottery jackpots between August and May to accumulate about $2.5m in prize money.
According to officials, those lucky tickets marked the second, third and fourth times Serkin had won a lottery in his life, a feat that he had vanishingly small chances of pulling off and gained notice on corners of the internet dedicated to charming news stories.
“I know the odds are astronomical, [and] I don’t think it’ll happen again,” Serkin said in a press bulletin issued recently by the Western Canada Lottery Corporation (WCLC). “But I still like buying tickets.”
Serkin won draws of $500,000 on 20 August, $1m on 16 November and $1m on 3 May, the last of those coming from a ticket that he bought at a gasoline station in his home town of Lethbridge. To give an idea of the odds he faced, he had a 1 in about 33.3m chance of winning the first of those jackpots, the WCLC’s bulletin said.
The media outlet NOW Toronto added that Serkin had won another $250,000 lottery jackpot more than a decade before his newer streak of good fortune.
At least part of his lottery success seems to involve consistently playing the odds. He told officials he has been playing the lottery since 1982 – but he maintained that is because he simply enjoys the ritual of buying his tickets and then checking them.
“You check your ticket and if you win – you’re happy,” Serkin said. “If you don’t, you can always try again.
“I’m a cancer survivor and I’m retired, so I am just grateful for all of it.”
Serkin said he bought his latest triumphant ticket on a whim while buying gasoline, figuring, “What do I have to lose?”
He said his friends’ reacted by saying “not again?!” when he took them out for coffee and informed them he had hit the jackpot once more.
As Serkin put it, his wife was equally incredulous – and, if history was any indication, a memorable vacation was in store for her.
“I took my wife to Hawaii with the last win, and we had a great time,” Serkin said to officials. “Now, we’re going to Newfoundland.”
https://www.theguardian.com/world/2025/ ... r-jackpots
Cancer survivor David Serkin won draws in August, November and May, and another more than a decade ago
Ramon Antonio Vargas
Wed 11 Jun 2025 10.00 BST
Share
How do you say “lottery winner” in western Canada? The answer is: David Serkin, the name of the cancer survivor from Alberta who won three separate lottery jackpots between August and May to accumulate about $2.5m in prize money.
According to officials, those lucky tickets marked the second, third and fourth times Serkin had won a lottery in his life, a feat that he had vanishingly small chances of pulling off and gained notice on corners of the internet dedicated to charming news stories.
“I know the odds are astronomical, [and] I don’t think it’ll happen again,” Serkin said in a press bulletin issued recently by the Western Canada Lottery Corporation (WCLC). “But I still like buying tickets.”
Serkin won draws of $500,000 on 20 August, $1m on 16 November and $1m on 3 May, the last of those coming from a ticket that he bought at a gasoline station in his home town of Lethbridge. To give an idea of the odds he faced, he had a 1 in about 33.3m chance of winning the first of those jackpots, the WCLC’s bulletin said.
The media outlet NOW Toronto added that Serkin had won another $250,000 lottery jackpot more than a decade before his newer streak of good fortune.
At least part of his lottery success seems to involve consistently playing the odds. He told officials he has been playing the lottery since 1982 – but he maintained that is because he simply enjoys the ritual of buying his tickets and then checking them.
“You check your ticket and if you win – you’re happy,” Serkin said. “If you don’t, you can always try again.
“I’m a cancer survivor and I’m retired, so I am just grateful for all of it.”
Serkin said he bought his latest triumphant ticket on a whim while buying gasoline, figuring, “What do I have to lose?”
He said his friends’ reacted by saying “not again?!” when he took them out for coffee and informed them he had hit the jackpot once more.
As Serkin put it, his wife was equally incredulous – and, if history was any indication, a memorable vacation was in store for her.
“I took my wife to Hawaii with the last win, and we had a great time,” Serkin said to officials. “Now, we’re going to Newfoundland.”
https://www.theguardian.com/world/2025/ ... r-jackpots