The money stories behind famous people. Big bets, costly mistakes, unexpected comebacks

Joined December 2022
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Manchester United lost roughly $128 million in a year and still paid shareholders about $37 million. After a 4–0 defeat to Brentford, Gary Neville went after the owners on live TV. August 13, 2022. United had conceded four goals in 35 minutes. Jamie Redknapp argued that the expensive players on the pitch had to take responsibility. Neville wanted the conversation to go higher. It got personal: “Look at me when I’m talking to you,” Redknapp demanded. Neville wasn’t backing down. He pointed to money leaving the club while Old Trafford deteriorated. The Glazers, he argued, were letting their employees take the criticism while they stayed in America. Then he challenged the defence everyone kept making: the owners had spent money on players. Whose money? Neville’s point was that United funded those transfers through its own revenue and borrowing. Spending the club’s money wasn’t the same as putting your own money into it. The accounts published the following month added another uncomfortable detail. For the financial year ending June 2022, United had paid about $37 million in dividends to shareholders, including the Glazers, despite a roughly $128 million loss. United had finished sixth. That hadn’t stopped shareholders getting paid.
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Manchester United lost roughly $128 million in a year and still paid shareholders about $37 million. After a 4–0 defeat to Brentford, Gary Neville went after the owners on live TV. August 13, 2022. United had conceded four goals in 35 minutes. Jamie Redknapp argued that the expensive players on the pitch had to take responsibility. Neville wanted the conversation to go higher. It got personal: “Look at me when I’m talking to you,” Redknapp demanded. Neville wasn’t backing down. He pointed to money leaving the club while Old Trafford deteriorated. The Glazers, he argued, were letting their employees take the criticism while they stayed in America. Then he challenged the defence everyone kept making: the owners had spent money on players. Whose money? Neville’s point was that United funded those transfers through its own revenue and borrowing. Spending the club’s money wasn’t the same as putting your own money into it. The accounts published the following month added another uncomfortable detail. For the financial year ending June 2022, United had paid about $37 million in dividends to shareholders, including the Glazers, despite a roughly $128 million loss. United had finished sixth. That hadn’t stopped shareholders getting paid.
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Ryan Reynolds and Rob McElhenney bought Wrexham for about $2.5 million. Their club later received roughly $24 million in taxpayer-funded grants. Then reporters started asking for the paperwork. The money was intended to help upgrade the stadium for international events. Officials said the improvements would bring visitors, jobs and investment to the area. But in April 2026, a Guardian investigation raised questions about the first grant, worth approximately $5 million. According to the report, the council awarded it before completing its final subsidy assessment or signing a funding agreement. The agreement wasn’t completed until September 2025. The council defended its process, saying due diligence had been carried out before any money was transferred. Meanwhile, Wrexham was attracting private investors too. In December 2025, Apollo Sports Capital announced a minority investment. Reynolds and McElhenney remained majority owners. In the video below, McElhenney remembers people laughing when they first mentioned reaching the Premier League. Three promotions later, that ambition looked much closer. The financial debate had changed too: how much public money should help fund a club that wealthy private investors already wanted to own?
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Ryan Reynolds and Rob McElhenney bought Wrexham for about $2.5 million. Their club later received roughly $24 million in taxpayer-funded grants. Then reporters started asking for the paperwork. The money was intended to help upgrade the stadium for international events. Officials said the improvements would bring visitors, jobs and investment to the area. But in April 2026, a Guardian investigation raised questions about the first grant, worth approximately $5 million. According to the report, the council awarded it before completing its final subsidy assessment or signing a funding agreement. The agreement wasn’t completed until September 2025. The council defended its process, saying due diligence had been carried out before any money was transferred. Meanwhile, Wrexham was attracting private investors too. In December 2025, Apollo Sports Capital announced a minority investment. Reynolds and McElhenney remained majority owners. In the video below, McElhenney remembers people laughing when they first mentioned reaching the Premier League. Three promotions later, that ambition looked much closer. The financial debate had changed too: how much public money should help fund a club that wealthy private investors already wanted to own?
