The Disturbing Decline of Sumner Redstone (Part 2 of 3)

A lurid trial centering on the billionaire’s capacity could determine who controls CBS and Viacom.
May 5, 2016, 8:34 PM UTC
Sumner Redstone
NEW YORK - OCTOBER 1994: Sumner Redstone, the president and CEO of National Amusements, Viacom, and CBS, in October of 1994, standing in Times Square in midtown Manhattan, New York City. Redstone has an extremely prestigious resume attending Harvard and Harvard Law as well as taking his companies to the forefront of the entertainment world. One of the richest people in America, he is considered on the same playing field as Rupert Murdoch and Ted Turner. (Photo by Joe McNally/Getty Images)
Redstone in Times Square, 1994, Photograph by Joe McNally — Getty Images

With a trial about to begin, lurid and alarming details of the billionaire’s condition and the scheming around him continue to emerge. Many questions will arise in the courtroom—and control of CBS and Viacom could ultimately hang in the balance.


As Sumner Redstone reached his mid-eighties, he seemed to hanker for ever younger women, and his relations with them began to affect his image—and that of the companies he owned. Some of those companions began to wield ever more power, resembling in some ways the courtiers of a different era, as they eliminated rivals, consolidated control—and enjoyed the lucre of a billionaire’s favor.

One day during the spring of 2010, in a conference room on the 28th floor of Viacom’s (VIAB) corporate headquarters in Times Square, four senior company executives—including MTV Networks CEO Judy McGrath and programming chief Tony DiSanto—sat across from a group of five young women, costumed like off-duty strippers. They had just arrived from Los Angeles on Viacom’s corporate jet.

The executives had desperately wanted not to take this meeting. But word had come from the top—the very top—that they had no choice.

“So what do you guys do?” DiSanto gamely asked.

With that, one of the women jumped up. Throwing her hands in the air, she snapped her fingers and shimmied: “Anything you want!”

After a moment of stunned silence, DiSanto tried again: “Are you trying to form a girl band?”

“Mr. Redstone said we could have a show!” the group’s leader explained. “We want to have a show!”

A few minutes later, they burst a cappella into a song titled “Girls”:

We can dye each other’s hair, and have a pillow fight;
You can whisper in my ear, and tell me what you like…

As it turned out, “Mr. Redstone,” then 87, had taken a special liking to the leader of the group—a statuesque, 29-year-old platinum blond named Heather Naylor, who had previously worked as a production assistant at MTV’s Los Angeles office. And—as the executives soon discovered—he had indeed told them they could have their own TV show.

The executives protested vehemently to Dauman—to no avail. And so it was that, in May 2011, MTV began broadcasting The Electric Barbarellas, a reality series about the exploits of a scantily clad all-girl pop band chasing their dream of a record deal. Reviews were generally abysmal. (“Might be the phoniest reality show ever,” wrote The program would be brought back for a second season in retooled form, before MTV executives were finally allowed to put it out of its misery.

2011 MTV Movie Awards - Red Carpet The Electric Barabellas at the 2011 MTV Movie Awards.Photograph by Christopher Polk — Getty Images

Redstone’s response to a media leak about his meddling made the episode even more awkward. In July 2010, after Daily Beast reporter Peter Lauria revealed that Viacom’s “frisky” chairman had strong-armed MTV into running a show about “a sexy but talentless all-girl band,” Redstone left Lauria a lengthy voicemail demanding to know who had tipped the reporter off.

“You may be reluctant, but we have to have the name of the person who gave you that story,” said Redstone. “We’re not going to kill him. We just want to talk to him…You will be well rewarded and well-protected.” Lauria promptly wrote about the call and posted Redstone’s voicemail online. Viacom’s PR chief responded that Redstone was acting on his own, and “that there is no investigation underway at Viacom.”

