Soloway

Macaulay Culkin had a fortune reportedly worth $15–20 million. His family was facing eviction. The money existed. Getting access to it meant removing his own parents from control. The boy from Home Alone had become one of the world’s most recognizable children. Behind the scenes, his parents were fighting over custody of him and his siblings. In a 2004 interview with Larry King, Culkin said legal bills had consumed his parents’ money. His mother could no longer afford the rent. He did not even know how much he had in the bank. “I didn't have a bed. I didn't even have a room.” He said he and his brother had been sleeping on a couch despite the money he was earning. Culkin explained that roughly 80% of his money was locked in a trust until he turned 18. His parents had legal guardianship over the remaining portion. As a teenager, he removed both their names and put an accountant he trusted in charge. The story became a Hollywood legend about a child who “divorced” his parents after they stole his fortune. Culkin rejected that version. His parents had not stolen all his money. He had changed who controlled it. That distinction matters. You can be wealthy on paper and still depend on someone else’s permission to use what you earned. If a child earns enough to support the entire family, should the parents still control the money?

Frank Rosenthal ran four Las Vegas casinos linked to the mob. On October 4, 1982, someone planted a bomb beneath his Cadillac. He survived, but could never identify who had wanted him dead. Rosenthal had just left Tony Roma’s restaurant when the explosion tore through his car. In this interview, he says he never heard the initial blast. He remembers fire shooting up from the floor toward the windshield. He reached for the door with his left hand. The heat forced him to pull it back. Then he reached across with his right arm, pushed his shoulder against the door and tumbled outside. Investigators believed a steel plate beneath the driver’s seat helped deflect the explosion. It was part of the Cadillac’s design, not armor Rosenthal had installed. The man trusted to run a casino empire had survived because of something he had not planned. Years later, an interviewer asked whether he had considered revenge. “First of all, revenge on who?” Rosenthal said identifying whoever planted or ordered the bomb would be speculation. The case remained unsolved. Robert De Niro would portray a character based on him in Casino. But the real story lacked the certainty a film can give its audience: Rosenthal escaped the burning car without learning who had put him inside it. Running the business did not mean knowing who could decide your future. Would you walk away from that empire, or keep working when you could not tell which relationship had become a threat?

Patrizia Reggiani arranged the murder of her ex-husband, Maurizio Gucci. Years later, an Italian court ruled that his heirs still owed her the annual payment he had promised before she had him killed. On March 27, 1995, a gunman shot Gucci outside his Milan office. The heir to one of the world’s most recognizable fortunes was 46. His marriage had ended, and he had a new partner. His former wife had not moved on. In 1998, Reggiani was convicted of organizing the murder and sentenced to 29 years in prison, later reduced to 26 on appeal. The plot involved her psychic adviser, a hotel doorman, a gunman and a getaway driver. Then came the financial twist. Before his death, Gucci had signed an agreement promising her an annual payment of 1.1 million Swiss francs. Years after her conviction, a Milan appeals court ruled that the agreement remained enforceable. The heirs were their two daughters. Their mother had arranged their father’s murder. Now she was pursuing payments from the fortune they inherited from him. This was not a court declaring her innocent or rewarding the killing. It was a ruling that her conviction did not extinguish that separate contractual obligation. The criminal case sent her to prison. The civil agreement still entitled her to money. Should arranging someone’s murder automatically cancel every financial promise they ever made to you?

Dan Bilzerian says he won roughly $70 million playing poker against just three wealthy men. But another number complicates his story: a family trust he says once stood at $96 million. The man famous for displaying his fortune has spent years defending where it came from. In this 2021 interview with Graham Bensinger, Bilzerian describes watching that trust shrink to roughly $1.5 million. He also discusses signing away a third of his interest to help free his father. His explanation for the lifestyle everyone recognizes is different: enormous winnings in private poker games. Those winnings are his claims, not an independently verified record. But look at what he is claiming. Not that he defeated thousands of professionals. That he won around $70 million from three wealthy opponents. If his account is accurate, the opportunity depended on more than understanding cards. He needed access to people who could afford to lose extraordinary amounts, and a reason for them to keep playing. That is the uncomfortable distinction between being good at a game and finding a profitable one. The toughest opponent can give you prestige. The wealthiest opponent can give you a fortune. If you could win millions from someone who kept losing, would you stop inviting them? Follow for more stories where money makes the answer uncomfortable.

