In 2011, Charlie Sheen was earning $1.8 million per episode of Two and a Half Men. Four days after Warner Bros. fired him, he sued the studio and creator Chuck Lorre for $100 million. In the video below, Lorre explains how he handled the early warning signs: "I was determined to stay in denial. I just didn’t want to know." Sheen’s lawsuit claimed the studio stopped production to punish him after he publicly attacked Lorre. He insisted he was "ready, willing and able to work" and demanded compensation for the eight episodes canceled that season. Warner Bros. saw it differently. The studio cited Sheen’s conduct as “dangerously self-destructive” and said his behavior had undermined production. The dispute went beyond a lost job. Sheen was one of television’s highest-paid actors, but his public war with his bosses had put a hit show and its remaining season at the center of a $100 million legal battle. After Ashton Kutcher replaced him, the show returned without Sheen. Warner announced a settlement soon afterward, but the terms were confidential. Reports put the figure anywhere from $25 million to about $100 million. Years later, Sheen and Lorre reconciled. In 2023, Lorre cast Sheen in Bookie, bringing the two back together professionally. Was Warner Bros. right to fire a star whose behavior threatened the show, or did Sheen have a case for the money he believed he was owed?

Dwyane Wade earned $196 million in the NBA. He says he was sure he was going to lose everything. His first marriage alone ended with $5 million, a mansion and four cars. In the video below, Wade admits that getting married without a prenup was one of his biggest financial mistakes and explains why he would do things differently today. Wade made his first million at 21. “Within four years of me getting money, I’m in the court for lawsuits,” he said. He trusted no one for six or seven years. The divorce was filed in 2007. In 2010, a judge ordered his then-wife into custody after she missed a hearing. Wade testified for about six hours: “I had no knowledge where my kids were and I got very afraid.” He won sole custody in 2011. In July 2013, his ex-wife sat down on a busy Chicago street and said Wade had left her homeless. His lawyer disputed that account, saying Wade had been paying her $25,000 a month, plus her mortgage and the fees of 16 lawyers. Three days later, a judge approved the settlement: $5 million, the family mansion and four cars. His lawyer called it “very generous.” Today, Wade chairs JPMorgan’s new Athlete Council, which teaches athletes how to handle their first big contracts. Looking back, he says he’d tell his 21-year-old self to “slow down.” Was it a “very generous” deal, or the price of one costly mistake?

In 2011, Arnold Schwarzenegger admitted he had fathered a child with Mildred Baena, the family’s housekeeper, while married to Maria Shriver. Their son, Joseph, was born in 1997. In the video below, Schwarzenegger speaks to Piers Morgan about the scandal. The headline says it all: “My children were disappointed.” For years, Schwarzenegger had been one of Hollywood’s biggest stars. He had built a political career, becoming governor of California in 2003, with Maria and their four children beside him. But the affair had happened years earlier, while Baena was working in their household. Joseph grew up without the public knowing the full story. Schwarzenegger’s wife and children eventually learned what had happened, and the revelation became a worldwide scandal. In 2011, Schwarzenegger publicly acknowledged Joseph as his son. He later described the moment as one of his biggest personal failures. Maria separated from him that year. After 25 years of marriage, their family life had changed forever. In his interview with Morgan, Schwarzenegger admitted that his children were disappointed in him. He had spent years building a public image as a successful actor, politician and family man. Then the people closest to him learned about the secret he had kept. Can a father earn back his children’s trust after something like this?

In 2011, Gina Rinehart’s children went to court over a family trust worth more than $4 billion. They were supposed to gain control when the youngest turned 25. Instead, the date was pushed to 2068. In the video below, Gina’s son John talks about the dispute with his mother. The trust had been created by their grandfather, mining magnate Lang Hancock. Gina was the trustee, while her four children were the beneficiaries. When the youngest approached 25, Gina changed the date. She argued that her children were not ready to manage billions of dollars and could face major tax liabilities. Her children challenged the decision in court. The dispute lasted until 2015, when a judge removed Gina as trustee and appointed her daughter Bianca instead. By then, the trust was worth more than $4 billion. The money had been set aside for the children. The fight was over who had the right to control it. Was Gina protecting her children from a fortune they weren't ready to manage, or did she simply refuse to give up control?

In 2011, Arnold Schwarzenegger’s wife discovered he had fathered a child with their housekeeper. The couple had been married for 25 years. In the video report below, the story behind the breakup unfolds. Schwarzenegger later called the affair “the stupidest thing” he had done in the relationship. The boy was born in 1997. Schwarzenegger kept the truth hidden while building a Hollywood career and serving as governor of California. When Maria Shriver learned the truth, she moved out. Their separation became public, ending one of Hollywood’s most prominent marriages. During a 2012 interview with 60 Minutes, Schwarzenegger was asked whether he had lied to his wife. "You can say that," he replied. He later described the affair as "the stupidest thing I’ve done in the whole relationship." A secret he had kept for years ended a marriage that had lasted a quarter of a century. Can a marriage survive a secret like that, even after 25 years together?