By 2010, with CBS (CBS) thriving under Moonves and Viacom in Dauman’s trusted hands, Sumner Redstone had became largely irrelevant in the essential business of his companies. He remained controlling shareholder and the executive chairman of both, receiving as much as $93 million in one year (2013) for his services. (He got another $13 million from National Amusements.) He conferred periodically with his CEOs by phone, attended board meetings (often by phone), and hosted an occasional directors’ dinner at his home.

But by this point, Redstone’s whims were becoming embarrassing. His eccentric behavior needed to be managed. One research analyst wrote that he regarded Viacom’s share price as suffering from a 10% “control discount” because Redstone remained in charge, suggesting that if he were to go away, the company’s market value would jump by about $2 billion.

But Redstone wasn’t about to go away. Indeed, after surviving a bout with prostate cancer, he seemed more certain than ever that he’d never die. He credited a special diet rich in antioxidants for his “miracle recovery,” under the supervision of Dr. David Agus, a USC oncologist and bestselling author who’d become his physician. “Today, I feel better than when I was 20,” he declared. He seemed determined to prove it.

Starting in 2009, Redstone welcomed a string of decades-younger women into his orbit. The exact nature of their relationships wasn’t clear, but they appeared in public with him. Pushing 90, Redstone routinely shuffled his way into red-carpet events with his pants pulled up nearly to his chest and one or more of the glamorous consorts at his side. For his companions, even those who weren’t around long, the benefits—provided in Viacom and CBS stock, bonds, cash, jewelry, and real estate—could be transforming. The same skinflint who colored his own hair red and bought his suits off the rack at discount store Filene’s even as a billionaire lavished fortunes on his romantic interests. In the span of just three years, Redstone bestowed millions on each of five women, giving away tens of millions altogether, according to a source with access to the numbers.

Sumner Redstone, Leslie Moonves Redstone and Leslie Moonves in 2012.Photograph by Matt Sayles — Invision/AP

Rohini Singh, 30, for example, once featured in a Los Angeles magazine story on “party girls,” was spotted in public with Redstone only on a couple of occasions. After receiving millions from Redstone and, according to press accounts, a brief job in Showtime’s PR department, she bought a $2 million house in Los Angeles. Malia Andelin, a former flight attendant on CBS’s corporate jet who faced tax liens and foreclosure on a Las Vegas home she owned in 2008, began attending red-carpet events with Redstone a year later. She then bought a $2.65 million home in Newport Beach, and established her own nonprofit, Kidnected World, aimed at providing “collective, wonder-based, creative challenges” to children. Funded with $8 million in Redstone gifts, the charity placed Andelin and several relatives on its payroll; she got another $150,000 in fundraising commissions for steering $2 million of Redstone’s donations to a second non-profit.

Then there was Naylor, the former MTV assistant and leader of the Electric Barbarellas. In May 2010, after Redstone first befriended her, she signed a contract with MTV to produce her reality show. Over the next two years, Naylor bought a $1.24 million Hollywood home, and began purchasing apartment buildings as investment properties. In later litigation, a lawyer who represented Redstone placed her total gifts from the billionaire at $22 million. (Singh, Andelin, and Naylor could not be reached for comment.)

But the climactic war over Sumner Redstone’s affections—and riches—would ultimately center around two other companions: Sydney Holland and Manuela Herzer.

Redstone met Holland, then 39, in 2010. Ironically, this woman—half of the duo that would come to bedevil Shari Redstone, the mogul’s daughter—had been introduced to him through the orchestrations of Brandon Korff, Shari’s son.

Sumner and Shari Redstone at a 2012 gala.Photograph by Mark Sullivan — WireImage/Getty Images

Brandon, at 26, had moved to Los Angeles to take a job at MTV and lived for a time with “Grumpy” (as his grandchildren called Redstone). While growing close to Sumner—escorting him to events, running errands, and watching baseball and football games with him in the “fish room”—Brandon also appeared to relish LA’s fast life, driving a Bentley and posting photos on his Facebook page of himself with models and aboard private jets. He sometimes brought his female friends to Beverly Park to meet his grandfather, who greeted them perhaps a bit too eagerly.

