On Christmas Day 2002 a West Virginia man won $315 million. A few years later he said he wished he had torn up the ticket. He was 55, a contractor who had built his own company and was already worth more than $17 million. On Christmas Eve 2002 he stopped at a store in Hurricane, West Virginia, and bought a Powerball ticket. The next night it hit. $314.9 million, at the time the biggest jackpot ever won on a single ticket in America. He took the cash. About $113 million after taxes. At first he did what a good man would do. He pledged 10% to churches. He put $14 million into a foundation. He bought the deli manager who sold him the ticket a house, a Jeep and a check for $44,000. Then the money started pulling in the wrong people. In 2003 thieves took $545,000 in cash from his car outside a strip club. Asked why he carried that much, he said: “Because I can.” His granddaughter Brandi was the light of his life. He gave her about $2,000 a week. At 17 she had four cars. New friends came. Then drugs. Her boyfriend was found dead of an overdose in one of her grandfather’s houses. A few months later Brandi disappeared. On December 20, 2004, she was found dead, wrapped in a plastic sheet behind a junked van. “My granddaughter’s dead probably because of the money,” he said. His wife said she wished she had torn up the ticket. He said he wished the same. His daughter died in 2009. His house burned down in 2016. He died in 2020. “I don’t like what I’ve become,” he said. His name was Jack Whittaker. Would you still take the $315 million? Yes or no.

She won $1 million in the Michigan Lottery and kept using food stamps. When a reporter asked why, she said: “I have bills to pay.” She was 24, a young mother from the Detroit suburbs. In 2011 she won $1 million on a Michigan Lottery TV game show. She took the lump sum. After taxes, a little over half was left. She paid cash for a house. She bought a new car. And every month she kept using her state food card: $200 in groceries, paid for by taxpayers. A local TV station got a tip and found her unloading groceries from her car. The reporter asked if she thought it was right. “I thought that they would cut me off, but since they didn’t, I thought maybe it was okay because I’m not working.” Do you think you have a right to that money? “I kind of do. I have no income and I have bills to pay.” She owned two houses at the time. “I’m struggling,” she said. The clip went national. Lawmakers rushed out bills to cross-check lottery winners against welfare rolls. She was charged with fraud, pleaded no contest, paid back about $5,500 and got probation. A friend said people kept showing up to take advantage of her. “What’s the point of having money if you’re not going to have happiness?” In September 2012, a few months after her sentence, she was found dead of an apparent drug overdose. She was 25. Her name was Amanda Clayton. Was she a cheat, or a kid who never should have been handed a million dollars?

At 15 he dropped out of school and moved into the YMCA. At 60 he was crowned king of his high school prom. He was born in 1932 to parents who were not married. A couple adopted him at six weeks old. When he was five, his adoptive mother died. His father remarried again and again and moved them from town to town. They ate most of their meals in cheap diners. The boy loved those diners. They felt like the family he did not have. At 12 he lied about his age to get a job at a restaurant, working the night shift. He had already been fired twice that year. His father told him he would never be able to hold a job. He decided to prove him wrong. At 15 he quit high school, moved into the YMCA and became a busboy. He washed dishes, cooked, and learned every job in the kitchen. In his twenties he met an old man in a white suit who was selling a chicken recipe, Colonel Sanders. He helped turn around four failing chicken restaurants and sold his share back. He was a millionaire at 35. In 1969 he opened his own hamburger place in Columbus, Ohio, and named it after his eight-year-old daughter. Decades later, while he was giving a speech about the value of education, a high school student challenged him to practice what he preached. So at 60 he hired a tutor, studied and passed his GED. His graduating class voted him “most likely to succeed.” He and his wife were crowned king and queen of the prom. His name was Dave Thomas. His daughter’s nickname was Wendy. What was your first job, and how old were you?

Pete Rose got more hits than anyone in baseball history. Then he lied about one thing for 14 years. In the video below, he finally answers the question he dodged for 14 years. His 4,256 hits are still the all-time record. He played like every inning was the World Series. America called him Charlie Hustle. But in 1989 an investigator hired by baseball found evidence that Rose, then managing the Cincinnati Reds, had been betting on baseball, including on his own team. Betting slips. Phone records. An investigator says that most nights at 7:15 he called his bookie from the clubhouse. Rose denied it. Under oath. In public. “I never bet on baseball,” he said, for years. On August 24, 1989, he accepted a lifetime ban without admitting anything. Then in 2004, at 62, he admitted it. Yes, he bet on baseball. Yes, on his own team. But never against it, he said: “I believed in my team.” “I was wrong. Just stupid. Worst thing I ever did in my life.” He was never reinstated while he was alive. He died in 2024, at 83. Months later, baseball removed him from the banned list, which means a committee can now vote him into the Hall of Fame. Does Pete Rose belong in the Hall of Fame, or did he lose that right the day he bet on his own team?