On November 20, 1974, British MP John Stonehouse left his clothes on a Miami beach and disappeared. His wife believed he had drowned. A month later, police found him alive in Australia, using a dead man’s identity. His businesses were collapsing. Stonehouse had obtained false identities and moved money overseas, preparing a new life away from his creditors, constituents and family. But moving the money created a trail. Bank accounts under different names attracted suspicion. On Christmas Eve, his disappearance stopped being a mystery and became a criminal investigation. Then came the television interview. Stonehouse was still an MP. Asked about continuing to receive his parliamentary salary while thousands of miles from his constituency, he described his escape as a “fact-finding tour.” Not just geographically, he explained, but into his own personality. The man who had staged his death was now explaining why taxpayers should keep paying him. In 1976, he was sentenced to seven years for offences including fraud and theft. A new identity could hide his name. It could not erase the transactions. Money leaves a second biography of your life. Unlike the story you tell people, you do not get to rewrite every copy. Would you trust someone more after an honest confession, or less after hearing how convincingly they explain the deception?

In August 1991, Warren Buffett’s $700 million investment became a rescue mission. A trader had broken the rules. His bosses had found out. The government was only learning about it months later. Salomon Brothers had submitted unauthorized bids using customers’ names to buy more U.S. government debt than the rules allowed. Senior executives knew about misconduct but failed to report it promptly. When the scandal became public, the firm faced losing access to Treasury auctions. Buffett became interim chairman on August 18. That same day, the Treasury announced restrictions that threatened the company’s survival. He personally appealed to Treasury Secretary Nicholas Brady. The government partially relaxed the ban, giving Salomon room to keep operating. Then Buffett appeared before Congress and delivered a warning to his employees: “Lose a shred of reputation for the firm, and I will be ruthless.” The uncomfortable detail was not just that a trader had cheated. It was that people above him had known and allowed the problem to remain hidden. A trading loss damages your balance sheet. Concealing it makes people question every number on it. What destroys a financial institution faster: the original misconduct, or discovering that management knew?

Patty Hearst’s family spent $2 million trying to get her back from kidnappers. On April 15, 1974, a bank camera captured the missing heiress carrying a rifle alongside them. Two months earlier, armed radicals had abducted the 19-year-old granddaughter of newspaper magnate William Randolph Hearst. Their demand was unusual: distribute food to the poor. Her family funded a $2 million program. The food went out. Patty did not come home. Instead, recordings arrived in which she denounced her family and announced allegiance to the group that had kidnapped her. Then came the bank robbery. The woman America had been searching for was now someone the FBI wanted to arrest. Hearst later said she had been confined, threatened and sexually assaulted. Prosecutors argued she had become a willing participant. In 1976, a jury convicted her of bank robbery. President Carter later commuted her sentence; President Clinton pardoned her in 2001. Her family could afford the kidnappers’ demands. What they could not buy was a guarantee that paying would end the nightmare. That is the danger of a ransom: the person taking your money still controls whether the deal is honored. When a kidnapped person commits a crime under threat, where does survival end and responsibility begin?

