Inside the Raging Legal Battle over Sumner Redstone’s Final Days

With lawsuits, accusations, and sordid revelations flying, even the C.E.O.s of Redstone’s Viacom and CBS have been dragged into the mess. William D. Cohan, whose June 2015 V.F. article fueled the fire, reports on the famously cranky and willful billionaire’s last chapter.

Had everything gone according to a plan formulated last June, when the billionaire media mogul Sumner Redstone finally passes to the great beyond, not only were his two longtime female companions, Sydney Holland, 44, and Manuela Herzer, 51, to be the principal beneficiaries of his personal estate—grossing them around $75 million each, according to an inside source—but they were also to be solely responsible for his funeral arrangements.

Redstone, ever meticulous, had detailed instructions for the two women about how he wanted the funeral to go. In fact, it was a pretty comprehensive list for a man who had always insisted he would live forever.

Redstone wanted the funeral service to be private. He wanted his close friend Tony Bennett to sing. He wanted Frank Sinatra’s “My Way” to be played. He wanted to be buried in a “simple pine box,” without any personal items inside it. He wanted to be interred next to his parents, Michael and Belle (who died within three months of each other in 1987), in a traditional Jewish graveside service in the “Galilee” section of the Sharon Memorial Park, in Sharon, Massachusetts. He wanted his interment to be “an earth burial, not a mausoleum.” He wanted there to be flowers and pictures of him at the graveside. He wanted his body to be washed and “purified” by a chevra kadisha, the traditional Jewish group that cleanses a corpse prior to burial, and “thereafter, [to be] dressed in a suit.” He added, “I want no makeup, cologne, or jewelry, and no hair styling,” a strange final request from a man who for years dyed his hair a shade that can best be described as a Trumpian carrot color and whose barber, Joe, trimmed his hair every day at his mansion in the Beverly Park section of Los Angeles.

He also specified his six pallbearers: Brandon and Tyler Korff, his two grandsons; a nephew, Steven Sweetwood, who had been his longtime broker at Bear Stearns, before its 2008 demise (he is now at Stifel); Herzer’s son Bryan Chamchoum; and, finally, the two corporate C.E.O.’s who served at Redstone’s pleasure—Les Moonves, the C.E.O. of CBS, and Philippe Dauman, the C.E.O. of Viacom, the mass-media and cable giant. Redstone’s roughly 80 percent stake in the voting shares of both CBS and Viacom is the major source of his vast wealth, estimated to be around $5 billion these days. According to a 2014 document included in a recent court filing, the beneficiaries of his stakes in both companies are his first wife, Phyllis (during her lifetime), and his five grandchildren—the aforementioned Brandon, 32, and Tyler, 30, plus their sister, Kimberlee, 33, and first cousins, Keryn Redstone, 33, and Lauren Redstone, 30—through a series of carefully constructed trusts, an arrangement that is separate from his personal wealth, which was to go to Holland and Herzer.

There was more: Redstone wanted Moonves and Dauman both to deliver eulogies. He wanted Herzer’s two younger children, Christina Chamchoum, 25, and Kathrine Herzer, 19, along with his three granddaughters, to read poems or prayers. He wanted Holland and Herzer to set the guest list, but directed that it be limited to “family and close friends only.” He did not want his two offspring, Shari and Brent, involved in any of the decision-making about the funeral arrangements, evidently the legacy of the often tempestuous relationship he has had with them. “I previously directed that certain family members not be allowed to attend,” he wrote in a June 2015 directive, likely referring to his estranged son, Brent. “That decision should be made by Sydney and Manuela, at their discretion. I have no objection to my family members attending so long as they do not interfere with any aspect of these instructions.” The two women were also put in charge of the reception after the funeral. Redstone wanted it to be “festive, not solemn.” If anyone in the family “was unwilling to participate with other people” he had named, they were to be “excused” from the ceremonies.

He seemed particularly concerned that his only daughter, Shari, 61, would, after his death, contest his decision to give the bulk of his personal fortune to Holland and Herzer. He has long had a complicated and rocky relationship with Shari. During some periods over the years, they have been estranged. For years, Sumner had tried to get her to sell him her 20 percent stake in National Amusements, Inc., the family’s privately held movie-theater business, which also serves as the de facto holding company for the ownership of CBS and Viacom.

He wanted her gone from the business. “Sumner and Shari are not getting along,” according to an informational “Term Sheet” about a proposed buyout deal, drafted in late 2014. “Shari wants to continue to expand the foreign theatre business, while Sumner has no interest in doing so.” A possible deal was negotiated: in exchange for her 20 percent stake in N.A.I., Shari would get the company’s foreign movie-theater operations, plus the two movie theaters near Boston that she “helped develop.” The deal for her 20 percent stake was estimated to be worth $1 billion.