In 2010, visitors to Beverly Park say, Brandon decided that Grumpy needed a higher class of female companionship. He retained the private services of Patti Stanger, host of Bravo’s Millionaire Matchmaker program (whose “platinum package” costs $100,000 for a year’s worth of fix-ups). Stanger tells Fortune that Brandon approached her about his grandfather, and “asked me to fix him up.” She says she introduced Redstone to several women, but he quickly zeroed in on Holland. “She was the perfect fit for him,” says Stanger. “They’re both Geminis. And she loved older men.”

Sydney’s husband, Cecil Holland, whom she married in 2000 (and divorced three years later), was 16 years older, but a handyman, not a millionaire. Holland, who earned $60,000 working at a small public relations firm, had ambitions. In 2004, she and Corinne Cliford, a longtime friend who employed Holland in a short-lived nail-polish business, placed an ad in the personals section of Los Angeles magazine. It showed both women in black camisoles, promoting The Inner Circle VIP Social Club, “a first-class dating service for exclusive gentlemen and exquisite ladies who seek to meet the love of their life!” Cliford says their intention was to use the matchmaking service merely as a platform for a TV reality show about buddy female entrepreneurs, but that the idea never got off the ground.

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A string of failed or short-lived business partnerships aimed at upscale women followed, leaving Holland with an array of debts. She was also a recovering alcoholic (she’s been sober for more than a decade, according to her lawyer). But Holland had a gift for self-promotion and networking. Says Cliford: “Sydney could sell anything to anyone.”

In April 2009, Holland’s luck started to improve: She began dating 53-year-old Bruce Parker, the wealthy former sales chief for Callaway Golf. She moved into Parker’s elegant Wilshire Boulevard condominium a month later. In court papers, Holland would claim Parker promised to marry her, and committed to providing her with $10,000 per month for personal spending as well as a new leased Mercedes, in exchange for serving as his “companion, social and business partner, and confidant.”

On the evening of Oct. 24, 2009, Parker snorted cocaine, then died after a heart attack while having sex with Holland, according to his autopsy report, which attributed his death to “cocaine toxicity.” Afterward, Holland refused to vacate Parker’s condo or turn over the Mercedes, insisting that she was entitled to $295,937 for a year of living expenses, which she claimed Parker had promised to provide if they didn’t get married. Parker’s shocked family fought her in court for a few months, before finally paying her $164,0000 to move out. (Holland’s lawyer declined to comment on the settlement.)

It was about that time—just months after her boyfriend’s tragic death—that Holland met Sumner Redstone. Says attorney Mike Gilbert, who was Bruce Parker’s best friend and represented his family trust: “She replaced a millionaire with a billionaire.”

Manuela Herzer, the antagonist in the current Redstone melodrama, also had a contentious past. Herzer says she met Redstone around 1999—before he met and married his second wife—at a Beverly Hills dinner party thrown by Bob Evans. Their subsequent liaisons in New York spurred a string of tabloid gossip mentions about the “mysterious Manuela,” who shared Redstone’s suite at the Pierre Hotel and wore a “clingy outfit” to a post-premiere party, where she spent the entire evening at Redstone’s side, “whispering in his ear.”

Then 36, Herzer was already a mother of three. Born in Argentina, she’d emigrated to the U.S. with her parents and four brothers in 1966. Herzer’s marriage, at 21, to Lebanese-born Eric Chamchoum, whose family had business interests in Nigeria, had produced two children and a nasty divorce. They separated after six years and were in court for four more. She claimed he had beaten her in front of their son, threatened to kill her, and sought “to starve us out financially,” forcing her to pawn jewelry and yank their children out of private school. He called her allegations “scurrilous,” claimed she was using their children as “hostages” to extract a fat settlement, and submitted statements describing her “violent nature” and penchant for screaming profanity. They couldn’t even agree on whether they were still married; Chamchoum claimed he’d already obtained a Nigerian divorce.