Anna Nicole Smith was 26 when she married an 89-year-old oil billionaire. He died 14 months later, and his will did not leave her a cent. In the video below, she answers the word everyone used for her, and his son’s lawyer answers back. She was a small-town Texas girl who became a Playboy Playmate and the face of Guess jeans. He was J. Howard Marshall II, one of the richest men in Texas, with an estate later valued at up to $1.6 billion. They married in 1994. He spent millions on her, by some estimates close to $12 million. “Forget about the damn age,” she said. “He saved my life and I saved his life.” She said she was not a gold digger. Fourteen months after the wedding, he died. His will left almost everything to his son, Pierce. Anna said her husband had always promised her half. Pierce’s lawyer said the old man had given her enough while he was alive: “Most of us can get along on $12 million.” A Texas jury gave her nothing. A California court awarded her about $474 million. The fight went to the U.S. Supreme Court twice. Pierce died in 2006. Anna died in 2007. In 2011 the Supreme Court’s final ruling meant her side would get nothing. She never collected a cent. Did Anna Nicole Smith deserve half his fortune, or was $12 million already more than enough?

Larry King was married to Shawn for 22 years. Two months after filing for divorce, he wrote a will by hand, and her name was not in it. In the video below, you see the will itself, and Shawn explains why she never thought it would come to this. Larry King interviewed about 50,000 people in a career that lasted more than six decades. He married eight times, to seven women. His marriage to Shawn, a singer and actress, lasted 22 years, the longest of all. They had two sons. In August 2019, at 85, he filed for divorce. It was never finalized. “In my heart I didn’t think it was really going to happen,” Shawn said. Some reports say they still spoke every day. Two months after filing, he wrote a new will by hand. “This is my last will and testament. It should replace all previous writings.” He wanted 100% of his money split equally among his five children. You can see where he crossed out “20%” and wrote “100%.” Shawn’s name was not in it. In 2020 two of those children died, weeks apart. Larry died in January 2021, at 87. Shawn went to court. She said they had a “watertight” family estate plan from 2015, and that someone must have influenced him. His oldest son, Larry Jr., fought her. Reports put his fortune at around $50 million, much of it held in trusts. Was it Larry’s right to cut her out, or should 22 years of marriage count for something?

In 2012 a Chicago man won $1 million on a scratch-off ticket. The day after the state issued his check, he was dead. Doctors said natural causes. He was 46, an immigrant from India who had built up a few dry-cleaning shops in Chicago. He scratched the ticket at his local 7-Eleven and shouted, “I hit a million!” The Illinois Lottery took his photo holding the ticket, smiling. He chose the lump sum. After taxes, about $425,000. He planned to pay off mortgages, grow his business and give some to charity. On July 19 the state issued his check. That night, after a family dinner at home, he reportedly began screaming in pain. Before dawn on July 20 he was dead. There was no sign of trauma. The medical examiner ruled it natural causes, hardening of the arteries. No autopsy. He was buried. On August 15 the check was cashed. But a relative called the medical examiner’s office. It didn’t seem natural, the family said. Take a closer look. They reran the blood tests with a wider screen. Months later the result came back: a lethal dose of cyanide. Routine tests had never looked for it. His death was ruled a homicide. His body was exhumed, but there was nothing more to find. He had died without a will, and his widow and his siblings went to court over the money. No one has ever been charged. His name was Urooj Khan. Should lottery winners be allowed to stay anonymous? Yes or no.

In 2001 a broke man in Kentucky borrowed money to get his water turned back on and spent $7 on Powerball tickets. He won $27 million. Twelve years later he died with nothing. He was 46, out of work, an ex-con who had done time for robbing a gas station. He bought the tickets in August 2001 at a gas station in Ashland, Kentucky. He was one of four winners of a $280 million jackpot. He took the lump sum: $27 million after taxes. He told reporters he wanted to accept it with humility. He wanted the money to last for his daughter and for generations. Then he showed a TV crew his new life. “I never have to worry about a hotel room, what I pay, worry about a menu.” He bought a Bentley. His fiancée got her Ferrari. Then a Lamborghini, mansions in Palm Beach and Palm Springs, a Learjet, racehorses, a $178,000 diamond ring and a $78,000 watch. He spent about $12 million in the first year. Then came the drugs. Police found cocaine and needles in the mansion. The homes, the cars and the jet went to foreclosure. By 2007 the couple was living in a warehouse where they had stored their collectibles, until they were evicted from that too. He went home to Ashland broke and sick. In 2013 he died in a hospice at 58. Alone, the papers said, and penniless. His name was David Lee Edwards. If you won $27 million tomorrow, would you trust yourself with it? Yes or no.