Among the conditions outlined in the Term Sheet, Sumner also wanted Shari to agree not to question the gifts that Holland and Herzer had already received from him—which, according to people close to Redstone, may have amounted to about $70 million each. In 2014, Redstone had sold around $300 million in Viacom and CBS stock options and made “substantial gifts” to the two women “to ensure that we would be cared for during the rest of our lives,” according to Herzer. “He did not want us to ever have to worry about our financial security, especially after his demise.”

Redstone knew that Shari had hired a private detective, Jim Elroy, to investigate the two women. (Reached by phone, Elroy declined to comment about his work for Shari Redstone.) “It’s upsetting that this is happening,” wrote Leah Bishop, Redstone’s personal estate lawyer at Loeb & Loeb, in a November 2014 e-mail to Holland and Herzer, “but Sumner cannot stop Shari from doing this.” So the deal to buy Shari’s stake in N.A.I. tried to address this concern as well. Contractually, there was to be no litigation between Shari and Sydney and Manuela. Holland and Herzer would get to “keep all of the gifts they have received”—whose value would not be disclosed to Shari—and Shari had to agree “not to bring any action for repayment.” Furthermore, N.A.I. would cover the huge tax bill—estimated at around $100 million—for Sumner’s lavish gifts, as well as the taxes on whatever he would leave Holland and Herzer upon his death.

Redstone also acknowledged his ongoing worries about his wishes for Herzer and Holland in a January 2015 e-mail to Shari’s three children. “I love Manuela and Sydney very much,” he wrote (or more likely dictated). “I consider them and their children family. My sincere wish is that there is no litigation—between anyone. I ask you to honor this wish.” He signed off, “Love, Grumpy,” his tongue-in-cheek nickname for himself with them. His concerns were reinforced in the June 2015 funeral instructions, in which Redstone specified that if Shari disputed his estate plan the 16 cemetery plots in his name at the Sharon Memorial Park would no longer be hers, as he had instructed in his July 2014 will, but instead would go to Holland and Herzer.

This last request must have been particularly galling to Shari, since it would have meant that her father’s two girlfriends and their families could be next to him for eternity, rather than his own flesh and blood. “Sumner wanted to make sure that the world knew that [Shari] was not in his life, by his choice, and that he wanted [Holland and Herzer] to have everything if she wasn’t going to comply with his wishes,” says a onetime close friend of Redstone’s. “That’s how adamant he was about protecting [the two women]. I mean, if that’s not black-and-white, I don’t know what is.”

But—surprise!—things will not go according to this plan, not even close. Shari rejected the buyout deal—“because she’s so greedy, right?”—said the former friend. (Shari’s spokesperson, Nancy Sterling, wrote in a statement, “Shari initiated discussions to sell her interest in National Amusements Inc. back to the company. By the end of 2014, no deal had been reached and Shari terminated the discussions.”) And both Holland and Herzer are gone, not only from Redstone’s side but also from his personal will. They are no longer its beneficiaries, and whether they will get to keep the estimated $70 million worth of cash and gifts Sumner already bestowed on each of them remains to be seen. They are no longer in charge of his funeral arrangements or named in his advance health-care directive, which gave them power of attorney for making his medical decisions in the event he was no longer able to decide for himself. They will no longer run his charitable foundation.

Through a combination of their own mistakes and the machinations of others, the entire calculus of Redstone’s endgame has been upended and thrown into turmoil. A legal battle is raging, churning up personal recriminations, power plays involving billions of dollars, and a slew of extraordinary and embarrassing revelations that, by all rights, should never have been made public. Even Dauman and Moonves have been dragged into the mess.

Shari and her family are back at her father’s side. (His house in Los Angeles is a quick hop by private jet from her $10 million apartment at the Pierre hotel, in New York City, or her house in the Boston suburb of Westwood.) She said in a recent affidavit that she has “patched up” her long-running disagreements with her father and that “family has always been the most important thing to me.” Since mid-November, she wrote, “I have traveled from the east coast to Los Angeles to visit with my father in his home on 39 days. When I cannot be with my father in his home, my father and I ‘face-time’ by telephone, sometimes more than once a day.”

Shari seems firmly in control of Redstone’s day-to-day care—as of this writing he seems to be hanging on by a thread—and seems likely to have the necessary votes and authority to take control of the trusts that will decide the fates of Viacom and CBS when he dies. The money in his personal estate that was once earmarked for Holland and Herzer is to be donated to charities, thus saving Shari and her family millions in taxes that N.A.I. would have paid. “It’s a coup,” says the onetime friend of Redstone’s. “It’s a fucking coup.”

