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$464 MILLION IN CASH, EARNING UNDER 0.1%. Paris Jackson says that is where her father’s estate sits. Michael Jackson died in 2009 with more than $500 million in debt. His will put the estate in a trust. 40% for his mother, 40% for his three children, 20% for charity. It named two executors, John Branca and John McClain. As of June 2024 the estate was valued at over $2 billion. In November 2025 his daughter Paris challenged the 2021 accounting in court. She alleges the executors were paid $148 million through 2021 and that $464 million sits in cash earning under 0.1%. In 2026 a court referee ruled that $625,000 in 2018 bonuses to three law firms must go back to the estate. He also acknowledged the executors’ exceptional services. The executors say Paris has received about $65 million from the estate, and that they turned the debt into one of the biggest businesses in music. The court has not ruled on the $148 million or the $464 million. Both are her claims. Who should have the final say on what the people running an estate are paid?

Jessica Alba and Cash Warren split everything they built from 2008 to 2024, down to the art on the walls. JESSICA ALBA MUST PAY HER EX $5 MILLION. IT COMES FROM ONE HOUSE. Jessica Alba and Cash Warren married on May 19, 2008. They separated on December 27, 2024. In March, a judge signed off on the divorce, and a March 16 filing obtained by E! News shows how the money is split. Everything built during the marriage is community property and is divided equally. That includes investments in WeWork and Culver Studios, stocks, and even the furniture and art from their former home. On top of that, Alba must pay Warren $5 million from the sale of one of their jointly owned homes, and set aside $500,000 for the children's expenses. Then come the terms that matter most for her career. Warren also receives 50% of her acting royalties and residuals from roles during the marriage, plus 50% of her restricted shares in The Honest Company. In return, she receives half of his profits from producing projects in the same period. Money from projects made before the marriage, and after the separation, stays individual property. Neither pays child support to the other for now, and both waived any future spousal support. The most expensive line is not the $5 million. It is the calendar. December 27, 2024 is the date her career stopped being shared. Watch the video below for the details. Should royalties from the marriage years be split 50/50?

Juventus paid a reported €100 million for Cristiano Ronaldo. Years later, he had to take them to court for about €19.5 million in wages. CRISTIANO RONALDO HAD TO SUE JUVENTUS FOR €19.5 MILLION HE SAYS HE EARNED. In 2018 Juventus paid Real Madrid a reported €100 million for him. It was one of the biggest transfers in football history. Then 2020 hit. During the pandemic the club asked its players to take pay cuts. Ronaldo's side says part of his wages was deferred, not cancelled: about €19.5 million in total. Juventus says there was no official deferral agreement. He left for Manchester United in 2021. The money never came. So he went to arbitration. In April 2024 the panel ordered Juventus to pay about half, around €9.75 million, plus interest and about €80,000 in legal costs. The other half was not awarded. Juventus appealed. A Turin court dismissed the appeal. The club says that ruling only looked at procedural points, not the merits. It did not stop there. Juventus took the case to Italy's Court of Cassation. As of mid October there is no hearing date. Ronaldo has already received the €9.75 million, and Juventus says the cost has been in its accounts since the 2023-24 season. So the club paid €100 million to get him, and is still in court over the wages. Watch the video below for the details. Who is right here: the player who says the money was deferred, or the club that says nothing was signed?

The Notorious B.I.G. died in 1997. In 2026, his estate company owes $12.5 million to his mother's trust. BIGGIE'S ESTATE ORDERED TO PAY $12.5 MILLION TO HIS LATE MOTHER'S TRUST. On October 27, a Delaware judge ruled that $12,518,336 in distributions from Notorious B.I.G., LLC is owed to the trust of Voletta Wallace, Biggie's mother. The company manages his name and music. Faith Evans is its sole manager. Her side had asked the court to limit the payout to $48,612. The judge rejected that. Here is how it got here. In 2007, Evans and Voletta Wallace formed the company to manage Biggie's intellectual property. When Voletta died in February 2025, her stake went into a trust. Weeks before her death she named producer and former manager Wayne Barrow as sole trustee. In 2025, Barrow sued, saying Evans kept the trust from receiving its share. In August 2026 the court sided with him and dismissed her counterclaim. The October ruling put the number on it: money the company distributed, plus interest. Barrow's lawyer says it could approach $14 million. The backdrop is a catalog deal. In 2025, Primary Wave bought a 50% stake in Biggie's catalog and likeness, reported at the time at around $100 million. Other reports put the valuation near $200 million. This is not a personal fine for Evans. It is money the trust says the company owed it. Evans' lawyer declined to comment. No appeal has been reported. It is also not the end of the story. Biggie's son C.J. Wallace has filed a separate case in Pennsylvania, challenging the change that made Barrow trustee. He says it was signed 15 days before Voletta died. Barrow denies improper influence. The Delaware ruling does not decide that fight. Watch the video below for a breakdown. Who should control a legend's music 29 years later: his widow, his family, or an outside trustee?