Katrina Bookman’s slot machine displayed nearly $43 million. The casino offered her a steak dinner instead. In August 2016, she took a selfie beside the screen at Resorts World Casino in New York. For a moment, a mother of four believed her family’s future had changed. Then she was told to come back the next day. The casino said the machine had malfunctioned. Her actual payout was $2.25. But there was another number that made the dispute stranger: the machine’s maximum jackpot was only $6,500. The screen had displayed a fortune the game was never designed to pay. New York’s gaming regulator confirmed the malfunction. The machine carried a disclaimer: “Malfunctions void all pays and plays.” Bookman’s lawyer argued that she should at least receive the $6,500 maximum. The regulator said even that payout was not permitted. The casino had a technical explanation. Bookman had a photograph of its machine telling her something entirely different. That is the uncomfortable distinction: a number on a screen is not necessarily money you are entitled to collect. Should the casino owe her anything beyond $2.25, or does a malfunction disclaimer settle it?

El Chapo admitted that drugs destroy lives. Then, in a secret interview recorded while he was a fugitive in 2015, he explained why he believed none of it was his fault. Four years later, a U.S. court ordered him to forfeit $12.6 billion. In the video, Guzmán sits calmly as an interviewer asks whether he is responsible for drug addiction around the world. His answer, translated into English: “No, that is false, because the day I don’t exist, it’s not going to decrease in any way at all.” That was his defense. Someone else would sell the drugs. Customers would keep buying. Removing him would not remove the market. But his organization did far more than meet demand. Evidence at his trial described billions in laundered proceeds, officials paid to protect the business, and rivals kidnapped, tortured and killed to maintain control. He wanted credit for building the empire while treating its consequences as something that would have happened anyway. On July 17, 2019, he received life in prison plus 30 years. The $12.6 billion forfeiture order was not a verified balance in his bank account. It was a judgment against the proceeds of his crimes. His argument exposes a convenient escape from responsibility: if someone else would do it, your own decision supposedly stops mattering. Does an inevitable market make its suppliers less responsible, or is “someone else would do it” simply the most profitable excuse in the world?

Jimmy Hoffa helped finance mob-linked Las Vegas casinos with money truck drivers were saving for retirement. By 1963, the pension fund held $213 million. The casinos needed money. The workers needed a secure future. Hoffa helped connect the two. Loans from the Teamsters’ Central States Pension Fund helped finance properties including the Stardust, Fremont and Desert Inn. Workers who might never enter those casinos were helping fund the businesses behind them. The uncomfortable part: a casino could repay its loan while the mob skimmed money from its profits. According to FBI evidence, approximately $100,000 a month was being skimmed from those three casinos in the early 1960s. A profitable investment could still strengthen organized crime. When Hoffa went to prison in 1967, the casino financing continued. Under his successor, the loans grew larger. After his release, Hoffa fought to regain control of the union. On July 30, 1975, he went to a meeting with two reputed mob figures and disappeared. His body was never found. Nobody has been directly charged with his disappearance. This 1964 interview shows him before prison, before the comeback, before the disappearance. The workers owned the savings. Other people decided what those savings would build. If a casino repaid the loan with interest, would you accept your retirement money financing it even knowing who else profited?

The U.S. put a $1 million price on Manuel Noriega’s arrest. Just months earlier, he had been Panama’s most powerful man and, according to U.S. officials, a multimillionaire with alleged ties to drug trafficking. Noriega had once worked with American intelligence. Now Washington wanted him captured. Officials estimated his fortune at $200–$300 million and moved to freeze assets they believed he had sent abroad. When U.S. forces invaded Panama in December 1989, Noriega disappeared into the Vatican Embassy. Outside, American troops kept up the pressure. Inside, the man who had ruled Panama was running out of options. On January 3, 1990, he surrendered. The military ruler was flown to the United States to face drug-trafficking charges. The money mattered. But it could not buy him a way out once his political protection collapsed. Noriega’s story is a brutal lesson in the difference between wealth and power: if your fortune depends on who obeys you, it can vanish the moment they stop.