In January 1997, Herzer had a third child, from an out-of-wedlock encounter with an old boyfriend, resulting in more domestic warfare. In court filings, the child’s father said Herzer had warned his new girlfriend to “stay the fuck away from my baby” and falsely accused the woman of vandalizing Herzer’s car. He won a temporary restraining order against Herzer after he said she attacked him—screaming, scratching, and punching—in front of their daughter. The two battled over visitation.

LACMA 50th Anniversary Gala Sponsored By Christie's - Red Carpet Manuela Herzer, pictured last year.Photograph by Jonathan Leibson — Getty Images for LACMA

Herzer, who met Redstone during this period, says she refused his offer of marriage, tendered just a few months after they started dating. He went on to marry and divorce Paula Fortunato, and never resumed a romantic relationship with Herzer. But Herzer remained a figure in Redstone’s life, sharing occasional meals and sometimes called on to offer her opinion on prospective girlfriends. By 2009, Herzer and her family were living near Beverly Park, in a $3.85 million house Sumner had bought her in Beverly Hills. In 2010, she says, Redstone told her he was making provisions for her in his will.

Over the years, Viacom executives also came to know Manuela Herzer. With Redstone’s backing, she demanded VIP treatment—often for an entourage of family and friends—at red-carpet events and Hollywood parties. She raged at any perceived slight. “Do you know who I am? Sumner’s going to hear about this!” Herzer also expected personal introductions to celebrities. “How many times do I have to meet this lady’s kids?” an exasperated Justin Timberlake finally asked an MTV manager.

What became an alliance between Herzer and Holland began warily. They met at Beverly Park in late 2010, a few months before Holland moved in with Redstone, gaining official status as the elderly billionaire’s girlfriend. Yet Holland was far from the only woman in Redstone’s life. As she became more established inside his world, she began working to purge the rest. “I don’t care if you’re with a millionaire or a gas-station attendant,” says matchmaker Patti Stanger. “You want to know you’re the main girl. Sydney wanted his eyes only on her.”

But Holland wasn’t seeking to banish all women from Redstone’s life—just potential rivals for his long-term affections. She personally managed a string of others who came and went to perform for him sexually. “Sydney allowed Sumner to be with other women,” according to Cliford, who says she visited the mansion several times during this period and remained close to Holland. “But she would choose the women. And she wanted to be in control of the situation.” (Holland’s lawyer did not respond to a question on this point but asserted that Cliford was at Redstone’s mansion only once.)

Tim Jensen, a Paramount employee who worked as Redstone’s full-time driver from May 2011 to November 2012, says Holland regularly directed him to deliver cash payments around Los Angeles—typically several thousand dollars apiece—to seven different women he’d seen coming to visit Redstone at his home. Redstone typically received two or three such visits a week, says Jensen, usually for an hour or two at a time. (Jensen, who first offered his account in a first-person column published in the Hollywood Reporter last July, also spoke at length to Fortune. Holland’s lawyer says Jensen’s account is “false.”)

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Jensen, who says he kept notes and an Excel spreadsheet detailing his deliveries, places the sum of the payments he handled during 2011 at about $1 million. Jensen says he didn’t see what the women were doing with Redstone, but feels certain “they weren’t coming over to bake cookies.” He says he reported all of this to his supervisors at Paramount, but they took no action.

After finally complaining to Redstone about having to take orders from Holland, Jensen says he was fired and that Paramount offered him a $36,000 severance payment, conditioned on signing a nondisclosure agreement. He says he refused, and hopes to make more money by writing a book about what he witnessed, which he promises will include further revelations. (Upon publication of the driver’s account, a lawyer for Redstone and Holland told the Hollywood Reporter that Jensen was a “disgruntled ex-employee” who “has made claims in the past, and we don’t believe they have any merit.”)

Redstone grew devoted to Holland, who spent most of her days at his side and slept next to him at night. He called her frequently whenever she was away, and regularly sent her flowers. “Sumner cared about Sydney,” says Herzer. “She made him happy.”

