Money Talks


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

The elderly media titan flexed his MTV ownership, rang his grandson at 3 a.m. for hookups with new women, and rewarded companions with stock options and TV shows. A wild exclusive excerpt from the new book Unscripted.


In 2008 Malia Andelin, a twenty‑six‑year‑old makeup artist living in Laguna Beach, was, like so many Americans at the time, supplementing her income by buying and flipping real estate using borrowed money. Then the financial crisis struck, credit abruptly evaporated, and that was the end of that. Andelin was looking for another source of income when a friend recommended she try working as a flight attendant on a private jet. Part of her training was a self‑defense course, where she met two pilots who recommended she work with them at the aviation company that staffed the CBS and Viacom planes.

Slim and blond, Andelin had grown up in Utah, the youngest of eight children in a straitlaced Mormon family. She’d never flown professionally, but she was willing to give it a try. On her first outing one of her passengers was Robert Downey Jr.

Andelin liked the work and seemed to have an aptitude for it. Inevitably the day came when Sumner Redstone was on board. In late November, little more than a month after he filed for divorce from Paula, Sumner was flying from New York back to Van Nuys Airport outside Los Angeles with his friend Arnold Kopelson, a producer and CBS board member, and his wife, Anne. While waiting for takeoff, Andelin went into the passenger cabin and asked Sumner if she could help him with his seat belt. 

“Who the fuck are you?” he asked.

“Sumner, stop,” Anne Kopelson interjected.

Andelin hardly knew how to respond. “I’m Malia,” she said. “I work on the plane.” She reminded him she’d flown with him once before.

“I’d remember a pretty face like yours,” he replied.

That angered her. “Who the fuck are you?” she said, and left the cabin.

That she could give as good as she got seemed to drive Sumner wild. He buzzed for her constantly once they were in the air.

“I hear women like to be spanked,” Sumner told her at one point. “Do you like to be spanked?”

Anne Kopelson tried in vain to silence him. Arnold said nothing.

“Please don’t sue me for sexual harassment,” Sumner told Andelin, and then laughed.

Sumner pelted Andelin with inappropriate comments for the rest of the flight, and she grew increasingly upset. He asked repeatedly for her address and phone number. She refused.

Available from Amazon and Bookshop.

Available from Amazon and Bookshop.

The pilots were aghast but not surprised—Sumner had made a habit of harassing women on the corporate jets and then getting them fired. After the plane landed, one of the pilots pulled Andelin aside.

“I’m probably not going to see you again,” he said. “I know how he is. We all know how he is.”

Despite her refusal, Sumner had no trouble getting Andelin’s phone number, presumably from the aviation company. He called incessantly— so often she turned off her phone. He left messages proposing they have dinner to discuss the menu on the corporate plane. She ignored him. Meanwhile, she wasn’t getting any assignments despite her persistent requests for more work. Sumner seemed to be dangling the prospect of getting her job back if she’d join him for dinner.

“Some say I created Mission: Impossible, and some say that this mission is impossible,” Sumner told her in one voice message. “But I made this mission possible. And I know that you’re risk averse and you wouldn’t talk to me on the plane, but I know that if you called me back and you were a risk‑taker, this call could perhaps change your life.”

The message infuriated Andelin. How dare he leave her suggestive voice mails after she’d refused to give him her number and he’d blacklisted her from working on the plane? She called him and left a message. “Who do you think you are? This is not okay. I just want to know when I can have my job back.”

Sumner’s driver finally showed up at her house. Would she have dinner with Sumner? Just once?

Nothing Andelin had done or said had deterred Sumner. She worried: given his enormous wealth and power, to what lengths might he go? Perhaps it would be easier to accept his invitation, at least once. Maybe she’d get her job back.

She eventually agreed to have dinner with Sumner. Something told her she’d come to regret it.

From the Zagat guide Sumner picked a restaurant in Newport Beach, not far from where Andelin lived. When the day arrived, Sumner picked Andelin up and had his driver take them there. She rarely drank alcohol, but that evening she sipped a glass of wine to calm her nerves.

After they left the restaurant, Andelin got in the back seat and Sumner slid in next to her. But instead of taking his seat in front, the driver lingered outside, leaving them alone in the car. Suddenly Sumner lunged at her and tried to get his hand under her blouse. Andelin pushed him away and managed to open the door and get out. She was in shock. She later didn’t remember how she got home.

The next day Sumner called and sent Andelin an email, which she ignored. Then his driver showed up and told her Sumner wanted to apologize in person. Various thoughts crossed her mind. Her first reaction was that she never wanted to see him again. But as she wrote in her journal at the time, Sumner had so much money and power he’d crush her eventually. She didn’t really feel she had a choice.

She reluctantly agreed to see him again.