$64 MILLION FOR HER SHARE OF A WINERY. Angelina Jolie sold it in 2021. Brad Pitt has been in court over it ever since. Brad Pitt and Angelina Jolie bought Château Miraval in France in 2008 and married there in 2014. In 2016 she filed for divorce. In September 2021 she sold her stake in the winery to Tenute del Mondo, the wine arm of the Stoli Group. Court records put the deal at $64 million, paid in installments. In February 2022 Pitt sued her. He says they had agreed neither would sell without the other's consent. Jolie's side says no enforceable agreement required his approval. The divorce was finalized in December 2024. The winery case was not. In the video below, a news report walks through the latest turn in the fight. This year it moved to money records. Pitt wants Jolie's income records from 2017 to 2019, including back-end Hollywood deal money. She agreed to hand over 2020 and 2021 and calls the rest an overreach. In May a judge refused to force the release of 22 of her communications with advisers and publicists. In June a California appeals court revived Pitt's claims against Yuri Shefler of the Stoli Group, who guaranteed $39 million of the price. The panel ruled only that the case can go forward in California. It did not say who is right. According to Jolie's lawyers, Pitt is seeking $35 million in damages. No court has decided who is right. A trial is reportedly set for February 2027. Is this a business dispute over a sale, or a divorce that never ended?

Paris Jackson is not asking for $600 million for herself. She is asking a judge to put it into her father’s family trust, 17 years after he died. Paris Jackson is not asking for $600 million for herself. She is asking a Los Angeles judge to order it into her father's family trust, 17 years after he died. In her October 29 filing she says the estate held about $850 million in cash and equivalents at the end of 2024. After liabilities, she estimates about $600 million is distributable. Michael Jackson's will set up a trust for his three children. She says it has never been funded. Under the schedule she cites, the kids were meant to get trust income at 21, then a third of the principal at 30, half of the rest at 35 and the balance at 40. In the video below, E! News walks through the filing. The estate calls the claim that payments were withheld or cut "a complete fabrication." It says more than $200 million has already gone to or for the benefit of the beneficiaries, and that its tax dispute with the IRS is still not settled. None of this has been decided. The $600 million is her request and the $850 million is her figure. A hearing is set for December 4. If the estate has made billions, should the children's trust have been funded years ago, or is the estate right to wait?

Jay-Z led a $56 million deal for Tidal in 2015. Six years later Jack Dorsey's company agreed to pay $297 million for control of it. JAY-Z OWNS HIS MASTERS. HE ALSO LED A $56 MILLION DEAL FOR TIDAL. In 2004 he became president of Def Jam. Part of the job, he later said, was getting his masters reverted to him. They reportedly came back to him in 2014. He called it "the fight of my life." In 2015 he led a $56 million deal to buy Tidal. In March 2021 Square agreed to pay $297 million in cash and stock for control of it. Asked about selling his catalog, he said: "I want my kids to see my work."

$47.5 MILLION FOR THE BEATLES' SONGS Paul McCartney told Michael Jackson to get into music publishing. Jackson joked he would buy McCartney's songs one day. In 1985 he did. He paid a reported $47.5 million for ATV Music: 251 Beatles songs and about 4,000 others. McCartney later said it was like buying "the rug they're standing on." In 1995 Jackson sold half of ATV to Sony. In 2016 his estate sold its half for $750 million. In 2018 it sold a separate EMI stake for $287.5 million. That is over $1 billion from the publishing bets alone. In 2024 Sony reportedly paid at least $600 million for half of his own catalog.

WU-TANG MADE ONE COPY. IT SOLD FOR $2 MILLION. "Once Upon a Time in Shaolin" has 31 tracks, two discs and exactly one copy, in an engraved nickel-silver box. Commercial release is banned for 88 years, until 2103. In 2015 Martin Shkreli paid $2 million for it. In 2017 he was convicted of securities fraud. The government seized the album in 2018. In 2021 it sold again, reportedly for about $2.2M, to a Hong Kong shell company. That same year the crypto group PleasrDAO paid $4 million for it. RZA said it had been "in the wrong hands." It now sits in a New York vault.