But he also liked seeing other women, sometimes even calling Cliford—Holland’s close friend—to ask her to dinner and promising: “I’ll give you anything you want.” Cliford says she declined, but visited Beverly Park, where she says Redstone sang to his female visitors before being helped upstairs to bed at 9 p.m.

Because they weren’t romantic rivals, Holland and Herzer struck up a mutually beneficial arrangement. Between regular travels to New York and Paris (where she’d bought an apartment), Herzer began helping Holland tend to Redstone. Recalls Cliford: “Sydney told me straight out: She and Herzer took turns babysitting Sumner.”

In May 2011, a grateful Redstone bought Holland a house in West Hollywood, for $1.8 million. Holland began driving a new Porsche. Around this time, according to emails later leaked to the New York Post, Holland advised her probate lawyer that—counting the house, bonds, a diamond ring, and a $3 million will bequest—she’d already landed between $9 million and $10 million from Redstone.

“Starting to get some comfort?” he wrote back.

“20 would be best!!!” replied Holland. (At the time, a Holland lawyer said she doubted the emails were authentic.)

Redstone funded the launch of Holland’s film company, called Rich Hippie Productions. The announcement included a lengthy quotation from the chairman of Viacom declaring that the venture was “bound to be a tremendous success.” (It wasn’t.) In press releases, Holland began describing herself as “a nationally respected marketing executive” and “a renowned philanthropist.” She began flipping multimillion-dollar homes around Los Angeles, including one she sold to Jennifer Lawrence.

Calls to CBS helped Herzer’s teenaged actress daughter Kathrine land a featured role on Madam Secretary, a network drama. Named to the board of Al Gore’s Climate Reality Project (recipient of a $10 million pledge from Redstone), Herzer identified herself as “a philanthropic adviser to the Sumner M. Redstone Charitable Foundation” who “previously worked for CBS and Viacom.” (Both companies expressed surprise at that statement.) Herzer and Holland both established their own foundations, funded with more millions from Redstone, and made appearances at charity events. “There was a whole program to create a persona for both of them,” says one longtime observer of Redstone’s relationships. “It’s almost like reputation laundering.”

By 2013, both women were living with Redstone at Beverly Park, where they tended to his needs and managed the large household staff. Both fostered familial ties with Redstone, whose relationship with his own kin remained strained. Sumner attended the graduation of Herzer’s son from USC. In mid-2013, Holland adopted a baby girl, naming her Alexandra Red. Holland named Herzer as the child’s godmother.

On May 27, 2013, Redstone (who hated birthday parties) endured a celebration of his 90th at Beverly Park. Holland and Herzer arranged a bash befitting a mogul, with 150 guests, including Sidney Poitier, Tom Cruise, Tony Bennett, Al Gore, Michael Milken, and CBS chief Leslie Moonves. Redstone’s ex-wife Phyllis, daughter Shari, and Shari’s three adult children were there too. A 15-minute video, introduced by David Letterman, featured an array of gushing personal tributes. Viacom CEO Dauman called Redstone “my inspiration, my guiding light, my mentor, and a great friend.”

[fortune-brightcove videoid=4879640872001]

On the video, the two women sharing Redstone’s home spoke of their plans to be with him forever. “I’m so blessed to spend every day of my life with you,” said Holland, in a black sequined dress, her miniature poodle Sugar seated on her lap. “You complete me, Sumner.”

And Herzer: “They say you don’t pick your family, but they must not have had you in mind when they coined that phrase…you have honored us with your big heart. There are not enough words to express how grateful and blessed we are to be a part of your family yesterday, today, and tomorrow—and for the rest of our lives.”

In the aftermath of the 2013 celebration, the circle around Redstone started to shrink, as Holland intensified her efforts to separate Redstone from rivals for his affection. One target was Malia Andelin, a Redstone favorite, who had spent much of the 90th birthday party clutching his hand. Holland retained a private detective, who confirmed rumors that Andelin had a fiancé. She was soon squeezed out of the picture.