Carlos Martinez, Sumner’s house manager for over ten years, greeted her when she arrived at Sumner’s mansion. He tried to reassure her. “There’s nothing to be afraid of,” he said. “I’m here. You’re not alone. You’re going to be okay. He just wants to give you the world.” But while Sumner was showing her his fish tank, she felt sick and thought she might faint.

Somehow she got through the evening. The next time Sumner invited her, she accepted. After one of her subsequent visits, Martinez gave her a check for $20,000, the amount, he said, she would have been paid had she worked on the jet that month. 

She didn’t get any more work as a flight attendant. After about a month, Sumner told her there was no need for her to work on the plane. Instead, she could accompany him to dinners and join him on the red carpet at the many Hollywood premieres, galas, and benefits he attended.

Soon Andelin was a fixture at Sumner’s mansion, usually having dinner with him every week. As he did with others, Sumner often disparaged his children, Brent and Shari, when confiding in Andelin. Occasionally she had to sit through father‑daughter visits, which she found awkward and tense. After a dinner with Sumner and Shari, Andelin shared a car with Shari, who cried during the trip.

One day Andelin was at the mansion when Shari brought Sumner some homemade biscotti. As Shari was leaving, she pulled Andelin aside. “You’re so sweet,” Shari told her. “I don’t know what your relationship is with my dad, but one thing you need to know: always speak your mind to him. Never back down, and always say how you feel.”

Andelin felt Shari was one of the few people around Sumner who was nice to her.

At its annual global conference in April 2009, the Milken Institute paired celebrity CNN host and interviewer Larry King with eighty‑five‑year‑old (about to turn eighty‑six) Sumner. King titled his “conversation” with Sumner for “If You Could Live Forever ….  ”

The room at the Beverly Hilton was packed. Clad in a navy suit and an open‑necked blue shirt, Sumner began by asserting, “I have the vital statistics of a twenty‑year‑old,” a claim somewhat belied by the substantial paunch visible at his waist. “Even twenty‑year‑old men get older. Not me. My doctor says I’m the only man who’s reversed it. I eat and drink every antioxidant known to man. I exercise fifty minutes every day.”

However amusing the audience may have found Sumner’s claim to immortality, it reflected something more than just vanity. He had confided in Andelin that the prospect of death terrified him because he’d face judgment and punishment for his many sins—a reckoning that thus far he’d escaped in life. 

“How old are you?” King asked.

“Sixty‑five,” Sumner replied. The audience laughed.

“Realistically,” King pressed him, “how old are you?” 

“Sixty‑five,” he insisted.

Sumner said he felt better than he had at age twenty. 

“You have not slowed down sexually?” King asked. “No, I haven’t.”

If anything, that appeared to be an understatement. Even as he courted Andelin with money, gifts, and attention, he was dating Rohini Singh, who at age nineteen had been the subject of an embarrassingly detailed 2001 Los Angeles Magazine cover story: “Hooking Up: Sex, Status and the Tribal Rituals of Young Hollywood.” At Sumner’s insistence, CBS’s Showtime hired Singh that summer despite a hiring freeze at the cable network. Sumner showered her with Viacom stock, as well as a reported $18 million in payments.

The same year Sumner also started seeing Terry Holbrook, a brunette former Ford model and Houston Oilers cheerleader. Sumner bought her a $2.5 million house and paid for her stable of show horses. Manuela Herzer, who’d become one of Redstone’s live-in companions, maintained that Sumner paid Holbrook $4,500 a month in cash and those and other payments eventually amounted to $7 million. He also made Holbrook a beneficiary of his trust.

Over the years Sumner amended his trust more than forty times to add and remove numerous beneficiaries, many of them women he dated. Dauman, who as a co-trustee of Sumner’s trust was aware of many of the gifts, acknowledged that “several” women received over $20 million each, “a lot” of women received over $10 million, and “many, many” women received over $1 million.

In the spring of 2010 The Daily Beast’s Peter Lauria reported Sumner was dining at Dan Tana’s with Les Moonves, his wife Julie Chen Moonves,  and a “tall, tan, fembot‑like blonde, young enough to be his granddaughter.” The “fembot” was Heather Naylor, Sumner’s latest fixation and the lead singer of a largely unknown girl group called the Electric Barbarellas. Sumner was pushing a reluctant Viacom‑owned MTV to develop a reality series featuring the group’s quest for stardom, and he also wanted CBS to promote them.

Heather Naylor with The Electric Barabellas at the 2011 MTV Movie Awards.
Heather Naylor (center) with The Electric Barabellas at the 2011 MTV Movie Awards.

Moonves dreaded these requests, but Sumner was his boss. Clad in satin hot pants and singing wildly off pitch, the Barbarellas made their CBS network debut on The Late Late Show with Craig Ferguson on March 27, 2011. The operative word was late: their appearance came close to the end of the show at 1:30 a.m., when Moonves could only hope few people would be watching.