Apple paid $3 billion for Beats, 7.5 times its previous biggest deal. Dr. Dre’s lawyer once told him to sell sneakers instead. DR. DRE SOLD HEADPHONES FOR $3 BILLION In May 2014 Apple confirmed it was buying Beats for $3 billion: $2.6B in cash and $400M in stock. It was Apple's biggest acquisition ever. The previous record was NeXT, at $400M. Dre was reportedly a 25% owner, about $480M after taxes. The headphone idea began when his lawyer suggested sneakers instead, per Wired. Weeks earlier he had called himself "the first billionaire in hip-hop." Forbes had him at $550M. At Apple's developer conference an exec called him on speaker. Dre asked: "What time should I show up for work?" Forbes added him to its billionaires list this March. Twelve years later.

Taylor Swift's first six albums were sold for an estimated $300 million in 2019. She wasn't part of the deal. In 2025 she got them back. Her label, Big Machine, owned the master recordings of her first six albums. June 2019: Big Machine was bought by Scooter Braun's Ithaca Holdings for an estimated $300 million. Billboard writes that her catalog was worth at least half of that, according to estimates at the time. Swift said she had not been offered a chance to buy her work outright. She could "earn" one album back for each new album she recorded for the label. November 2020: the masters were sold on to Shamrock Capital. One report says $300 million, another about $360 million. She wasn't involved in this sale either. So she did something else. She re-recorded the albums. April 2021: Fearless (Taylor's Version). November 2021: Red (Taylor's Version). 2023: Speak Now and 1989 (Taylor's Version). May 30, 2025: she announced she had bought the original masters back. The price was not disclosed. Billboard, citing sources, puts it at around $360 million. Another outlet says earlier rumors of $600 million to $1 billion were too high. Her letter: "All of the music I've ever made… now belongs to me." Billboard also estimates the firm in the middle made around $100 million in profit over the three years it owned the records. The masters sold twice. The artist got them back last. Was re-recording the smartest move in music business history, or the only one she had left? Save this for the next time someone says the artist owns the music.

50 Cent took shares in a water company as part of a deal. When Coca-Cola bought it, he reportedly made $100 million. The company was Glaceau, the maker of Vitaminwater. His deal began in October 2004, according to Trapital. He first wanted to invest in Vitaminwater alone. The Glaceau side was not initially on board, and the final deal came together later. It was not a normal endorsement fee. Reports say it was part of a broader sponsorship deal, paid out in Glaceau shares. Then Vitaminwater took off. AfroTech reports its sales grew from about $100 million to about $700 million within three years. May 2007: Coca-Cola buys Glaceau for $4.1 billion. His payout is usually given as about $100 million. Digital Music News calls it an estimate after taxes. Other outlets just say "reported." Nobody has published the contract or the size of his stake. A year later he told Forbes: "I was focused on the fact that $4.1 billion was made." And: "I think I can do a bigger deal in the future." The lesson isn't that he got famous and got paid. It's that he took part of the company instead of a flat fee. Save this the next time someone offers you a flat fee for something that could grow.

The UFC cost $2 million in 2001. Fifteen years later it sold for about $4 billion. The UFC cost $2 million in 2001. Fifteen years later it sold for about $4 billion. In January 2001, casino owners Frank and Lorenzo Fertitta bought the UFC from Bob Meyrowitz, whose company owned it at the time. They put Dana White in as president, with a reported 9% stake. For years it did not pay off. By 2004 the Fertittas had put over $40 million into the company without making a real profit. Then they paid for a reality show themselves, because TV networks refused to. The Ultimate Fighter, 2004. Its finale between Stephan Bonnar and Forrest Griffin is credited with saving the UFC. 2006: UFC 66 passes a million pay-per-view buys. 2008: Forbes values the company at $1.1 billion. 2015: gross revenue reaches $600 million. July 2016: the UFC sells to a group led by WME-IMG for about $4 billion. White owned 9% when it sold, and he kept a stake in the new company. 9% of $4 billion is about $360 million on paper. That is a rough figure, not a payout. In 2023 the UFC merged with WWE into one public company, TKO. White became UFC's CEO. By 2025 Forbes put his net worth at over $600 million. The money was never in the $2 million purchase. It was in surviving the years when it lost money. Was it vision, or the one bet that happened to work out? Save this for the next time someone calls a business a bad idea.

TLC sold over 10 million copies of "CrazySexyCool." The members say they got about $50,000 each. In July 1995 the group filed for Chapter 11 bankruptcy, listing $3.5 million in debts. How it happened, as the members and reports tell it: 1991: TLC signs with LaFace Records and a management company run by the singer Pebbles. The contract reportedly paid the trio 56 cents per album sold, split three ways. The label and the management company charged back recording, video, travel and promotion costs. 1994: "CrazySexyCool" comes out. It reaches diamond status in the US, the only album by a female group to do so, according to Beat. July 3, 1995: TLC files for bankruptcy. Chilli later said that when they filed, they were in court and Arista wanted their plaques back. T-Boz said: "We gave them away to everybody in the projects." In 1996 they got out of the management contract and renegotiated with the label. The money part: T-Boz said in 2009 that the album made $75 million and the three were paid $50,000 each. Nobody has published the contract, so these are the members' numbers. Selling 10 million copies and filing for bankruptcy in the same year. Save this the next time someone says a hit record means a rich artist.