Heather Naylor, former leader of the Electric Barbarellas, didn’t go so easily. On June 12, Naylor stopped by the mansion to have lunch with Redstone. Holland was in San Diego that day, picking up her adopted daughter.

Court papers suggest Naylor was visiting to expose Holland. Naylor blamed her for ruining Naylor’s relationship with Redstone, leading to the cancellation of her MTV reality show. Meeting in Redstone’s “fish room,” Naylor told Redstone that Holland had been unfaithful to him and showed him embarrassing emails and photographs from Holland’s laptop. Precisely how Naylor obtained them isn’t clear. Holland claimed Naylor stole the computer, which had disappeared in 2011; Naylor denied it.

The laptop contained nude photographs of Holland and the emails to her lawyer discussing the millions she hoped to reap from Redstone. Herzer arrived to interrupt the conversation, and assured Redstone that the materials were no big deal.

This episode appears to have caused only a minor kerfuffle in Holland’s relationship with the billionaire. But Holland responded by filing a $1 million lawsuit against Naylor, setting in motion a string of unintended consequences.

"Sex And The City 2" New York Premiere - Arrivals Redstone and Malia Andelin in 2010 in New York City.Photograph by Stephen Lovekin — Getty Images

Naylor countersued, generating a spate of media coverage that offered the first peek into the strange doings inside Redstone’s mansion. Naylor accused Holland of interfering with her “business relationship” with Redstone and seeking to isolate him for “her own economic advantage” from anyone “not under Holland’s control and not a sycophant.” In court papers, she charged that Holland changed Redstone’s phone number, banned Naylor from visiting the mansion, and had a lawyer conduct lie-detector tests on the entire staff to identify anyone who might know anything about the laptop theft. Among those who were fired was Carlos Martinez, who lost his job in April 2014, after caring devotedly for Redstone for a dozen years. Charged Naylor: “Holland has effectively taken over Redstone’s life and does not allow anyone independent access to him.”

The leader of the Electric Barbarellas wasn’t the only one offering such complaints. Visitors to Beverly Park say either Holland or Herzer sat in on virtually all their conversations with Redstone. (Herzer’s attorney, Pierce O’Donnell, says Redstone “insisted” one of them be present.) Longtime friends were suddenly unable to get through to him on the phone, or hung up on. Others say they were bluntly told: “He doesn’t want to talk to you.”

Redstone’s family complained the loudest. Grandson Brandon, feeling unwelcome after many hours spent with Sumner, stopped coming to see his grandfather. Brandon’s brother, Tyler, wrote a letter to one of Redstone’s attorneys, saying “Sydney and Manuela have now blocked my siblings’ and my telephone calls to my grandfather and have effectively prevented us from speaking with him. Instead, they lie to my grandfather that we do not call him or love him.” Staff members later recounted Holland and Herzer telling them not to put through calls from Shari and her family, according to sources close to Redstone, and issuing instructions to bar Sumner’s daughter at the Beverly Park gate. (Herzer and Holland deny that.) Holland and Herzer instead cultivated a relationship with Keryn Redstone, the adult daughter of Brent Redstone, Sumner’s long-estranged son.

Herzer says she and Holland did nothing to divide Redstone from Shari and her family, but were merely carrying out Sumner’s wishes—which he’d always made perfectly clear. As their stormy history shows, Herzer contends, Sumner simply didn’t like Shari. Herzer says he regularly told his companions he hated her. “Sumner does what he wants to do,” Herzer tells Fortune. Redstone has given “many women millions of dollars over the years,” she adds. “This is his private business. Until recently, no one has taken advantage of Sumner Redstone.”

But those who were cut out believe the two women did exactly that, widening the divide between Redstone and his daughter to make the mogul ever more dependent on them. “Sumner never liked to spend time with Shari,” says one Redstone friend. “But the women did all they could to fan those flames of dislike. The more Shari went after them, the more they were able to use that against her with Sumner.”