Lauria reported that Sumner spent half a million dollars flying the Barbarellas to New York for MTV auditions and had pushed the reality series into development over MTV executives’ strident objections. They told Lauria the show was “unwatchable and the music just as bad.” Even Dauman tried to kill the project, but “I won’t be defied,” Sumner insisted. 

The mildly embarrassing episode might have remained largely confined to Hollywood insiders, had Sumner not picked up the phone and called Lauria—not to deny the story but to try to unmask Lauria’s Viacom source, who Sumner speculated was a “young, male executive” who worked for MTV.

“You will be thoroughly protected,” Sumner assured Lauria in the call, which Lauria taped in its entirety and the Beast made available to the public. “We’re not going to hurt this guy. We just want to sit him down and find out why he did what he did. You will not in any way be revealed. You will be well‑rewarded and well‑protected.”

Lauria refused to disclose his source and instead turned the en‑ counter into another story, which, thanks to Sumner’s direct involvement, got even more media attention. New York Times media columnist David Carr called the tape “a classic, a must‑hear document of mogul prerogative in full cry.”

When Viacom’s Carl Folta saw the story, he told Dauman, “You’re not going to believe this.”

Folta asked Sumner about it, and Sumner denied making any such call.

“Sumner, they’ve got it on tape!” Folta exclaimed. 

“Then fix it,” Sumner said.

The Electric Barbarellas debuted in MTV’s 2011 lineup and, thanks in part to the publicity surrounding Sumner, attracted nearly a million viewers. The “premiere was the #1 original cable series across all TV,” according to an email from an MTV executive to Naylor. But the show attracted some scathing reviews—a “hypercontrived, superstaged, and hair‑extensioned mess,” as a New York magazine critic put it.

Ratings rapidly fell off, and MTV canceled the show.

Redstone stayed in touch with Naylor, speaking with her by phone three to five times a week, according to Naylor. He encouraged her Hollywood aspirations and showered her with Viacom stock and other payments that totaled over $20 million, according to Herzer.

“Some who have been close to Redstone said he has long since crossed into unconscious self‑parody, making graphic sexual comments over social or business meals,” The Hollywood Reporter wrote. Said one executive: “He acts like a 15‑year‑old kid at summer camp.”

In the fall of 2010, Brandon Korff, Sumner’s twenty‑five‑year‑old grandson, enlisted Patti Stanger, the “Millionaire Matchmaker” of the Bravo reality TV hit, to find a suitable romantic match for his grandfather. Sumner’s serial dating—not to mention the accompanying bonanza of lavish gifts—was driving him crazy.

Brandon was the second of Shari Redstone’s three children from her marriage to Ira Korff, whom she’d divorced in 1992. Notwithstanding his troubled relationships with his children, Sumner doted on his grandchildren. Brandon dated a series of models and actresses in Los Angeles, some of whom in turn dated Sumner. Sumner was relentless in his insistence that Brandon socialize with him and introduce him to potential romantic companions, sometimes calling him at 3:00 or 4:00 a.m. 

Brandon brought his then‑girlfriend, a willowy brunette with long, flowing hair, to the 2009 MTV Video Music Awards in Los Angeles, where they posed for photographers with Sumner. Throughout the evening Sumner brazenly flirted with Brandon’s date, often putting his arm around her, a spectacle witnessed by senior Viacom executives sitting nearby.

A year later, Brandon invited another girlfriend and tried to enlist Malia Andelin as Sumner’s date, perhaps in hopes of fending off a similar incident. He emailed Andelin in May: “Lets us 4 go I dont want him to humiliate himself and us at MTV and if u were not here he may bring a whore.” But Andelin turned him down.

It eventually proved too much for Brandon. With the approval of other family members, he turned to Stanger.

Stanger had moved to Hollywood from Miami, where she ran a large dating service, hoping for a career as a producer. Her role model was Sherry Lansing, the former model and actress turned successful studio executive. Stanger never worked in the executive rungs like Lansing, but now she was probably much more famous, thanks to The Millionaire Matchmaker

Brash, outspoken, earthy, and funny, Stanger seemed made for reality TV. However blunt her comments, she never strayed far from a traditional narrative of love and marriage. She’d never met Sumner Redstone, but knew he was a mogul and, more to the point, a billionaire. So Stanger drove to Beverly Park to meet Sumner in person, in order to, as she put it, “read his energy.”

Her first impression was that he might have been good‑looking in his youth, but he now looked very old. She knew he was eighty‑six, but his appearance was startling nonetheless, especially his disfigured hand. She had plenty of available women interested in rich older men. Still, this might be a challenge.