Girls of Sumner

It’s also an extraordinary turn of events for Redstone, a virtually self-made man who once upon a time, in a 1979 Boston hotel fire, clung to the window ledge of the burning building for dear life while flames lapped his body and melted his hand into a claw, until he could be rescued by a fireman on a ladder.

Less than a year ago Herzer and Holland were so confident of being Redstone’s principal gatekeepers and beneficiaries that they decided to reveal their roles, in the June 2015 issue of Vanity Fair (in “Endless Sumner,” by William D. Cohan). They posed for pictures, looking seductive in evening dresses, Holland in Pasadena and Herzer at Bemelmans Bar, in New York’s Carlyle hotel, downstairs from the multi-million-dollar apartment Redstone had bought for her. They were proud to share how important they were to Redstone. In the course of reporting the story, I heard again and again how closely they kept track of who saw him and who didn’t, including his daughter and his grandchildren, as well as both Dauman and Moonves.

Shari Redstone felt shut out, and she wasn’t happy about it. “It seemed to me,” she wrote in a February 2016 affidavit, “that my family was effectively prevented from having meaningful access to my father” by Herzer and Holland, who “made it clear that we were not welcome in my father’s home. On those occasions when visits occurred, Ms. Herzer and/or Ms. Holland appeared to try to monitor communications with my father, with one of them usually sitting close as we tried to have private, family conversations with my father, and insisting on remaining in the room with us.”

In a court filing, Herzer says this was not true. She claims that neither she nor Holland prevented Shari or her family from seeing Redstone and that he made all decisions about whom he would see, which generally did not include Shari. According to Herzer’s filing, Redstone told her, “Shari is all about money…. A billion dollars is not enough for her,” referring to the N.A.I. deal that fell apart. “Sumner and I treated each other like family,” Herzer says. “Anyone who knows Sumner knows how he feels about Shari. He instructed everyone around him to just ‘ignore her.’ ”

Redstone himself backed up Herzer’s view of access to him. In the January 2015 e-mail to Shari’s children, he wrote, “I need to clear up another misapprehension—neither Sydney nor Manuela controls the phones in my home.” He wrote that he had a “log of every incoming phone call” to prove his point. “There has been no so-called alienation of any kind on the part of Sydney, Manuela, or anyone else, and please do not insult me by suggesting otherwise. From what I’ve heard my daughter Shari has been to Los Angeles several times and has not bothered to call or visit me.”

Manuela Herzer is a Jewish Argentinean beauty whose grandparents owned “a lot” of Buenos Aires real estate, she told me. When she was two, the family moved to Miami. She studied in Paris. She speaks English, French, and Spanish fluently. After divorcing Eric Chamchoum, the scion of a wealthy Lebanese family, and having a third child out of wedlock—Kathrine Herzer, who plays Alison McCord on the hit CBS show Madam Secretary—she was introduced to Redstone in 1999 by his longtime friend Robert Evans, the Hollywood producer. She and Sumner fell in love and dated for about two years. In 2000, she told me, he proposed marriage, but she declined, saying she did not want to re-marry. They remained friends, however, and Redstone often asked Herzer to vet the young women in whom he had taken an interest. In 2009, Redstone “surprised” Herzer and her children by buying her a home not far from his Beverly Park mansion. In 2013, she said, he asked her to take up residence at Beverly Park, which she did off and on for the next two years. A 2015 version of his will gave her $50 million in cash, plus the Beverly Park mansion, worth around $20 million.

Holland became Redstone’s live-in girlfriend in 2011, a year or so after they had been introduced by Patti Stanger, the host of a Bravo reality show called The Millionaire Matchmaker. Born Sydney Stanger (no relation to Patti), Holland came from a well-to-do family in La Jolla, California. Her father, a cosmetic dentist, pioneered the use of veneer to improve the look of teeth. Her mother, a social worker, specialized in interventions in Los Angeles. Holland has a complicated personal backstory, including a few failed businesses, one of which was a Los Angeles matchmaking service. In 2009 her 53-year-old fiancé died suddenly from “cocaine toxicity” while Holland was in his Wilshire Boulevard apartment.

