Viacom Billionaire Sumner Redstone Paid An Insane Amount Of Money To Ex Girlfriends And Hookups During His Lifetime

Along the way, Sumner’s 80% stake in the family holding company National Amusements hit an all-time high of $6 billion. He was worth $2.6 billion at the time of his death in 2020. As it turns out, Sumner was legendary in both the boardroom AND the bedroom. He was married twice. Once for over 50 years. The second time to a woman nearly four decades his junior. Apparently, all along the way he had 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 on the CBS corporate jet $18 million. He then also had sex with her sister, whom he gave $6 million. The sisters were just two of at least 11 women that Redstone showered with cash, according to  Sydney Holland. “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.” the Los Angeles Superior Court filing stated. Here’s Sumner and Sydney pictured together: 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 the filing, Redstone required that Holland 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 and cut her off financially as well as had her removed from his trust. Holland is seeking a reasonable sum per month, plus an amendment to Redstone’s personal trust reinstating her as a beneficiary. Holland also accuses Redstone’s daughter Shari of blocking Holland from her father’s life. Sumner Redstone’s attorneys call Holland’s claims a work of fiction. 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!