Five years after his death, the legacy of Viacom/CBS mogul Sumner Redstone continues to make headlines. His daughter, Shari Redstone, is currently fighting to close an $8 billion sale of Paramount Global to David Ellison's Skydance Media. The deal would help the Redstone family pay off hundreds of millions in debt and preserve their control through preferred shares. But the merger has hit serious turbulence due to a $20 billion lawsuit filed by President Trump, who claims CBS' "60 Minutes" deceptively edited an interview with Kamala Harris.
The lawsuit has triggered an FCC review and sparked concerns from lawmakers that a potential settlement with Trump could violate federal bribery laws. Paramount executives have resigned over the controversy, and the deal's future remains uncertain. If it collapses, Paramount will owe Skydance a $400 million breakup fee.
But long before Shari Redstone was navigating boardroom battles, her father was making headlines of a very different kind… by spending hundreds of millions of dollars on ex-girlfriends, mistresses, and brief flings…
Sumner Redstone lived a fascinating life. His father started as a delivery driver and later used his earnings from bootlegging during Prohibition to launch a legitimate liquor distribution company. That business became lucrative enough to bankroll early investments in nightclubs and drive-in movie theaters. After earning a law degree and working as a federal antitrust attorney, Sumner joined the family business in his early 30s and soon took over. He rebranded it as National Amusements and began expanding a chain of drive-ins across the country.
Redstone funneled those profits into the media sector. His first major move came in 1987, when he bought Viacom for $3.7 billion. He later merged it with Blockbuster and used the combined company to acquire Paramount for $10 billion. In 1999, he spent a then-record $37 billion to acquire CBS.
At its peak, Redstone's 80% stake in National Amusements was worth $6 billion. When he died in 2020 at the age of 97, he was worth $2.6 billion.
But Redstone's exploits weren't confined to boardrooms and balance sheets. He was legendary for his extravagant spending on women—lavishing gifts, cash, and property on a long line of ex-girlfriends, flings, and acquaintances.
Sumner was married twice. Once for over 50 years. The second time was to a woman nearly four decades his junior. Apparently, along the way, he had many, many trysts.
We learned about some of these trysts thanks to a 2016 lawsuit involving an ex-girlfriend named Sydney Holland. Redstone's family members launched a lawsuit against Holland and a housekeeper, accusing them of emotionally abusing Sumner while also tricking him into giving them over $150 million in gifts over a five-year period.
In Holland's response, she claimed Redstone had a decades-long history of giving girlfriends extremely lavish gifts and payments.
Holland testified that the sex-starved nonagenarian once gave a flight attendant who worked on the CBS corporate jet $18 million. He then proceeded to have sex with the flight attendant's sister. He reportedly gave the sister $6 million.
According to Sydney Holland, the sisters were just two of at least 11 women that Redstone showered with cash after trysts. From her court filing:
"Redstone gave tens of millions of dollars to various other women, who he had no intention of marrying and was not in love with, at the time, he was engaged to marry Sydney. Women who did nothing more than provide sexual favors."
Here's Sumner and Sydney pictured together:
Sumner Redstone and Sydney Holland (Frederick M. Brown/Getty Images)
Holland met Redstone in the fall of 2010 when they were set up by "The Millionaire Matchmaker" Patti Stanger. Their courtship involved expensive dinners out and long drives down the Pacific Coast Highway. Soon, Holland was Redstone's lover and caregiver. In exchange, he agreed to take care of her financially for the rest of her life.
According to Holland's court filings, Redstone required that she be home for lunch and dinner with him seven days a week. She was also required to go to bed when he wanted to, whether or not she was tired. In exchange, Redstone showered her with Hermes bags, jewelry, art, cash, and weekly bouquets of her favorite flowers.
But when Redstone found out about a short-lived affair Holland had, he kicked her out of his mansion, cut her off financially, and removed her from his trust.
Holland sued to secure a reasonable monthly support, plus an amendment to Redstone's trust reinstating her as a beneficiary.
Holland also accused Redstone's daughter, Shari Redstone, of blocking Holland from her father's life. Sumner Redstone's attorneys called Holland's claims a work of fiction.
Here are some additional notable claims from the filing:
- Sumner allegedly gave one of his mistresses, an aspiring reality TV show producer, $21 million
- He gave another woman, also met through Patti Stranger, $10-$11 million
- He gave another mistress $7 million
- He gave a friend of his grandson's girlfriend a job at Showtime and $6 million
- He gave another mistress $1.5 million
- He paid for a college student's tuition at the University of California while also paying her an undisclosed amount
- Holland claims that there are "many other women who he gave tens of millions of dollars to"
- Holland also drops not-so-subtle hints that the billionaire's sexual predilections are not conventional. The court documents state that there were "many other acts committed by Redstone and uncomfortable requests he made of Sydney that will not be detailed here."
If you add all these alleged payments up and combine with the $150 million Sydney Holland and a housekeeper reportedly were given by Sumner, we're talking about AT LEAST $220 million in payments to girlfriends and hook-ups. This doesn't include "undisclosed amounts" or the "tens of millions" allegedly paid to other women.
Insane. Is it just me, or wouldn't it have been A LOT cheaper to pay for a few of the most expensive call-girls on the planet to be available 24-7?
But hey. When you're a billionaire, you can do whatever you want with your money!