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In 2011, Wrexham had 24 hours to find £100,000 or face being kicked out of its league. A 10-year-old boy showed up with his £35 savings. The club needed a £250,000 financial guarantee to be allowed to start the season. Its co-owner had put up £150,000. The deadline passed with the rest still missing, and the league granted one extra day. Then the supporters started turning up. A fan in Canada sent £10,000. Two men offered the deeds to their homes as collateral. Others offered their life savings. The boy brought £35. At the ground, people handed over cash in envelopes and checks. An ITV reporter covering the appeal remembered a grown man approaching him with tears in his eyes. “I wish I could have given more.” By the end of the day, supporters had raised £127,000. Wrexham received confirmation that it could compete, with the opening game just four days away. Later that year, the Wrexham Supporters’ Trust took control of the club. Years before the worldwide audience and the promotion celebrations, these were the people keeping Wrexham alive. They were paying for the chance to come back on Saturday. That boy’s £35 became part of the money that made it possible.
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In 2011, Wrexham had 24 hours to find £100,000 or face being kicked out of its league. A 10-year-old boy showed up with his £35 savings. The club needed a £250,000 financial guarantee to be allowed to start the season. Its co-owner had put up £150,000. The deadline passed with the rest still missing, and the league granted one extra day. Then the supporters started turning up. A fan in Canada sent £10,000. Two men offered the deeds to their homes as collateral. Others offered their life savings. The boy brought £35. At the ground, people handed over cash in envelopes and checks. An ITV reporter covering the appeal remembered a grown man approaching him with tears in his eyes. “I wish I could have given more.” By the end of the day, supporters had raised £127,000. Wrexham received confirmation that it could compete, with the opening game just four days away. Later that year, the Wrexham Supporters’ Trust took control of the club. Years before the worldwide audience and the promotion celebrations, these were the people keeping Wrexham alive. They were paying for the chance to come back on Saturday. That boy’s £35 became part of the money that made it possible.
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Ryan Reynolds and Rob McElhenney were counting on a $25 million grant to help rebuild Wrexham’s stadium. The government said no. “I don’t have £20 million lying around,” McElhenney admitted. In 2023, Wrexham missed out on £20 million from the UK government’s Levelling Up Fund — roughly $25 million at the time. The money was meant to help redevelop the Kop, the stand behind one of the goals. The cameras on Welcome to Wrexham caught their reaction. Reynolds called it a huge problem. Their adviser said they would have to find another way. Ryan broke the tension with a joke: “I’ll sell one of my children.” Later that year, with the permanent redevelopment still unresolved, the club announced a temporary stand with 2,289 seats. But there was a detail in the announcement that stood out: building it would cost more than the club expected to recover through ticket sales. They approved it anyway. Demand had grown, and supporters were struggling to get tickets. The board decided that getting more fans inside the ground was worth the expense. The temporary stand opened in December 2023, as Wrexham beat Newport County 2–0. They couldn’t deliver the permanent stand yet. They could give more fans somewhere to watch.
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Ryan Reynolds and Rob McElhenney were counting on a $25 million grant to help rebuild Wrexham’s stadium. The government said no. “I don’t have £20 million lying around,” McElhenney admitted. In 2023, Wrexham missed out on £20 million from the UK government’s Levelling Up Fund — roughly $25 million at the time. The money was meant to help redevelop the Kop, the stand behind one of the goals. The cameras on Welcome to Wrexham caught their reaction. Reynolds called it a huge problem. Their adviser said they would have to find another way. Ryan broke the tension with a joke: “I’ll sell one of my children.” Later that year, with the permanent redevelopment still unresolved, the club announced a temporary stand with 2,289 seats. But there was a detail in the announcement that stood out: building it would cost more than the club expected to recover through ticket sales. They approved it anyway. Demand had grown, and supporters were struggling to get tickets. The board decided that getting more fans inside the ground was worth the expense. The temporary stand opened in December 2023, as Wrexham beat Newport County 2–0. They couldn’t deliver the permanent stand yet. They could give more fans somewhere to watch.