Redstone seemed instantly smitten by Stanger, who checked all the boxes he told her he was looking for in both a date and a potential marriage partner—Jewish, with dark brown hair, and younger (though late forties or fifties would be fine). Sumner flirted with her, sprinkling his speech with profanities, to which she responded in kind. In the course of the interview he persuaded her to sit on his lap, which she did briefly before politely but firmly extricating herself. (Stanger had a strict rule against dating clients.

That Sumner was willing to date middle‑aged women opened up a world of possibilities. She had a long list of single, charming, and attractive older women most of her wealthy male clients wouldn’t even consider.

“Let’s do it,” she said.

Stanger explained that Sumner would be enrolled at the VIP level, which guaranteed twenty‑four‑hour, seven‑day‑a‑week access to the Millionaire Matchmaker herself. The fee was $120,000 a year, payable up front, which covered a year, although it rarely took her that long—on average, she maintained, just three dates.

One of Sumner’s first dates was with Renee Suran, an actress, a model, and the ex‑wife of the guitarist Slash. Suran was beautiful, tall, and brunette, and Sumner was crazy about her. But she didn’t reciprocate his ardor and wasn’t all that interested in his money. Sumner appeared hurt by the rejection and kept begging Stanger to arrange another date with her.

No one else seemed to measure up. Sumner often called Stanger the day after a date, screaming and berating her for an unsatisfactory match. “You don’t talk to women like that,” Stanger warned him. “I’m not fixing you up again unless you call and apologize.” Then she hung up on him. When he inevitably called back, she told him to calm down. “Are we ready to focus on love?”

Over the course of the year Sumner and Stanger became close. He seemed to like that she stood up to him and teased him, and he enjoyed her company. He told her repeatedly that she was his “dream girl.” 

At the end of his contract Sumner was the rare Stanger millionaire (or, in his case, billionaire) who hadn’t found a successful match. “What else do you have?” he kept asking, even after meeting someone he liked. Stanger offered him a 10 percent discount to renew for a second year, but he didn’t want to pay. So she encouraged him to have a second date with someone he’d earlier said he liked but had nonetheless passed over—a woman named Sydney Holland. “If what you want is me, you should go out with Sydney,” Stanger argued. “Sydney is the mini version of me.”

Holland was a personal friend of Stanger’s, not a client of the dating service. She grew up in affluent La Jolla, California, a San Diego suburb, the daughter of a dentist who died when she was twenty. She had a history of dating (and marrying) older men, and was now struggling financially. So when Stanger approached her about Sumner, she all but begged Stanger to arrange a date Stanger obliged, but issued some stern warnings: “Do not sleep with him on the first date. He’s old‑fashioned, like out of the 1940s. He could have anyone in Hollywood for sex. He’s looking for the real thing.”

Sumner responded by sending her a gift—a Judith Leiber crystal‑encrusted handbag in the shape of a panther (current versions retail for over $5,000). “I’m a panther and I’m going to pounce,” the accompanying note read.

Less than a year later, in 2011, Sumner proposed marriage, and Holland “happily accepted,” she recounted. He gave her a nine‑carat diamond ring, which she proudly showed off to Stanger. Sumner showered Holland with cash, more jewelry, art, and flowers—specifically, red roses and orchids. He bought her a house in West Hollywood, just across the Beverly Hills line, and she commuted back and forth in a new Porsche. He wrote her love notes, some on stationery from the Japanese restaurant Matsuhisa. “I will always love you. You can always depend on me. Love, Sumner,” read one.

Holland reached out to her lawyer, Andrew Katzenstein, for tax advice about the ring and other gifts. Did she have to declare the “gorgeous diamond” as income? Yes, he replied (in an email leaked to the New York Post), but added that many people “ignore” the rule. She also told Katzenstein that she was a named beneficiary in Sumner’s will to the tune of $3 million. Katzenstein estimated that, thanks to Sumner’s largesse, Holland was now worth $9 million or $10 million.

“Starting to get some comfort?” he asked. 

“20 would be best!!!” she replied. “Just saying.” 

The Porsche, house, club memberships, and cash made an impression on Tim Jensen, a Paramount employee hired in 2011 to be Sumner’s full‑time driver. When Jensen first met her, Holland had been driving a small red compact car so decrepit that its side mirror was held in place with duct tape, according to Jensen. Jensen soon realized that even though he’d been hired by Paramount/Viacom as a driver for the studio head, Holland was his de facto employer. One of his primary duties was to take checks made out to “cash” to a Bank of America branch and return with the currency—thousands of dollars at a time—which he handed to Holland. Holland, in turn, used cash to pay seven different women who visited Sumner on a regular basis. To keep track, Jensen kept a spreadsheet listing the various women and payments. In a year they totaled more than $1 million. Jensen complained to a Viacom security official in New York, in part because he didn’t feel safe carrying so much cash, and also because he didn’t consider paying these women to be within the scope of his employment. His complaint went nowhere, but Holland became “hostile,” according to Jensen, and he was fired soon after.

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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