Sumner Redstone in Love: The Cringey Sexcapades of a Horny Billionaire

Stanger was convinced that despite their age difference and Holland’s obvious financial motive, Holland was in love with Sumner. Stanger had known plenty of women who were romantically drawn to much older men. Holland took Stanger’s advice to heart. She served at Sumner’s beck and call. Soon she was indispensable.

When Sumner asked Holland to move in with him, she did, taking on the roles of wife, secretary, business manager, and, increasingly, nurse. She redecorated the mansion. She arranged visits there with Sumner’s longtime friends Charlie Rose, Michael Milken, and Sherry Lansing, not to mention the women she imported for his sexual gratification. She oversaw his dealings with CBS and Viacom, organized a CBS board meeting at the house, arranged his Sunday movie screenings, and got him to his dentist and doctor appointments.

Sumner made many demands on Holland, all of which she maintained she met: that she be present for every lunch and dinner with him; that she go to sleep when he did (even though this was much earlier than she preferred); that she not take overnight trips without him; that she stop seeing her friends. Sumner, however, “could do whatever he wanted.”

Holland was hardly the only woman in Sumner’s life. He was still courting Malia Andelin. And he had continued seeing and confiding in his old flame Manuela Herzer. Holland may have been first among equals, but she and Herzer had forged an alliance. While Herzer’s house was being renovated in 2013 at Sumner’s expense, Sumner invited Herzer and her daughter Kathrine to live with him and Holland.  

With Herzer’s arrival, the atmosphere changed dramatically inside Sumner’s mansion. Surveillance cameras were installed throughout the Redstone property, and nurses and staff were subjected to lie detector tests. Anyone deemed disloyal to Holland or Herzer was fired. As the women consolidated their control over the mansion, its staff, and Sumner himself, the number of people with unrestricted access to him dwindled. This included his immediate family—Shari and the grandchildren he so doted upon. Holland or Herzer sat in on all their visits or had staff members present who would report on their conversations. Most of the family’s calls to Sumner were also blocked, though Holland and Herzer then told Sumner his family never called. According to Jagiello, “Sydney and Manuela reacted angrily when they learned that a nurse or member of the household staff had put those calls through and made clear that it was a fireable offense.”

In what Jagiello described as a “constant bombardment,” Holland and Herzer “regularly disparaged Shari to Mr. Redstone, telling him that she was a liar, was only after his money, and was defying his wishes in both personal and business matters.”

Holland and Herzer seemed to tolerate Sumner’s continuing infatuation with Malia Andelin, who still showed up at the mansion nearly every week notwithstanding Sumner’s purported engagement to Holland. Sumner called her constantly, sometimes multiple times a day, leaving long messages saying he loved her. “I am sorry I am crying,” he told her. “Every time I think of you I cry. I can’t help it. And remember, if you ever need anything at all—money, advice, whatever—you call me. I will always be there for you.” He called her “my one and only.”

Andelin tolerated this, but she had no romantic feelings for Sumner. Although Sumner often made lewd and inappropriate sexual comments, Andelin doubted he was even physically capable of sex in any conventional sense. Andelin felt it was more that he wanted his cronies, like Bob Evans and Larry King, to think he was sleeping with attractive young women. Andelin felt Holland and Herzer were jealous of Sumner’s affection for her but knew there was little they could do about it. Her presence also gave them what may have been some welcome evenings off from catering to Sumner’s whims. The two women even helped Sumner pick out expensive gifts for Andelin, like diamond earrings and a Rolex watch, sometimes inflating the tab by adding purchases of clothing and jewelry for themselves.

Herzer counseled Andelin that she could be asking Sumner for much more. Turning down his marriage proposal years earlier was the biggest mistake of her life, Herzer confided.

Andelin had never asked Sumner for money and initially resisted when Sumner said he wanted to help buy her a house. But she gave in after he said he’d choose one for her if she didn’t. She ended up with a $2.65 million cottage in exclusive Corona del Mar, not far from her home in Laguna Beach. As time went on, Sumner’s gifts to Andelin grew more extravagant. Six‑ and even seven‑figure deposits of cash and CBS and Viacom stock started showing up in her account. 

Andelin was well aware of what other people thought of her and Sumner’s relationship. She didn’t like it. She hated the idea that people thought of her as another Holland or Herzer. Still, she accepted the money and gifts. The more she did, the lower her self‑esteem sank. Sometimes she wondered: Was she experiencing a version of Stockholm syndrome, in which a victim of abuse develops an attachment to the perpetrator? For all Sumner’s faults, over their years together Andelin developed some compassion for him. She felt he was fundamentally lonely and deeply insecure.

She also rationalized the arrangement by thinking of it as her job. However “foul‑mouthed and crude” he could be, as she put it, she considered Sumner a mentor, a brilliant businessman from whom she could learn a great deal. And perhaps she could change Sumner for the better.

In this she had her work cut out for her. At a dinner at e. baldi restaurant in Beverly Hills, Sumner complained that the director Steven Spielberg had been pushing him to be nicer about Barack Obama. Obama was wildly popular with the Hollywood elite, but Sumner was no fan of the president. “Obama is a . . . ,” Sumner loudly said, using the N‑word.

Andelin was horrified. “You can’t say that word!” she exclaimed. “It’s a joke,” he insisted.

“You still can’t say it, especially where people might hear you.”

At one point Sumner asked Andelin if she thought he was a “horrible person.” “If I was your age and we met, would you be friends with me?” he asked. “Is there a chance you would even like me if I were your age?”

Andelin didn’t want to hurt his feelings, but, following Shari’s advice, she was honest. “I don’t know,” she said. “You’re not very nice.”

Sumner started to cry.

Excerpted from UNSCRIPTED: The Epic Battle for a Media Empire and the Redstone Family Legacy by James B. Stewart and Rachel Abrams, to be published on February 14, 2023 by Penguin Press. Copyright © 2023 by James B. Stewart and Rachel Abrams.

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