Volkswagen sold roughly 11 million diesel cars with software that could recognize an emissions test. In the U.S., some emitted up to 40 times the legal limit once they were back on the road. In the video below, Volkswagen’s U.S. boss admits the company lied. What he doesn’t explain on that stage is how long it kept going after the numbers stopped adding up. Researchers found the gap between lab results and real driving in 2014. Volkswagen spent the next 18 months offering regulators other explanations while hiding the software. Its engineers had even added steering-wheel angle detection to help the cars recognize when they were on a test rig. Then the company’s U.S. boss walked onstage to launch a new car. “Our company was dishonest with the EPA… We have totally screwed up.” Volkswagen later agreed to pay $4.3 billion in U.S. criminal and civil penalties. The detail I can’t get past is the steering wheel: the car wasn’t just built to pass the test. It was built to know when the test had begun.

On April 10, 1962, John F. Kennedy thought he had prevented a price increase that could reach almost every American household. Hours later, the head of U.S. Steel walked into the White House and told him the price was going up anyway. The increase was just $6 per ton. That was the trap: steel went into cars, appliances and homes. A small number at the factory could become a higher bill for millions of people. Kennedy’s administration had helped secure a restrained deal with steelworkers to keep prices stable. Now U.S. Steel had announced an increase, and other producers were following it. The next day, Kennedy went on television. He called the companies’ actions “wholly unjustifiable and irresponsible.” Then he said something colder: “In the last 24 hours we had their answer.” But the ending was not a new law forcing prices down. Some steelmakers refused to follow the increase. The others faced a choice: keep the extra $6, or risk losing buyers to competitors. They backed down. Kennedy confronted the executives. Competition made the reversal possible. Watch his face in the footage. He knew the fight was never only about $6.

In 1935, Adolf Hitler stood inside the Krupp factory and asked its workers to repay him with their votes. “If YES, then stand up for me, just as I stood up for you.” To the workers, this was a speech about jobs and loyalty. What they could not see was how those jobs were being financed. Krupp had helped establish Mefo, a front company used to conceal the debt funding Germany’s rearmament. The factory behind Hitler was part of a war machine being built before the war began. By 1939, each expansion he had made without a major war had strengthened his belief that Britain and France would back down again. He invaded Poland expecting that pattern to hold. This time, they declared war. The chilling part of the footage is how confidently he asks people to trust him. He had turned borrowed money into weapons and previous concessions into certainty. Then he bet a country on the assumption that nobody would stop him.

In 1973, kidnappers demanded $17 million from the richest man in the world for the return of his 16 y.o. grandson. J. Paul Getty refused to pay until they mailed the boy’s severed ear to a newspaper. Getty controlled an oil fortune worth more than $1 billion. The ransom would not have threatened his wealth, but he believed paying it would turn every member of his family into a target. “If I pay one penny now, I’ll have 14 kidnapped grandchildren.” For five months, John Paul Getty III was held captive in the mountains of southern Italy. When the family still refused to pay, his kidnappers cut off his right ear and sent it with a warning that more pieces would follow. The original demand was eventually negotiated down from $17 million to approximately $3 million. Getty agreed to provide $2.2 million, reportedly the maximum amount his advisers said could qualify for a tax deduction. He did not simply cover the remaining $800,000. He loaned it to his own son at 4% interest. The ransom was paid, and the teenager was discovered alive beside an Italian highway. When he later called his grandfather to thank him, Getty reportedly refused to come to the phone. Getty had spent a lifetime treating every dollar as capital. That discipline helped make him one of the richest men alive, but it also reached a point where even his grandson’s survival became a negotiation. The lesson is not that every expense should be avoided. It is that the rules used to build a fortune can become dangerous when you forget what the fortune was supposed to protect.