In 2026, 95-year-old Warren Buffett revealed that Steve Jobs once called him for advice on whether Apple should buy back its own stock. Through the second quarter of 2026, Apple has spent more than $880 billion on repurchases. Jobs already believed Apple’s shares were selling for less than they were worth, but he wanted to hear Buffett’s view before deciding. Buffett told him only two questions mattered. First: did Apple have all the money it needed to build the business Jobs had in his head for the next five or ten years? Jobs said yes, they had plenty. Second: was Apple’s stock selling for less than it was worth? Jobs said it was selling for a lot less. Buffett’s answer was immediate: “Well, you’ve answered your own question.” Jobs still didn’t buy back the shares. Buffett later said he believed Jobs was hoping to hear a different answer, because keeping the cash gave Apple more flexibility for the opportunities Jobs believed were still ahead. Apple began its large-scale repurchase program in late 2012, about a year after Jobs died, and kept it going. Neither question depends on a market forecast or on where the stock trades next year. Buffett has used essentially the same logic at Berkshire for decades, while Apple became one of the largest share repurchasers in corporate history. What would you have told Steve Jobs?

Brooke Astor died at 105 with a fortune of about $180 million. Two years later, a jury convicted her son of looting it. In October 2009 a jury found him guilty on 14 counts, including fraud, conspiracy and grand larceny. Jurors found he took money from his mother and changed her will while she was incompetent and had Alzheimer’s. Her estate lawyer, Francis Morrissey, was found guilty on all six counts he faced. Marshall’s lawyers argued he had the legal power to make gifts to himself and that his mother was lucid when she changed her will. It started in 2006, when her grandson, Philip Marshall, filed for guardianship of her and accused his father of neglect. Anthony Marshall settled the elder abuse allegations that October. He returned some money, jewelry and artwork, and gave up control of her finances. Marshall was 85 at sentencing. The judge gave him 1 to 3 years, the minimum allowed. Prosecutors had asked for 4½ years. Appeals kept him out of prison for more than 3½ years. In March 2013 an appeals court upheld the conviction, though it threw out one grand larceny count. He entered prison that June and was granted medical parole about two months later. He died in 2014, at 90. She had given about $200 million to New York, including the Metropolitan Museum of Art and the New York Public Library, and spent decades deciding where the rest would go. At the end, a jury found, her son changed her will. Was Anthony Marshall a son who looked after his mother, or a man who looked after her money?

A 31-year-old heir to the Ray-Ban fortune says his billionaire father gave the family everything except love. Now, a €40 billion family empire is caught in a succession battle. In an interview on Pulp Podcast, Leonardo Maria Del Vecchio was asked about the inheritance dispute involving his seven siblings. His father, Leonardo Del Vecchio, founded Luxottica, the eyewear giant behind Ray-Ban. When he died in 2022, he left behind a business empire worth tens of billions of euros. But the heirs still haven't settled the succession. At the center of the dispute are €300 million in bequests to Francesco Milleri, the longtime executive who now leads EssilorLuxottica. “It's not the inheritance that's blocked. They're fighting over €300 million,” Leonardo said. He insists the money was left according to his father's wishes and says he will continue to defend them, regardless of his personal relationship with Milleri. Eight heirs, a €40 billion holding company, and a family still fighting over their father's final wishes. How does a fortune this big fail to bring a family together?

In 2017, Warren Buffett was asked what quality matters most in a partner for a lasting marriage. His answer wasn’t intelligence, beauty, or a sense of humor. In the video below, Buffett explains why he would choose someone with "few expectations." He could have named loyalty, patience, or shared values. Instead, he went with a quality that sounds funny until you think about it. A partner with fewer expectations may be less focused on what you should earn, buy, or achieve. That leaves more room for appreciating who you already are. Buffett has spent decades observing people, money, and relationships. His answer suggests that happiness depends partly on how much we expect from others. The joke works because everyone knows how quickly expectations can turn into disappointment. Even a successful relationship can feel like a failure when one person is constantly measuring the other against an ideal. Money can buy comfort, gifts, and opportunities. It cannot guarantee that two people will be satisfied with each other. Buffett’s advice is funny, but it also raises an uncomfortable question. Are lasting relationships built on finding the perfect partner, or on expecting less perfection from the person you choose? Sometimes the secret to a happy marriage isn’t finding someone who has everything. It’s finding someone who doesn’t expect you to be everything.

In 2008, Irish businessman Seán Quinn had a fortune estimated at billions of dollars. Then one enormous bet on Anglo Irish Bank helped destroy the business empire he had spent decades building. In the video below, Quinn discusses how his investment turned into one of Ireland’s most notorious financial collapses. Quinn built his fortune from a small family quarry. Over the years, he expanded into manufacturing, insurance, property, and other businesses. Then he began betting heavily on Anglo Irish Bank shares. He used financial contracts that gave him massive exposure to the bank’s stock price without having to buy all the shares outright. At one point, his position represented roughly 25% of the bank. His fortune was now heavily tied to the fate of a single financial institution. When the financial crisis hit in 2008, Anglo Irish Bank’s shares collapsed. Quinn faced mounting losses and demands for more money to cover his positions. The bank’s situation continued to deteriorate until the Irish government nationalized it in 2009. Quinn’s investment had turned into a financial disaster. He lost control of his business empire and was declared bankrupt in 2011. The man once described as Ireland’s richest person had seen his fortune unravel. Quinn later acknowledged that his decision to keep betting on the bank was a catastrophic mistake. Decades of business success could not protect him from a position that had grown too large. He spent decades building an empire, only to watch it collapse because of one enormous bet. How much of your fortune would you risk on a single investment?

