Behind the biggest celebrity fortunes are the deals that made them — brand sales, catalog buybacks, franchise exits and equity stakes worth hundreds of millions or more. This page ranks the biggest business deals among the stars profiled on Net Worth VIP, largest first. Every entry links to a fully sourced profile.
| Celebrity | Date | Amount | Net worth (2026) | Details |
|---|---|---|---|---|
| Mark Cuban | 1999-04 | $5.7B | $6B | Sold the streaming company he co-founded to Yahoo for $5.7 billion in stock, then hedged the shares before the dot-com crash. source |
| Mark Cuban | 2023-12 | $2B | $6B | Sold his majority stake to the Adelson and Dumont families at a $3.5 billion valuation (about $2 billion pre-tax for his share), keeping 27%. source |
| Dr. Dre | 2014-05 | $750M | $1B | Apple bought Beats for $3 billion; Dre's roughly 25% stake was worth about $750 million pre-tax, the deal that made his fortune. source |
| Jay-Z | 2023-02 | $750M | $2.8B | Settled a legal dispute and sold most of his D'Usse stake to Bacardi; his payout was reported around $750 million. source |
| Taylor Swift | 2025-05 | $360M | $2B | Repurchased her first six albums' masters from Shamrock Capital for a reported ~$360 million, finally owning her entire catalog. source |
| Jay-Z | 2021-03 | $302M | $2.8B | Jack Dorsey's Square (now Block) acquired a majority of the streaming service for a reported $302 million. source |
| Dr. Dre | 2023 | $200M | $1B | Sold royalties and masters for a reported ~$200 million. source |
| Neil Diamond | 2022-02 | $150M | $300M | Sold his complete song catalog and all master recordings to Universal Music Group; terms undisclosed but estimated ~$145 million (Billboard) to over $200 million. source |
| Conor McGregor | 2021-04 | $150M | $200M | Sold his stake in Proper No. Twelve; his personal share is reported between $130 million and $200 million pre-tax. source |
| Tiger Woods | 2024-06 | $100M | $1.4B | Received a reported ~$100 million equity grant, the largest of the PGA Tour player loyalty grants. source |
| Oprah Winfrey | 2015-10 | $43.2M | $3.4B | Bought a 10% stake for $43.2 million and joined the board; she donated her remaining shares in 2024. source |
| RZA | 2021-07 | $4M | $30M | The single-copy Wu-Tang album, seized from Martin Shkreli, was acquired by the collective PleasrDAO for $4 million. source |
| Steven Spielberg | 1994 | $7.1B | Co-founded the DreamWorks studio with Jeffrey Katzenberg and David Geffen, adding studio ownership to his film wealth. source | |
| Oprah Winfrey | 2020-12 | $3.4B | As Discovery raised its OWN stake to 95%, she swapped most of Harpo's interest for $35 million-plus in Discovery (now Warner Bros. Discovery) shares. source | |
| Tiger Woods | 2024-01 | $1.4B | His Nike deal, worth an estimated $660-700 million over 27 years, came to an end; he later launched the Sun Day Red brand with TaylorMade. source | |
| Cristiano Ronaldo | 2025-06 | $1.3B | Renewed through 2027 in a deal reported to pay over $200 million a year, tax-free, keeping him the world's highest-paid athlete. source | |
| Jay-Z | 2021-02 | $2.8B | Moet Hennessy (LVMH) bought half of his champagne brand, which had been valued around $640 million. source | |
| Jeannie Mai | 2021-03 | $2M | Married rapper Jeezy; a prenuptial agreement was signed the day before the wedding. source |
Figures are reported estimates aggregated from the sources cited in each row; deal terms are often private, so amounts can vary by source. See our methodology. Related: the biggest single paydays and celebrity bankruptcies.