Sumner Redstone paid millions to mistresses and others who gave him 'sexual favors,' legal filing says

Sumner Redstone and Sydney Holland in 2014
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That must have been a hell of a flight.

Media titan Sumner Redstone gave out many millions of dollars to multiple women — mistresses, a flight attendant and that attendant's sister — according to legal documents filed Monday by his 45-year-old ex-girlfriend.

The CBS corporate jet flight attendant alone got $18 million — and her sister, whom Redstone allegedly bedded, received a cool $6 million from the randy billionaire, court filings claim.

The explosive allegations by former Redstone paramour Sydney Holland were accompanied by a warning that she "may be forced" to seek testimony from the 93-year-old mogul's celebrity friends as well as from executives from Viacom and CBS, whose shares he controls, to substantiate her salacious claims.

Redstone's legal team, in an emailed statement to CNBC, said, "Ms. Holland's cross-complaint is a work of fiction punctuated by not-so-subtle threats of extortion and an overwhelming stench of greed."

In her Los Angeles Superior Court filing, Holland said 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" Holland.

"Women who did nothing more than provide sexual favors," the filing said.

Her allegations were made in a response to a lawsuit by Redstone accusing Holland and one of his other ex-girlfriends, Manuela Herzer, of conspiring to emotionally manipulate and abuse him so that he would give them gifts totaling $150 million over the years.

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The filing said it "makes no sense" that Redstone's lawsuit only names Holland and Herzer as defendants when "Redstone knows that there were (and possibly still are) many other women who he gave tens of millions of dollars to (during this same time-period that he alleges Sydney and Herzer had 'total control' of his life)."

Holland also filed a cross-complaint against Redstone alleging breach of contract — both "oral" and "implied in fact." She says that in exchange for agreeing to make Redstone "the center of her universe" during their time together, he "promised to take care of her financially for the rest of her life."

The filing asks that Redstone be ordered to pay Holland "a reasonable sum per month" to support her and her young daughters.

Sydney Holland
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Her filing said that for "five years, Sydney and Plaintiff Sumner Redstone ... enjoyed a loving, romantic relationship," which began in the fall of 2010 after the media baron "hired Patti Stanger, 'The Millionaire Matchmaker' to find him a girlfriend who was not only young and beautiful, but also intelligent, funny, and who shared Redstone's Jewish faith."

Holland's filing said that "as a result of this lawsuit" against her and Herzer, "the lurid nature of these relationships and the significant amounts of money that Redstone paid to these [other] women are directly at issue."

"Sydney may be forced to disclose their identities and call Redstone's celebrity friends and Viacom and CBS executives as witnesses," the filing said in her answer to Redstone's suit.

The filing also said that it was known to Redstone's advisors, attorneys, doctors, friends and staff, as well as to Redstone's "close friend and CBS executive officer" CEO Leslie Moonves that Redstone had given Holland about 1.5 percent of his net worth over a five-year span.

Holland's filing then offered a list of unidentified women and the staggering amounts they received from Redstone "just while Sydney was living with Redstone."

  • "He gave one mistress — an aspiring reality show producer — approximately $21 million."
  • "He gave a flight attendant on the CBS corporate jet just approximately $18 million."
  • "He later slept with her sister, who he gave approximately $6 million."
  • "He gave another woman who he had formally met through Patti Stanger [the matchmaker] $10-11 million."
  • "He gave another mistress — who claimed to be a model — over $7 million."
  • "He gave a friend of his grandson's girlfriend a job at Showtime and approximately $6 million."
  • "He gave another mistress approximately $1.5 million."
  • "He gave an ex-fiancee and Paramount employee an undisclosed amount."
  • "He paid for a college student's tuition at the University of Southern California and gave her an undisclosed amount."

"Despite Redstone's infidelity (and many other acts committed by Redstone and uncomfortable requests he made of Sydney that will not be detailed here) Redstone repeatedly told Sydney that she was the only woman that he truly loved," the cross-complaint said. "She believed him."

But, Holland's filing adds, "unfortunately ... after years of a monogamous commitment to Redstone (with none in return) and living in a very controlled environment, Sydney succumbed to a short-lived affair."

After she confessed her "indiscretion to Redstone," he "broke off their engagement and asked Sydney to move out."

"He did not, however, ask her to return the gifts or money that he had given her," the filing said.

In their statement, Redstone's lawyers said: "The critical witnesses will not be Mr. Redstone's 'celebrity friends' but instead the nurses and household staff members who, unlike Ms. Holland, were by his side day and night."

Redstone's lawyers added: "It will be for the jury to weigh the contemporaneous notes and trial testimony of those disinterested witnesses against Ms. Holland's narcissistic false narrative. In the end, we are confident that justice will be done."

Holland's filings are laden with photographs showing her smiling at Redstone's side. Several show Redstone holding Holland's baby daughter, and her filing said, "He helped Sydney conceive her daughter and was by Sydney's side when her daughter was born in their home."

Another photo shows a 9-carat canary yellow engagement ring that Redstone allegedly used to propose to Holland in 2011, as well as handwritten notes he left for her.

"I will always love you. You can always depend on me. Love, Sumner," said one such note replicated in the filing.

The filing said that, "While Sydney could not match Redstone's financial generosity, her love was no less deep, and they enjoyed a mutually beneficial union through their love, support and care for one another."

Holland, in her legal filings, described a romantic courtship after she and Redstone met through the celebrity matchmaker Stanger, one in which "they took long drives down the Malibu coast, listening to Tony Bennett and Frank Sinatra."

"They went to restaurants and shared Redstone's favorite dessert, chocolate mousse," the filing said. "Before they knew it, they were spending nearly every waking moment with each other."

"While Sydney could not match Redstone's financial generosity, her love was no less deep, and they enjoyed a mutually beneficial union through their love, support, and care for each other," the filing said.