As the billionaire grew more frail, visitors to the mansion say, they saw the women preying on his fears to manipulate him into doing what they wanted. Recalls one: “They continually told him: ‘Unless you do this, you’ll die alone.’ For an old man, that’s very scary….He was afraid to go to bed because he was so afraid of dying.” Over time, the visitor says, the women claimed “total control of everything around him. It was an amazing thing to watch. For them, it was about one thing: getting as much as they can.” Staff members recount similar stories, saying that the woman would plead, “Don’t you love us? Do you want us to be here?” (Holland’s lawyer denies the assertion; Herzer’s lawyer, O’Donnell, calls it a “blatant lie.”)

Tensions boiled over at Redstone’s 91st birthday party, in May 2014. Holland and Herzer had organized the event, held in a private room at Nobu in Malibu for about 25 guests, including various Redstones, Korffs, and Herzers. After Shari arrived to find her niece Keryn seated next to Sumner (she says Grumpy wanted her help eating), Shari angrily grabbed Keryn’s place card and moved it to another table. An ugly scene ensued, with various guests hastily relocated. The tensions carried over into the evening’s toasts, ending in screaming and tears. Recalled one guest: “It was an incredibly nasty party.”

The battle soon shifted from seating arrangements to money. In 2014, Redstone gave the two women each $45 million. He also made generous provisions for them in his will. Holland would receive his Beverly Park mansion, worth about $20 million; Herzer would get his penthouse at New York’s Carlyle Hotel, worth $3.75 million. They’d also split what was left from his personal estate after special bequests—tens of millions more for each—and become trustees of his charitable foundation.

Executive Chairman of Viacom and CBS Corporation Redstone poses after his star was unveiled on the Walk of Fame in Hollywood Viacom’s Dauman with Redstone in 2012, after his star was unveiled on the Walk of Fame.Photograph by Mario Anzuoni — Reuters

Shortly before the Nobu party, Redstone named Holland and Herzer as co-agents for his advance health care directive, making them jointly responsible for his medical decisions if he became incapacitated.

The health care proxy loomed larger during 2014, as Redstone’s health deteriorated, requiring three hospitalizations. In September, a rough bout with pneumonia required the permanent insertion of a feeding tube in Redstone’s abdomen. With Shari and his companions all on the scene, there were more angry arguments at the hospital.

When Redstone returned home to Beverly Park, he required 24-hour nursing care. He was incontinent and unable to walk without assistance. He had difficulty swallowing, requiring frequent suctioning. This left him able to speak only a few words at a time.

By that time, negotiations had resumed to buy out Shari, through a deal in which she’d trade her 20% stake in National Amusements—and her presumed right to become nonexecutive chair of Viacom and CBS—for ownership of a group of overseas theaters and two more in Massachusetts. The buyout would be worth about $1 billion to Shari. According to a term sheet introduced in the current court fight, there was a critical condition: Shari would have to agree not to bring any legal challenge to her dad’s gifts or bequests to Herzer or Holland, without even being told what they’d gotten or were due to get in his will. By year-end, Shari had rejected the deal.

Certain this meant Shari Redstone was going to come after them, the residents of Beverly Park went into war mode. In October, they’d learned that Shari had hired a retired FBI agent, who was investigating Holland and Herzer, gathering information for possible charges of elder abuse.

In fact, Fortune has learned, members of the household staff made two elder-abuse complaints to California authorities last year, months apart from each other. Investigators for the county Adult Protective Services department visited the mansion on one occasion, with police coming on the second occasion. Neither found a basis for taking action.

In January 2015, when Shari’s son Tyler wrote Redstone’s probate attorney complaining about access to Sumner, Holland rapidly dispatched a sharply worded reply—identified as coming from “Grumpy”—to another lawyer for review. In it, Sumner denied the “misapprehension” that the women were screening his calls and visitors, insisting “there has been no so-called alienation of any kind on the part of Sydney, Manuela, or anyone else.” Redstone complained that Shari had “not bothered” to call or visit despite several trips to Los Angeles.