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Ryan Reynolds wanted to throw up when he heard Wrexham had lost over $12 million. By March 2025, the club had repaid roughly $19 million in loans and interest to his and Rob McElhenney’s company. And they still owned a stake in it. When they took over in 2021, Wrexham was a Welsh soccer club stuck in the fifth tier of English football. In a meeting shown on Welcome to Wrexham, they asked how much money they were losing. “Loads,” came the answer. The club’s adviser put the estimate above £10 million — more than $12 million at the time. Reynolds felt sick. McElhenney wanted to know when they would get paid if they kept the club. In April 2023, Wrexham finally won promotion back to the Football League after 15 years away. That’s the moment in the video below. Reynolds is struggling to process it. People had kept asking why they bought Wrexham. With the stadium celebrating around him, he had his answer: “This is exactly why Wrexham.” McElhenney talks about the town, the supporters, and what it means to have been welcomed into their community. The money started coming back, too. By March 2025, the club had repaid about £15 million in shareholder loans and interest. That was repayment of money lent to the club, not £15 million in profit. A month later, Wrexham secured its third consecutive promotion. A team they had bought in the fifth tier was now one division below the Premier League. They had recovered their shareholder loans while keeping a stake in what Wrexham could become.
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They bought the club. The stress came at no extra charge.
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Veltrix retweeted
Ryan Reynolds wanted to throw up when he heard Wrexham had lost over $12 million. By March 2025, the club had repaid roughly $19 million in loans and interest to his and Rob McElhenney’s company. And they still owned a stake in it. When they took over in 2021, Wrexham was a Welsh soccer club stuck in the fifth tier of English football. In a meeting shown on Welcome to Wrexham, they asked how much money they were losing. “Loads,” came the answer. The club’s adviser put the estimate above £10 million — more than $12 million at the time. Reynolds felt sick. McElhenney wanted to know when they would get paid if they kept the club. In April 2023, Wrexham finally won promotion back to the Football League after 15 years away. That’s the moment in the video below. Reynolds is struggling to process it. People had kept asking why they bought Wrexham. With the stadium celebrating around him, he had his answer: “This is exactly why Wrexham.” McElhenney talks about the town, the supporters, and what it means to have been welcomed into their community. The money started coming back, too. By March 2025, the club had repaid about £15 million in shareholder loans and interest. That was repayment of money lent to the club, not £15 million in profit. A month later, Wrexham secured its third consecutive promotion. A team they had bought in the fifth tier was now one division below the Premier League. They had recovered their shareholder loans while keeping a stake in what Wrexham could become.
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Shaquille O’Neal says he walked away from a $40 million Reebok deal after a woman slapped $2,000 out of his hand. She was angry about how much his sneakers cost. He was leaving an arena when she confronted him. Kids wanted his shoes. Parents had to find the money. Shaq says he had about $2,000 in his pocket. He offered it to her, explaining that he didn’t set the prices. She knocked it away and told him to make shoes families could actually afford. In the video below, he explains what happened next. He told Reebok to keep the money. He would keep wearing their shoes for the season, but he wanted to build his own brand. Then he made a deal with Walmart. His shoes would sell for $19 to $29. But lowering the price was only part of it. “It’s not that kids don’t want to wear $20 shoes. They don’t want to wear shoes that look like they cost $20.” He brought in designers who had worked at Reebok. By 2021, he said they had sold more than 400 million pairs. He offered one woman $2,000. She wanted him to fix the price for everyone else.