On February 19, 1986, Barry Seal drove his white Cadillac into the same parking space the government required him to use every evening. He had reportedly earned up to $50 million flying cocaine for the Medellín Cartel. But after federal charges threatened to bury him, one of the cartel’s trusted pilots became a DEA informant. Seal returned undercover with hidden cameras inside his aircraft. He filmed cartel members loading hundreds of kilograms of cocaine and captured rare evidence connecting Pablo Escobar directly to an international shipment. Then details of the operation reached the press. Seal’s identity was exposed, yet a judge still ordered him to spend every night at a Salvation Army halfway house in Baton Rouge. His location and arrival time were predictable. Protection was offered, but he refused it. “I’m not worried about the contract.” At approximately 6 p.m., assassins were waiting beside his parking space. They opened fire before Seal could leave his Cadillac. Three men were later convicted, and prosecutors said the cartel had paid for the killing. Seal knew how to hide an aircraft carrying cocaine from radar. What killed him was making his own routine impossible to hide. Sometimes the most valuable information is simply knowing where someone will be tomorrow.

Alexandre Cazes built a $1 billion darknet empire before turning 26. The FBI caught him using a fake car accident and one mistake he had forgotten for years. “See if you can spot the moment when he realizes he’s about to be arrested.” In 2014, Cazes launched AlphaBay from his laptop. More than 200,000 users and 40,000 vendors used it to trade drugs, stolen identities, malware and weapons. Cazes collected a commission from every transaction and estimated his personal fortune at $23 million. Tor concealed his location. Encryption protected his data. Cryptocurrency moved the money. But AlphaBay’s earliest welcome emails contained Cazes’ personal Hotmail address. Investigators connected it to his real identity and followed the money to Thailand. On July 5, 2017, undercover agents crashed a car into the gate of his Bangkok mansion. Cazes walked outside to investigate, leaving his laptop open, unencrypted and logged into AlphaBay’s administrator account. Police arrested him before he could lock it. Seven days later, he was found dead in a Thai jail cell. The footage below captures the trap. The FBI showed the original recording once at a cybersecurity conference, then refused to release it publicly. A journalist secretly recorded these few seconds from the screen. AlphaBay survived every sophisticated investigation until one forgotten email connected the entire empire to its creator. The greatest weakness in an anonymous system is rarely the technology. It is the person who starts believing the technology made him invisible.

In 1933, Aristotle Onassis bought six ships worth roughly $12 million for just $120,000. The world thought shipping was finished. He saw the largest forced sale of his lifetime. The Great Depression had crushed global trade. Ships were sitting idle, freight rates had collapsed, and established owners were desperate to escape the industry. Onassis borrowed the money and paid approximately $20,000 for each vessel, close to their scrap value. Then he waited. He kept the ships inactive until demand began returning, put them back to work, and used the cash flow to expand into oil tankers. By 1945, he controlled six ships. Ten years later, his fleet had grown to 77. The assets had not suddenly become better. The world around them had changed. Onassis made his fortune because he bought productive machinery from owners who could no longer afford to wait. Most people study what an asset is worth today. The wealthy study what the current owner may be forced to accept. A crisis does not destroy value equally. It transfers valuable assets from people who need cash now to people who can survive until later.

John Paulson made approximately $4 billion in one year by betting against an investment almost every major institution considered safe. In 2005, American house prices were still rising. Banks were issuing mortgages to borrowers who could barely afford them, packaging those loans into securities, and selling them with high credit ratings. Paulson noticed something the market was ignoring: the weakest mortgages did not need to collapse immediately. Defaults only had to rise enough for the securities built on top of them to break. His fund bought credit default swaps, effectively insurance against those mortgage bonds. For months, the trade lost money while housing continued climbing. Investors questioned him. Banks dismissed him. The cost of waiting kept increasing. Then the defaults arrived. In 2007, Paulson’s firm reportedly made about $15 billion. Paulson personally earned nearly $4 billion while many of the institutions on the opposite side were approaching collapse. The obvious lesson is that he predicted the housing crash. The useful lesson is that he designed the trade so being early was expensive, but being right was transformational. Most people search for predictions. Great investors search for asymmetry. A strong thesis is not enough. The real advantage is finding a structure where the potential loss is defined and the potential reward is disproportionately large. Reply “EDGE” and I’ll send you the framework I use to identify asymmetric opportunities.