At the time that Stanger introduced Holland to Redstone, Holland was in debt and down on her luck. Her relationship with Redstone changed all that. Her debts disappeared. She started Rich Hippie Productions, a currently inactive Hollywood production company, and a personal charitable foundation. According to people who shopped and traveled with her, she had nearly unlimited access to Redstone’s money, which she used to charter private jets and buy expensive clothes. She also began to purchase, renovate, and sell homes in Los Angeles. Redstone was supposedly fine with that arrangement. “He didn’t want [Holland and Herzer] to pay for a fucking thing, not one thing,” says the onetime close friend. “He would get mad, on the contrary. He’d be like, ‘No, I’m paying for everything.’ Don’t forget, Sumner’s not about money at all…. He’s old-school—he takes care of whoever he wants to take care of.”

George Pilgrim, who dated Sumner’s onetime girlfriend Sydney Holland.PHOTOGRAPH BY JOE PUGLIESE.
George Pilgrim, who dated Sumner’s onetime girlfriend Sydney Holland.PHOTOGRAPH BY JOE PUGLIESE.

But going public turned out to be a tactical mistake for the two women, setting off a chain of events that ended with both of them banished from Redstone’s life. Enter George Pilgrim, a 49-year-old former actor and ex-con living in Sedona, Arizona. (Pilgrim had served 27 months in prison after being convicted of tax evasion and wire and mail fraud.) He read the 2015 Vanity Fair article closely, and he did not like what he read. According to Pilgrim, he had been dating Holland since the previous summer and had fallen in love with her. He says Holland had heard about him when he was living in Los Angeles—“I had a colorful life living in the Hollywood Hills on Appian Way,” he says—and she wanted to option Citizen Pilgrim, his unpublished autobiography, for Rich Hippie. He says initially he had no idea that Holland had anything to do with Sumner Redstone, let alone that she was his live-in girlfriend, but she told him that Redstone owned Simon & Schuster, the book publisher, and Paramount Pictures, and both companies were interested in Pilgrim’s story.

By early 2015, Pilgrim was living in a $3.5 million house she had bought in Sedona. He believed they would soon be married. She regularly sent him videos of herself in the Beverly Park mansion, sharing with him her plans for the day and showing off her outfits. “I have dozens [of videos],” he says. The course of their relationship is documented in text messages that Pilgrim has shared with Vanity Fair. (Through lawyers, Holland has declined to answer specific questions.)

In late 2014, Pilgrim says, he proposed marriage.

“Is that yes?” Pilgrim texted Holland.

“Yes, yes,” Holland replied.

“Omg. I’m so happy,” Pilgrim replied.

“Me too,” Holland texted, along with more than a dozen heart emojis.

Assuming they would be married, Pilgrim says, he planned to adopt Holland’s young daughter, Alexandra Red, who was borne by a surrogate and had been raised in Redstone’s home. (Last year, Redstone told me by e-mail, “I love Sydney and Alexandra.”) Pilgrim and Holland had started their own process of in-vitro fertilization, he says. On October 28, 2014, he donated his sperm. “I gave you my blood today,” he texted her. “My sperm.”

“I know. Thanks,” she replied. “I give you my heart and soul.”

On a regular basis, Pilgrim says, Holland would fly to Sedona by private jet, spend the day with him, and then fly back to spend the night at Beverly Park, presumably without Redstone’s having a clue where she had been or what she had been doing. Pilgrim was concerned that Holland was living with Redstone, but, he says, she assured him that her relationship with Redstone was not based on genuine emotion; it was a financial investment, designed solely for cashing in on Redstone’s wealth. The texts between her and Pilgrim bear witness to that view. In one, she wrote Pilgrim that Redstone “is old and crying all the time” and that during a visit Shari and her family “won’t be able to do much[.] I will be there the whole time[,] so will pitbull [her nickname for Herzer].”

“I definitely wouldn’t leave [Sumner] alone with any of [Sumner’s family] now!!!” Pilgrim replied.

“No way!!” Holland wrote.

“Fuck them,” Pilgrim replied.

“Exactly,” Holland texted.

Pilgrim seemed to believe that Holland was just waiting around for Redstone to die and for her to collect her millions so that they could then live happily ever after. “We need to be a family healthy working and having fun,” he texted her. “This old man is draining u!!! He better come through.”

“I agree,” she replied.

(In fairness to Holland, Herzer intimated to me last spring that Holland deserved the big payday she was expecting: “I mean, five years of your life with a man every single day like that. I have to tell you, would she be there if he wasn’t doing something for her? Probably not. But does she love him? Absolutely…. She has his best interests at heart. For her it’s a job almost, it’s a job.”)