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RYAN REYNOLDS. A $27 BOTTLE OF GIN. A DEAL WORTH UP TO $610 MILLION. In 2018, Reynolds bought a stake in Aviation Gin, a brand from Portland, Oregon, and took charge of its creative direction. One of his early ads was an interview with his fictional twin, Gordon. Reynolds played both parts. Gordon asks whether he invented gin. Then questions why a Canadian who can’t fly a plane is selling Aviation American Gin. Ryan eventually walks out of his own interview. The bottle stays in the shot. Behind the jokes, the business was growing. In 2019, Aviation’s sales volume more than doubled. According to Diageo, it accounted for 40% of the growth in the US super-premium gin segment that year. In August 2020, Diageo announced an agreement to acquire Aviation and Davos Brands, including three other spirits brands, for up to $610 million. The announced terms were $335 million upfront, with up to $275 million more tied to Aviation’s performance over ten years. Reynolds’ exact stake wasn’t disclosed. He retained an ownership interest and remained involved in marketing. That’s what makes the clip more interesting than a celebrity commercial. Every joke was promoting a business he partly owned. The gin already existed. He gave people another reason to remember its name.
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RYAN REYNOLDS. A $27 BOTTLE OF GIN. A DEAL WORTH UP TO $610 MILLION. In 2018, Reynolds bought a stake in Aviation Gin, a brand from Portland, Oregon, and took charge of its creative direction. One of his early ads was an interview with his fictional twin, Gordon. Reynolds played both parts. Gordon asks whether he invented gin. Then questions why a Canadian who can’t fly a plane is selling Aviation American Gin. Ryan eventually walks out of his own interview. The bottle stays in the shot. Behind the jokes, the business was growing. In 2019, Aviation’s sales volume more than doubled. According to Diageo, it accounted for 40% of the growth in the US super-premium gin segment that year. In August 2020, Diageo announced an agreement to acquire Aviation and Davos Brands, including three other spirits brands, for up to $610 million. The announced terms were $335 million upfront, with up to $275 million more tied to Aviation’s performance over ten years. Reynolds’ exact stake wasn’t disclosed. He retained an ownership interest and remained involved in marketing. That’s what makes the clip more interesting than a celebrity commercial. Every joke was promoting a business he partly owned. The gin already existed. He gave people another reason to remember its name.
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BY 2013, BRYAN CRANSTON WAS REPORTEDLY MAKING $225,000 PER EPISODE OF BREAKING BAD. AS A KID, HE WATCHED HIS FAMILY LOSE THEIR HOME. His father was an actor, too. Work came and went, and the family’s lifestyle moved with it. One year, they had a newer car. The next, they traded down to an old one. They put in a swimming pool. Later, his mother said they couldn’t afford the chemicals to maintain it. Then his father left. The house went into foreclosure, and Bryan and his brother went to live with their grandparents. Years later, when Malcolm in the Middle gave Cranston a steady television paycheck, he remembered how quickly things could fall apart. He told ROUTE magazine that he and his wife saved the money and funded a college savings plan for their daughter. “We didn’t go out and buy anything.” He connected those decisions directly to what had happened to his family. He wanted to save, stay involved as a father, and keep his ego from making the decisions. Breaking Bad brought a much bigger level of fame. By its final season, TV Guide was reporting his salary at $225,000 an episode. But the habit of putting money away was already there. The detail that stays with me is that swimming pool. His family could afford to build it in a good year, then couldn’t afford to maintain it in a bad one. That’s an expensive way for a child to learn the difference between having money and being able to count on it.
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BY 2013, BRYAN CRANSTON WAS REPORTEDLY MAKING $225,000 PER EPISODE OF BREAKING BAD. AS A KID, HE WATCHED HIS FAMILY LOSE THEIR HOME. His father was an actor, too. Work came and went, and the family’s lifestyle moved with it. One year, they had a newer car. The next, they traded down to an old one. They put in a swimming pool. Later, his mother said they couldn’t afford the chemicals to maintain it. Then his father left. The house went into foreclosure, and Bryan and his brother went to live with their grandparents. Years later, when Malcolm in the Middle gave Cranston a steady television paycheck, he remembered how quickly things could fall apart. He told ROUTE magazine that he and his wife saved the money and funded a college savings plan for their daughter. “We didn’t go out and buy anything.” He connected those decisions directly to what had happened to his family. He wanted to save, stay involved as a father, and keep his ego from making the decisions. Breaking Bad brought a much bigger level of fame. By its final season, TV Guide was reporting his salary at $225,000 an episode. But the habit of putting money away was already there. The detail that stays with me is that swimming pool. His family could afford to build it in a good year, then couldn’t afford to maintain it in a bad one. That’s an expensive way for a child to learn the difference between having money and being able to count on it.
