Question of the Day - 23 December 2025

Yesterday, we examined the details of forming lottery and Megabucks pools and how the money and tax liabilities are distributed in the case of hitting the jackpot. Today, we describe some of the most interesting real-world coworker lottery pool cases that both went smoothly and blew up into major legal battles.

We'll start with the success stories. 

In 2011, a big workplace pool at Kaiser Permanente in California won a Mega Millions jackpot for $315 million. There were seven winners, six lab technicians and one receptionist. Each reportedly received roughly $21 million before federal taxes (California doesn't collect state taxes on lottery jackpots) and other withholdings. They had email records documenting who paid in and every participant’s payment was logged and Lotto officials issued individual checks to each member of the pool.

In 2012, the “Three Amigos” school workers were three public school employees in Maryland who won what was then the largest jackpot in U.S. history – a $656 million Mega Millions payout. The three had a longstanding pool with clear contributions, they formed a trust to claim the prize anonymously, and each got an equal share with no disputes. They did everything right: had rules, kept records, and moved quickly to structure the claim legally. 

Then there was the Michigan "Breakfast Club" that won an $842.4 million Powerball jackpot in June 2024. The group consisted of three people, a married couple and -- dig this -- their attorney. They had an agreement that they'd split any winnings three ways. They opted for the lump-sum payment, netting about $305 million after taxes. The lawyer collected the jackpot and they never saw even a hint of disagreement or conflict over the split. 

Then there are the disaster stories. 

In 2005, 12 workers at a restaurant in Oregon had a long-running pool. The manager allegedly took the winning ticket for herself, then quit her job and tried to claim the jackpot. The group sued. The Oregon Lottery froze the payout and a judge forced the manager to share the jackpot with the group.

In 2009, a group of New Jersey construction workers won a $38.5 million jackpot. A supervisor who didn’t contribute that week claimed he should still get a share, because he was “always” in the pool. A lawsuit ensued, a long court battle raged, and the ruling was that only people who paid that week were entitled to a share. Missing even one week can cost you millions.

In 2013, an Indiana hairdresser in a pool with seven of her co-workers hit a state jackpot for $9.5 million. The hairdresser who bought the winning ticket claimed it was a personal purchase, separate from the tickets she bought with pooled money. The co-workers claimed the winning ticket was part of a group lottery pool and that there was an "unwritten rule" that the person buying the group's tickets couldn't buy personal tickets at the same time or location. The hairdresser claimed the numbers on the winning ticket were "personal." She also contended she was never informed of any such unwritten rule against doing so. But her case fell apart when the numbers on the winning ticket turned out to be a quick pick. A judge blocked the lottery from paying the jackpot to the hairdresser, ruling the co-workers had a reasonable likelihood of success in a lawsuit. Before the case went to trial, the parties reached a confidential settlement through negotiations, allowing the money to be paid out. 

Also in 2013, a hotel housekeeper in Florida found a discarded lottery ticket and gave it to her boss, thinking it was trash. The ticket turned out to be a winner. The boss tried to claim the jackpot as her own. The housekeeper sued. The court ruled that the maid had no legal claim, since she didn’t buy the ticket for a pool. However, the boss had committed fraud in filing documents. The whole thing was settled confidentially, believed to be split, with some held in trust. 

None of these cases are as horrendous as one from 1999, in which an Alabama Waffle House waitress won a $10 million jackpot from a ticket given her as a tip by a regular customer. Her Waffle House coworkers sued her, claiming an oral agreement to split any winnings from tipped lottery tickets. A lower court initially sided with the coworkers, but the Alabama Supreme Court eventually ruled in the winner's favor, stating the agreement was an unenforceable gambling contract under state law. The customer who gave her the ticket also sued, alleging she'd promised to buy him a new pickup truck if she won. This case was also dismissed due to lack of an enforceable contract. The waitress placed her winnings into a corporation to manage the funds, distributing shares to her family. The IRS demanded she pay gift taxes. A U.S. Tax Court eventually ruled that the value of the "gifts" was lower than the IRS claimed, due to all the ongoing legal expenses, which reducing her tax liability. Finally, a few years after winning the jackpot, the waitress' ex-husband kidnapped her at gunpoint, demanding money from the winnings. She managed to wrestle the gun away and shot him in the chest in self-defense. She wasn't charged, but the ex-husband, who survived the gunshot, was.