Pilgrim’s Pride

Pilgrim says he couldn’t believe his eyes when he read about Holland and Redstone in Vanity Fair, especially the passages about how much Holland loved Redstone, how beautiful his hair was, and how he had such soft skin. “I blew up and lost my temper,” he recalls, “and I think I lost my shit—excuse my French. I did, and I confronted her about it and said, ‘What the fuck is this?’ I said, ‘I don’t understand, Sydney. I’m flying back and forth on private jets. You’re flying out here, buying me houses—you’re giving me the world. We’re supposed to have a fucking life, and all Sedona, Arizona, knows about us.’ I said, ‘My family and everybody wants to know what’s going on.’ ”

Pilgrim says things went downhill quickly. “It hurt,” he continues. “It hurt me very, very bad. I didn’t understand. And I’m just like looking at myself in the mirror like, ‘Why, God? Didn’t I pay my dues going to prison? Haven’t I done enough?’ I mean, I lost everything…. I was trying to really, you know, change my life, man, you know?”

In June 2015, Pilgrim says, Holland insisted that he enter the Arbor, a rehab center outside Austin, Texas, for a 30-day program because she claimed he had a drinking problem. He says she promised him “a huge party” when he got back to Sedona, but instead she had his possessions removed from the Sedona house and the locks and security codes changed. When Pilgrim got word of what was happening, he says, he left the rehab clinic with no money and no ID and persuaded a cabdriver to drive him 18 hours back to Sedona.

Pilgrim refused to go quietly. He hired Bryan Freedman, a tough Los Angeles litigator, to threaten to file suit against Holland unless she entered into settlement negotiations with him. Discussions were under way by the end of July. He initially wanted $25 million but soon proposed $4 million in cash up front plus another $6 million spread out over the next 25 years, plus another $7 million when Redstone died. After much back and forth Holland made a final counter-offer: $2 million from the sale of the Sedona house, $2 million spread out over 100 months, and 5 percent of what Holland received from Redstone’s estate, subject to a floor of $1.5 million and a cap of $4 million. Holland also wanted a restraining order and suggested a clause that would keep Pilgrim 100 miles away from her, meaning he could no longer go to Los Angeles, where his two daughters from a previous marriage lived. In the end, this proved to be a deal breaker. He walked away from a settlement worth $6 to $8 million. “I didn’t want her money,” he says. “I wasn’t going to let her treat me like I’m some fucking Gucci bag.”

Without a deal, Pilgrim no longer felt the need to be discreet about his relationship with Holland, and word of it quickly got to Redstone, who was enraged. On August 30 he kicked her out of the Beverly Park mansion and within days removed her from his will and as one of the power-of-attorney designees on his health-care directive, leaving Herzer alone in that role. Holland has said nothing publicly about the end of her relationship with Redstone. Some think that he gave her a fresh $35 million for her to fade away quietly or made a $35 million donation in her name to a charity she supported. But an attorney for Holland denies that she received a parting gift of any sort from Redstone. “It’s absolutely false,” he says. A source close to Holland says that she still loves Redstone and that it is “extremely painful” for her to watch from afar what is happening to him. Meanwhile, a source close to Redstone says that Redstone’s credit-card bills are “10 percent” of what they were when Holland was in his life.

According to the onetime close friend, when Redstone re-did his will, in September, to eliminate Holland, he wanted to give the bulk of his personal estate to Herzer, but after discussions with Leah Bishop, his estate-planning lawyer, he changed his mind. Instead he bequeathed to Herzer $50 million in cash and the Beverly Park mansion. Much of the rest of the estate was designated for charity, with small bequests for people such as his longtime secretary. Brent’s daughter Keryn Redstone was slated to get $6 million.

With Holland gone, Herzer took control of Redstone’s life, and on September 3 he signed a new health-care directive naming her as his health-care agent. At that time, Herzer said in her petition to the court, Leah Bishop asked Redstone whether he wanted Herzer to serve in this capacity alone or with Philippe Dauman. Redstone replied that he wanted Herzer to have sole responsibility. Dauman was named the “first alternate” agent.

Herzer moved back into the Beverly Park mansion on nearly a full-time basis, even though her own house was nearby. She was now the only person in charge of Redstone’s health care, she wrote in another declaration to the court. There had already been serious scares. In 2014, Redstone had been hospitalized on three separate occasions, twice for aspiration pneumonia, a potentially severe form, according to Herzer’s court filings. He lost the ability to “eat, drink, and vocalize clearly” after his third hospitalization, she added. His doctors said he would need a feeding tube in order to survive. Herzer claimed Shari and her son Tyler Korff—two of the seven trustees of the family trust—opposed the feeding tube on religious grounds. (“Neither Shari, Tyler, nor anyone in her family, opposed the insertion of a feeding tube,” counters Shari Redstone’s spokesperson.)