In 1967 a young man stopped for a hurt old man lying by a Nevada highway. Nine years later he was named in a will worth $156 million. He was 23, driving alone at night on a desert highway north of Las Vegas. He saw an old man lying in the dirt by the road. The man was thin, dirty and hurt. The young man took him for a drifter or an old prospector. He offered to take him to a hospital. The old man refused. He just wanted a ride to Las Vegas. So he drove him there and dropped him off behind the Sands Hotel. Along the way the old man told him who he was. The young man did not believe him. In April 1976 the old man died. He was one of the richest men in America, and nobody could find his will. People punched holes in walls looking for it. Three weeks later an envelope turned up at church headquarters in Salt Lake City. Inside was a handwritten will. One line left a sixteenth of the estate, about $156 million, to a name nobody recognized. The young man from the desert. By then he ran a small gas station in Utah. At first he said he knew nothing about it. Then his fingerprint was found on the envelope. He admitted he had delivered it and said a stranger had left it at his gas station. In 1978 a jury decided the will was a forgery. He never got a penny. He never changed his story. Decades later a retired FBI agent said a pilot claimed he had flown the old man to a brothel near that same highway that very night. Others call it nonsense. Hollywood made a movie about him that won two Oscars. His name was Melvin Dummar. He died in 2018. The old man in the desert, he always said, was Howard Hughes. Was he a liar, or the unluckiest man in America?

In 1980 Americans lined up to sell their grandmother’s silver forks. Two brothers in Texas were the reason. Their father was a Texas oil billionaire. In the 1970s the sons feared inflation and did not trust paper money. So they started buying silver. Not paper contracts. Real bars. They chartered planes to fly them to vaults in Switzerland. By the end of 1979 they and their partners controlled about 195 million ounces. Some estimates put it at a third to half of the world’s deliverable supply. Then the price went crazy. Under $10 an ounce in the summer of 1979. Nearly $50 in January 1980. Every $1 jump made them about $100 million on paper. Across America people lined up to sell their silver bowls, candlesticks, knives and forks to be melted down. Tiffany ran an ad in the New York Times calling it “unconscionable.” But much of it was bought with borrowed money. The exchanges changed the rules, limiting new buying. The price started to fall, and the brokers wanted more cash. On March 27, 1980, they did not come up with it. Silver crashed to $10.80. It became known as Silver Thursday. A group of banks put together a $1.1 billion loan to keep the family afloat. Asked about the losses, the older brother said: “A billion dollars isn’t what it used to be.” Six months later the younger brother told a TV reporter he was as bullish on silver as the day he started. In 1988 a jury found they had conspired to corner the market. They filed for bankruptcy. They were Nelson Bunker Hunt and Herbert Hunt, sons of H.L. Hunt. Bunker was once called one of the richest men in the world. Geniuses beaten by a rule change, or did they get what they deserved?

On a snowy day in 1963, a company older than the Civil War told its workers it was leaving town. It started as a blacksmith shop in 1852. Its wagons rolled west with the pioneers and carried supplies for the Union Army. Later it built cars, and at one point it employed about 24,000 people in one Indiana city. For generations it was the job in town. Fathers, sons, uncles and grandfathers on the same line. On December 9, 1963, the company announced it was closing the plant. Less than three weeks before Christmas. More than 6,000 people out of work at once. Eleven days later the last car came off the line. Then came the second blow. The pension fund did not have enough money to pay what it had promised. Workers 60 and older got their full pension. About 3,600 people. Workers between 40 and 59 with at least 10 years got about 15 cents for every dollar they had been promised. About 4,000 people. Everyone else got nothing. About 2,900 workers. Men in their fifties who had given the company their whole working lives walked out with a small check and no retirement. Their story reached Washington. It took more than ten years. On Labor Day 1974, President Gerald Ford signed a law that set rules for workplace pensions and created a federal insurance fund that pays workers when a pension plan fails. The company was Studebaker, in South Bend. The law is ERISA. If you have a workplace pension or a 401(k) today, you are covered by the law those workers made necessary. Should a company ever be allowed to walk away from a pension promise? Yes or no.

He owned 10% of a company for 12 days. Then he sold it for $800. In 1976 he was 41, an engineer at a video game company in California. A young coworker and his friend kept fighting over their little business idea. He sat them down in his apartment and settled it in under an hour. The young coworker said, right there, “We are going to form a company.” The friends would get 45% each. He would get 10% and break the ties. He typed up the partnership contract himself. He drew the first company logo by hand. Then he started to worry. Years earlier his own slot machine business had failed, and it took him a year to pay off the debts. In a partnership, every partner is personally on the hook. The two young men had almost nothing. He had a house, a bank account and a car. If it all went wrong, the creditors would come for him. So 12 days later he went to the county office and had his name taken off the contract. He got $800 for his 10%. Months later came a $1,500 check to sign away any future claim. He signed. Years later he found his copy of the founding contract in a filing cabinet and sold it to a dealer for $500. In 2011 it sold at auction for more than $1.3 million. He says that is his one regret. The young coworker was Steve Jobs. His friend was Steve Wozniak. The company was Apple. His name is Ronald Wayne. In 2010 he was living on Social Security in the Nevada desert. He says if he had stayed, he would probably have ended up “the richest man in the cemetery.” “I’ve never been rich,” he says. “But I’ve never been hungry either.” Did he make the worst mistake in business history, or the right call?