In 2019, a 54-year-old unemployed man in New Jersey almost lost a $273 million lottery jackpot because he was distracted by his phone. Mike Weirsky had been out of work for 15 years. He bought two Mega Millions tickets for $2 each, put them on the counter, checked his phone, and walked out without them. The next day, he returned to the store. Someone had found the tickets and turned them in instead of keeping them. The store held them for him, and Weirsky proved they were his. He didn't check the numbers until Sunday. When he finally scanned one ticket, it showed he had won $273 million. He sat down and told his mother. She asked him what that meant. The person who returned the tickets could have claimed the jackpot by signing them, lottery officials said. Weirsky later said he wanted to find that person and give them something, because without their honesty, he would have had nothing. He chose a lump-sum payment of $162.5 million before taxes. His first planned purchase was a Ford Raptor pickup, followed by a new car for his mother and repairs to her house. A man who had spent 15 years without a job suddenly had more money than he could ever have expected. But the strangest part of the story is that the jackpot almost belonged to someone else. Would you have returned the tickets, knowing they could be worth $273 million?

In 1977, Warren Buffett's wife left him at 44. She moved to San Francisco to pursue a singing career, but she never divorced him. Susan Buffett had married Warren in 1952, when she was just 19. Years later, she told him she wanted to sing, and after moving away, she introduced him to another woman, Astrid Menks, asking her to look after him. The three remained close for decades. They even signed Christmas cards together, and Susan and Astrid stayed part of Warren's life until Susan's death. In 2004, Susan died from a cerebral hemorrhage in a hotel room in Cody, Wyoming. Warren later described her as "the sun and I was the moon reflecting her light." He also said she taught him something he hadn't understood when they first met: "She taught me love before I knew what it was." Her Berkshire Hathaway stake was worth roughly $3 billion, and she left it to the foundation that now carries her name. Two years later, Warren pledged more than 99% of his remaining fortune to philanthropy. The woman who left Omaha to sing never stopped shaping his life, and eventually her name became attached to the work he decided to leave behind. Do you think Warren's relationship with Susan changed the way he viewed money and wealth?

In 2015, 19-year-old Olivia Mead went to court over a $1.2 billion family fortune. Her father left her $3 million. Her two older half-sisters received roughly $400 million each. In the video below, Olivia talks about the inheritance fight with her billionaire father. Her father, mining magnate Michael Wright, died in 2012. Olivia had grown up largely apart from him. "For a long time I thought that maybe he didn't love me," she later said. When Wright died, Olivia's $3 million was placed in a trust that she could not fully access until she was 30. She took the estate to court. A judge awarded her $25 million. The family appealed. In 2017, the appeals court cut the amount to about $6.1 million. Olivia had gone to court over $3 million. She left with $6.1 million. Her two older sisters had received roughly $400 million each. Was Olivia asking for too much, or was $3 million too little for the daughter of a billionaire?

In 2011, Gina Rinehart’s children went to court over a family trust worth more than $4 billion. They were supposed to gain control when the youngest turned 25. Instead, the date was pushed to 2068. In the video below, Gina’s son John talks about the dispute with his mother. The trust had been created by their grandfather, mining magnate Lang Hancock. Gina was the trustee, while her four children were the beneficiaries. When the youngest approached 25, Gina changed the date. She argued that her children were not ready to manage billions of dollars and could face major tax liabilities. Her children challenged the decision in court. The dispute lasted until 2015, when a judge removed Gina as trustee and appointed her daughter Bianca instead. By then, the trust was worth more than $4 billion. The money had been set aside for the children. The fight was over who had the right to control it. Was Gina protecting her children from a fortune they weren't ready to manage, or did she simply refuse to give up control?

"My business model is The Beatles." In 2003, Steve Jobs explained why the greatest businesses aren't built by one brilliant person. He wasn't talking about music. Jobs believed The Beatles were successful because the four members balanced each other. Each person had strengths the others didn't, and together they were far more effective than they could have been alone. "Great things in business are never done by one person. They're done by a team of people." Jobs saw the same principle at Apple. The goal wasn't to surround himself with people who agreed with him. It was to bring together talented people who could challenge each other, cover each other's weaknesses, and build something none of them could create alone. He also understood the danger that comes with success. "All of us need to be on guard against arrogance, which knocks at the door whenever you're successful." For Jobs, building a great company wasn't about becoming the smartest person in the room. It was about building a room full of people who were exceptionally good at what they did.