Herzer and Holland had the feeding tube installed, “to prolong his life,” Herzer claimed, though the quality of his life would be forever changed. “Although therapy helps, Sumner’s doctors believe that he will never be able to eat, drink, or speak intelligibly again,” she wrote. He can “barely vocalize,” she continued, and gets “emotionally distraught” because he can’t eat or drink. The picture painted in Herzer’s filing was bleak: Redstone was crying a lot for apparently no reason; he was basically unable to leave his mansion; he required a catheter to urinate and sleeping pills to sleep; he was unable to walk or stand by himself and had to be carried from the bedroom to the living room to the bathroom; he required around-the-clock nursing care. There was, in effect, “an intensive care unit” in his home, Herzer concluded.

Sumner’s longtime friend and caretaker Manuela Herzer.PHOTOGRAPH BY JOE PUGLIESE.
Sumner’s longtime friend and caretaker Manuela Herzer.PHOTOGRAPH BY JOE PUGLIESE.

Gone Girls

With Holland’s banishment in the summer of 2015, Redstone’s health again deteriorated rapidly, according to Herzer. “The sudden loss of her regular companionship—and shock at her betrayal—se[n]t Sumner into a visibly downward spiral both physically and mentally,” she wrote in her filings.

On September 9, soon after Herzer’s return full-time to Redstone’s side, the New York Post reported that she could be the next to go. Concerned, she contacted David Andelman, Redstone’s longtime personal lawyer (and a member of the CBS board of directors), to inquire whether it was true. Andelman told her by voice mail not to worry. “It’s not a big deal,” he said, according to Herzer. “We know Sumner is not going to do anything with you, but you know you are in great shape there…. Let’s just let it go.”

Suddenly, Herzer had to confront an unexpected crisis: the Beverly Park mansion was found to be infested with termites. The exterminators wanted to fumigate the place, but Herzer did not want Redstone exposed to the chemicals. She decided to move him to a Malibu oceanfront home that he had previously arranged to rent for six months from its owner, billionaire Larry Ellison. (“Sumner loves the ocean in the summer,” Herzer explains.) In the court papers, there is a picture of Redstone, sitting on a couch in Ellison’s house, his hair completely white, with a vacant expression on his face.

In Malibu, Herzer claims, Redstone became obsessive about wanting to have sex. After his wife Phyllis initiated divorce proceedings, in 1999, he had gone on a dating spree, meeting with a slew of beautiful women, often with Herzer’s help. According to the onetime close friend, one of those women remained on retainer with Redstone, getting $5,000 a month at the gate to Beverly Park whether she saw him or not. In Malibu, Redstone relentlessly called out for her, demanding that she come over. But she didn’t answer her phone. Back at Beverly Park, post-fumigation, Redstone continued to pine for her. She showed up, but “he can’t have sex, so it’s all in his head, right?” says the onetime friend. “How can a guy with a feeding tube who can’t move have sex? There’s no sex.”

She was not the only woman who continued to come to the mansion, however. In early September, Herzer got back in touch with Heidi MacKinney, another Redstone favorite from the old days. “Sumner wanted to see me,” she wrote in a court filing. But he was not the same. “Mentally, Sumner was not present,” she wrote. “He did not seem able to communicate with me, was frail looking, and was not fully aware of his surroundings or what was happening around him.” She met with him five times after he kicked Holland out. On her fourth visit, on October 3, he was “completely non-responsive and vacant,” she wrote. She offered to have sex with him. He did not respond. “It was as if he did not understand what was happening.” She resolved to stop coming to see him.

A week later, though, according to MacKinney’s filing, one of Redstone’s male nurses called MacKinney and said Redstone wanted to see her again. She returned for her final visit to Beverly Park. “This time he appeared even more disoriented, distant, and non-communicative,” she wrote. She spent 20 minutes with him. “It was clear to me that he was not aware of my presence, much less able to communicate with me.” Nevertheless, she continued in her filing, the male nurse—identified in Herzer’s filings as Jeremy Jagiello—remained in the room with her and Redstone, “directing me and telling me what sex acts I should perform.” Jagiello would “sometimes tell Sumner that he had ejaculated, when in fact Sumner had not,” she concluded. “Sumner appeared to believe him, not aware of the truth.” (Attempts to reach Jagiello were not successful.)

Then there is supposedly a sex tape, made by one of Sumner’s “handlers” inside Beverly Park. According to people who have heard about it, the tape shows a “butt naked” Redstone watching two women kissing. “He’s just sitting there, kind of like comatose,” says one of the people who heard about its contents. Then Redstone heaves himself over the armrest of the chair, and the two women direct their attentions toward him. The other person who heard about the contents of the tape said just visualizing the scene “ruined my sex life for a couple of weeks.” (Redstone declined to comment.)