In January 2019 Ariana Grande released "7 Rings." Spotify reported it broke the 24-hour streaming record: 14,966,544 streams in one day. Then the money question came up. "7 Rings" interpolates "My Favorite Things," a song from the 1959 musical The Sound of Music, written by Richard Rodgers and Oscar Hammerstein II. Their catalog is owned by Concord. It bought it in 2017. According to The New York Times, Concord asked for 90% of the royalties on the new song. Grande's team agreed. Her label, Republic, reportedly did not try to negotiate the rate. Why that rate? Concord's publishing executive told the Times the song "wouldn't exist in its current form" without "My Favorite Things." The song has 10 credited writers. One of them, as far as the reports say, is a 60-year-old musical. What nobody has made public is the contract. Every report traces back to the same Times story, and I could not find the split in writing. So what we have is a reported 90%, not a confirmed one. What it shows is simple. You can have the biggest streaming day of the year and still share most of the song's royalties with the writers of a 1959 musical. Save this for the next time someone says the artist keeps everything.

Watch how Dave Grohl talks about Courtney Love in this old interview. "She's very outspoken and she's not willing to cooperate with the establishment. That's one of the things all of us really respect her for." Same people. Same band. Different decade. In 1997 Nirvana's business went into one company: Nirvana L.L.C. Three members. Love, Novoselic, Grohl. In 2001 it split. Love sued, saying Nirvana was Kurt's band and the other two were little more than sidemen. In December Novoselic and Grohl filed their own suit over control of the catalog. A court then froze two things: the song "You Know You're Right" and a 45-track box set. The money that followed: Love reportedly made at least $9 million from the fight: about $4 million from the deal and $5 million from publishing royalties. In 2006 she reportedly sold a 25% stake in her share of the catalog. The rumored price was $50 million. Now it's back in the news. Love says she signed a paper giving Dave and Krist money "in perpetuity" and that she is "unsigning it." Her words, not a court's finding. The music was always shared. The question was who controlled it. Save this for the next time someone says a band is just about the music.

Daymond John did not have the money to dress the stars, so he dressed the men standing next to them. He made 50 shirts in sizes 5X and 6X and gave them away. Not to rappers. To their bodyguards. In the video below, he explains why it worked. The bodyguards stood right in front of LL Cool J, Run-D.M.C. and Salt-N-Pepa, so the shirts were in every shot. And the men wearing them had almost nothing to choose from: a plain white or black shirt from a big and tall store, or something custom. Then the artists started asking where the clothes came from. By his own account, FUBU began with $40. A $100,000 mortgage on his mother's house kept it going. At its peak, NBC News reports, the brand netted $350 million in sales through 5,000 stores. The shirts are not the part worth stealing. The logic is. When you cannot reach the person who has the attention, find the person standing next to them and solve a real problem for them. Somewhere tonight, someone with $40 and a sewing machine is looking at a room full of people who already have the crowd. Save this for the day you need an idea that costs almost nothing.

HIS PARENTS PUT IN $245,573. HE TOLD THEM THE ODDS WERE 30%. In 1994, Jeff Bezos started an online bookstore. Then he went looking for money, and he did not oversell it. His parents put in $245,573 in 1995, according to Amazon's 1997 prospectus. In the video below, Bezos explains what he told his early investors: "I thought there was a 30% chance of success, by which I meant getting your money back." His father's first question about the company, Bezos has joked: "What's the Internet?" Most pitches start with the upside. His started with the odds. Takeaway: tell people the real odds. The ones who still say yes are the ones worth having. Would you invest in a founder who tells you it is 30%?

50 SHIRTS FOR BODYGUARDS. LATER, $350 MILLION IN SALES. Daymond John did not have the money to buy shirts for everyone who might wear his brand. So he made 50 shirts, all sizes 5X and 6X, and gave them away. Not to the stars. To their bodyguards. In the video below, he explains the logic. Those men stood right in front of LL Cool J, Run-D.M.C. and Salt-N-Pepa. Their clothing options were a plain white shirt from a big and tall store or something custom. "The artists started asking for the clothes," he says, because they saw the guards wearing them. FUBU began with $40, by his own account. His mother took a $100,000 mortgage on her house to keep it going. At its peak, the brand reached $350 million in sales through 5,000 stores. Today people call it influencer seeding. In the early 90s, it was 50 shirts and a red rope. Takeaway: when you can't reach the person with the money, dress the person standing next to them. Which hustle would you try with only 50 shirts?