“I love Manuela and Sydney very much,” he added. “I consider them and their children family. My sincere wish is there is no litigation—between anyone.”

That spring—at Redstone’s behest, according to Herzer—the two women retained a lawyer to protect themselves from expected attacks by his daughter. They interviewed about a dozen attorneys, including David Boies, before settling on Pierce O’Donnell.

O’Donnell, based in LA and now 69, is a hyper-aggressive trial lawyer, skilled at playing to the press to turn up the pressure on his targets. A former Supreme Court clerk once dubbed “the Perry Mason of Hollywood,” he has won landmark, high-profile cases. He also had his own brush with the law: O’Donnell served 60 days in jail and had his law license suspended after misdemeanor convictions for twice violating campaign finance laws more than a decade ago. (In a submission to the California state bar, O’Donnell blamed the violations partly on an undiagnosed bipolar disorder.) O’Donnell then resuscitated his career in impressive fashion, making a comeback at the prominent firm of Hollywood super-lawyer Bert Fields.

When Holland and Herzer met with him, O’Donnell had just won headline-grabbing victories representing Shelly Sterling against her husband Donald, owner of the Los Angeles Clippers basketball team, and V. Stiviano, whom O’Donnell attacked as “the quintessential conniving mistress taking advantage of an older, vulnerable man.” Now Redstone paid O’Donnell’s $100,000 retainer to defend his decades-younger companions against any legal onslaught from his daughter.

In April 2015, Holland and Herzer—rejecting the advice of executives at Viacom—decided to cooperate with a Vanity Fair feature focusing on their relationship with the billionaire. (It would be titled: “Who controls Sumner Redstone?”) They retained a prominent L.A. public relations firm to represent them personally, spoke at length to writer William A. Cohan (a freelancer who also contributes to Fortune), and even posed for formal portraits, meticulously made up and styled in sultry evening gowns. Certain that Shari was behind the story, they also wanted Redstone, in written responses to questions, to blast his daughter.

Leah Bishop, Redstone’s estate attorney, and Viacom executives hated the idea. Adam Streisand, a Los Angeles probate lawyer seeking to represent Herzer and Holland separately, relayed their collective advice in an email, which Herzer filed in her lawsuit: attacking Shari could backfire. “The main concern by Viacom/Leah et al. is that if Sumner shames Shari publicly that Shari will seek to establish a conservatorship over Sumner. If she does that, then his current condition will become public and Viacom will have to remove Sumner as an officer/director and stop paying him compensation…. They don’t want to poke the bear right now.” (A spokesperson for Shari asserts she never contemplated seeking a conservatorship.) In the end, Redstone’s written responses declared his love for Herzer and Holland, without saying anything about his daughter.

On May 27, 2015, Herzer and Holland again celebrated the mogul’s birthday—this time, at Vibrato Grill, a small Los Angeles restaurant. Joining the usual celebrity guests (plus Dauman, Moonves, and Paramount studio chief Brad Gray), a glassy-eyed Redstone was carried into the restaurant through a side door, behind a black curtain, and deposited into a chair. Well-wishers posed for pictures with a stony-faced Redstone, which were provided to the Hollywood Reporter. His daughter and her children weren’t invited.

A week later, Redstone signed new burial instructions, designating Herzer and Holland to preside over all arrangements. (The service was to be accompanied by Frank Sinatra’s “I Did It My Way.”) The three-page document noted that Redstone’s May 2014 will made a gift to Shari of 16 plots at the Newton, Mass., cemetery where he was to be buried next to his parents—provided that she didn’t attack his bequests. If she did, the family plots were to go to Holland and Herzer instead. Herzer’s son and two daughters were to play comparable roles in the ceremony—as pallbearer and delivering readings—as Sumner’s own five grandchildren.

Holland and Herzer’s standing as members of Redstone’s “family” seemed assured.