By fall the deterioration in Redstone’s health had become severe, Herzer wrote in her court filings. He no longer understood the significance of recommendations made to him, was no longer able to follow the plots of movies and TV shows, lost interest in current events and business news, and lost the “ability to modulate his emotions, often experiencing spontaneous crying spells.” He was no longer interested even in the stock prices of CBS and Viacom, or in his tropical fish, a longtime passion. Herzer’s filings relate that Redstone’s dermatologist described him as “out of it.”

According to Herzer’s filings, one of the recommendations Sumner received—and ignored—was to conserve his energy by reducing his sexual activity, such as it was, to once a week. If he had more energy, he was allegedly told, he might be able to pass his swallowing test, which would allow the feeding tube to be removed from his throat, enabling him to eat steak. “Sumner is obsessed with eating steak,” Herzer wrote, “and would attempt to eat one if it were placed in front of him, not seeming to recall or understand why he cannot do so.”

On October 7, according to Herzer’s filings, Leonard Goldberg, a longtime television producer and CBS board member, visited Redstone with his young granddaughter, who wanted to see his tropical-fish tank. She said hello to Redstone, but he did not acknowledge her. “Sumner appeared especially vacant and absent that day,” Herzer claimed. (Goldberg did not respond to a request for comment.) That same day, Redstone became “irate” about his granddaughter Keryn’s use of his credit card to pay for her move to Los Angeles to stay with him, Herzer continued, explaining that he had given Keryn permission to use the card days before but could no longer remember doing so.

Just the day before, even though the Viacom stock had fallen by around one-third since the start of 2015, the press had received a statement expressing Redstone’s support for Philippe Dauman. “Philippe is my long-time friend and partner,” the statement began. “He continues to have my unequivocal support and trust, which he has earned over our many years together…. We are both long-term thinkers and I am more confident than ever that he is on the right track.”

According to Herzer’s filings, Redstone did not write or dictate the statement. “Sumner did not say or articulate the flattering words,” she claimed. On October 8, Dauman said, he met with Redstone for more than an hour and found him “engaged and attentive.” But Herzer, who was present during the visit, said that Redstone was “gazing somewhat vacantly” at the television during the meeting, which was “20–30 minutes at the most,” and that “there was no two-way conversation or discussion between Mr. Dauman and Sumner…. It was a monologue by Mr. Dauman.” (An attorney for Dauman said that his client would not comment on anything related to this case, except to say that “Herzer and her lawyers have shown themselves fully capable of inaccurate and self serving public statements.”)

On October 11, Redstone invited his friends the Kopelsons—Arnold Kopelson, a veteran movie producer of such films as Platoon, The Fugitive, and Joe Somebody, is also on the CBS board—to Beverly Park for his regular Sunday movie screening. Herzer was there, along with her brother Carlos. On tap was Steve Jobs, the film about the late Apple co-founder. “In the past Sumner greatly enjoyed hosting his friends for movie day,” Carlos Herzer explained in a declaration in support of his sister’s case. “Sumner … appeared out of touch, remote and non-responsive to the people around him. While in the past I had seen him disinterested and even fall asleep when a movie did not keep his interest, this time was different. He seemed very weak and emotional, and he did not seem well.” Before the movie started, Manuela Herzer wrote in a filing, she saw that Redstone was having trouble breathing because his throat was blocked. She ordered everyone out of the room and brought the medical staff in to suction out his throat and clear the obstruction.

The Kopelsons returned and the movie played, but Redstone was still not well and fell asleep. (Kopelson did not respond to a request for comment.) The nursing staff removed him from the home theater. Later, Herzer says, she checked on Redstone and found him in a very deep sleep, in the middle of watching a baseball playoff game. It was only 6:30 P.M. She woke him and asked him if he wanted to go to bed. He shook his head no. She instructed the nurse on duty to put him to bed if he fell asleep again. “I was troubled by Sumner’s unusual behavior that day,” she wrote.

Sotto Voce

There were other signs that Herzer found troubling. Jagiello, Redstone’s principal nurse, had allegedly started translating his grunts into definitive statements of his desires. Inside the house, she says, the staff started referring to Jagiello as “the Sumner Whisperer.” Herzer says she did not at first realize what Jagiello was doing. She thought he was being helpful: significantly increasing his work hours, staying late, and caring for Sumner. More and more, though, she felt that Jagiello was acting as Redstone’s interpreter. If this had started out as innocuous, Herzer claimed, increasingly it was not.