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$35 MILLION FOR ONE DAY OF WORK. GEORGE CLOONEY DISCUSSED IT WITH HIS WIFE AND SAID NO. The offer was for an airline commercial. A single day of filming would have earned him more than many leading actors get for an entire movie. But the airline was associated with a country he had concerns about. Before accepting, he talked it through with his wife, Amal, a human rights lawyer. They decided to pass. Clooney told the story in a 2021 interview after being asked whether he ever felt he had enough money. He didn’t name the airline or the country. He just explained what made the offer unacceptable to him: “If it takes a minute’s sleep away from me, it’s not worth it.” Of course, he was already wealthy. Walking away wouldn’t put his home or his family’s future at risk. Still, $35 million is a lot of money to leave on the table, even when you don’t need it. He had reached a point where another paycheck wasn’t enough reason to say yes.
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$35 MILLION FOR ONE DAY OF WORK. GEORGE CLOONEY DISCUSSED IT WITH HIS WIFE AND SAID NO. The offer was for an airline commercial. A single day of filming would have earned him more than many leading actors get for an entire movie. But the airline was associated with a country he had concerns about. Before accepting, he talked it through with his wife, Amal, a human rights lawyer. They decided to pass. Clooney told the story in a 2021 interview after being asked whether he ever felt he had enough money. He didn’t name the airline or the country. He just explained what made the offer unacceptable to him: “If it takes a minute’s sleep away from me, it’s not worth it.” Of course, he was already wealthy. Walking away wouldn’t put his home or his family’s future at risk. Still, $35 million is a lot of money to leave on the table, even when you don’t need it. He had reached a point where another paycheck wasn’t enough reason to say yes.
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MILA KUNIS LOOKED AT TIFFANY’S PRICES AND BOUGHT A $90 WEDDING RING ON ETSY. ASHTON KUTCHER’S COST $100. In 2016, Conan noticed the thin band on her finger. Nothing flashy. So she told him where it came from. She’d wanted a simple wedding band. Then she checked the prices at Tiffany’s and couldn’t justify what she was seeing. She opened Etsy, found one for $90, and bought it. Two Hollywood stars. Two wedding bands. $190 total. Conan praised her for being frugal. “That’s a nice way of saying ‘cheap,’ but yes.” There’s a detail that makes this story better: Ashton had already given her a beautiful engagement ring. She told Conan she hardly ever wore it. The $90 band was the one she was happy wearing around. And according to Mila, the Etsy seller had no idea whose ring they were making. Imagine fulfilling an ordinary order, then finding out your customer is showing it off on national television. What I like here is that she knew exactly what she wanted before she saw the price. Being able to afford more didn’t change the brief.
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MILA KUNIS LOOKED AT TIFFANY’S PRICES AND BOUGHT A $90 WEDDING RING ON ETSY. ASHTON KUTCHER’S COST $100. In 2016, Conan noticed the thin band on her finger. Nothing flashy. So she told him where it came from. She’d wanted a simple wedding band. Then she checked the prices at Tiffany’s and couldn’t justify what she was seeing. She opened Etsy, found one for $90, and bought it. Two Hollywood stars. Two wedding bands. $190 total. Conan praised her for being frugal. “That’s a nice way of saying ‘cheap,’ but yes.” There’s a detail that makes this story better: Ashton had already given her a beautiful engagement ring. She told Conan she hardly ever wore it. The $90 band was the one she was happy wearing around. And according to Mila, the Etsy seller had no idea whose ring they were making. Imagine fulfilling an ordinary order, then finding out your customer is showing it off on national television. What I like here is that she knew exactly what she wanted before she saw the price. Being able to afford more didn’t change the brief.
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