On October 12, according to Herzer’s court filings, all hell broke loose at Beverly Park. At eight A.M., she told Jagiello that Redstone’s doctor should be summoned to see why he was falling into such deep, trance-like sleep. She then left Beverly Park to do some errands.

When she got back to the house, later that morning, Herzer says, security wouldn’t let her through the front gate. She went to the back gate and used her security code to get in, only to be confronted by Redstone’s driver, Isileli Tuanaki. “Mr. Redstone doesn’t want you here,” he told her, according to her filings. Herzer ignored Tuanaki and proceeded to the sitting room, where she saw Redstone, Bishop, and Jagiello. “A frenzy ensued,” she wrote, claiming that Bishop told her, in a loud voice, “You can’t be here!” Bishop was holding her cell phone. They were talking with David Andelman, wrote Herzer, remembering the conversation: Bishop told Andelman, “Manuela is here, but is not supposed to be here, I don’t know how she came in.” Herzer started shaking. She asked Redstone if he was O.K. and if he wanted her to leave. “Sumner did not respond,” she claimed. “I asked again and Sumner made a grunting noise and began crying uncontrollably.” She remembered asking Jagiello what Redstone had said and Jagiello replying that Sumner wanted her to leave. But Herzer believed that Sumner had made no intelligible comment. Herzer asked Bishop what to do. She replied that Redstone wanted to speak with her and Andelman alone and that she should leave. She could come back later, when their conversation was over. (Andelman declined to comment; Tuanaki could not be reached for comment; and Bishop did not respond to repeated requests to comment for this article. )

This was unusual, Herzer thought, but she complied. She went up to her room. Tuanaki came by and told her to leave the house. He said they would call to tell her when she could come back. She was incredulous. She went to her daughter’s house and tried to calm down. She called Bishop’s cell phone, but Bishop did not pick up. Before long, Tuanaki called her and told her she could come to the house to get her things. When she arrived, an armed guard followed her to her room. She told him to get away from her and said that she wanted to see Redstone. He also said Redstone did not want to see her. She tried calling Bishop again but got no answer. The security guard told her that if she did not leave he would have her thrown out of the house.

She left Beverly Park because they were threatening to call the police. “I’ve never been allowed back,” she says. “They have not let me see him since that day…. I’d love to see him. It’s not fair.” She eventually spoke to Bishop, who declined to tell her what was going on. “She would only tell me that I had ‘lied’ to Sumner,” Herzer later wrote in a court filing. She spoke to Dauman, the filing continued, and he explained that her supposed lie involved giving Keryn Redstone permission to use Redstone’s credit card to pay for her move to Los Angeles. “I did not lie,” she maintained. “Sumner had simply forgotten what he had said.”

On October 16, Redstone signed a new directive, replacing Herzer as the person named to take charge of his health care, and changed his will. The $70 million she was to receive was designated to go instead to his charitable trust, which she was removed from running. In a court filing, Herzer claimed that Shari was motivated to make this change to her father’s will in order to get more money for herself, since N.A.I., of which she owns 20 percent, would be obligated to pay any debts or taxes that Redstone owed at his death. If the $70 million went to charity, there would be no gift tax on it. (“All of these allegations are false,” says Shari Redstone’s spokesperson.)

In his new health-care directive, Redstone named Dauman as his agent. He was to share that responsibility with Thomas Dooley, Viacom’s chief operating officer. This was an odd development, since both Dauman and Dooley have full-time jobs at Viacom, in New York. In a separate letter, Redstone instructed Dauman and Dooley to consult with Shari about his health care, if necessary. Redstone’s signature on the new health-care directive, notarized by Leah Bishop, is a long sweeping downward arc that trails off the bottom of the page. Herzer brought in Jim Blanco, a handwriting expert, to examine Redstone’s signature on a November 19 document that gave Herzer four hours to remove her belongings from Beverly Park. Blanco found it to be “a poor attempt at a forgery.”

After he had been appointed to replace Herzer as Redstone’s health-care proxy, Dauman called her. As she remembers the conversation, he said, “Manuela, now you have so much money. You have a beautiful family. You’re a nice person. You have everything. If you ever need anything, you can always call me. I’m going to take care of Sumner.” Herzer was incredulous. “Philippe, how are you going to take care of Sumner?” she asked him. “You live in New York!” He replied, “Manuela, please listen to me. I’m going to hire the best people. You know there’s nothing more you can do for him. These are his words. He loves you. He loves your family. Don’t worry, I’ve got your back.”

On November 3, Dauman wrote in an affidavit, he again met with Redstone for 90 minutes at his house. “I found him to be engaged and attentive,” he added. He said that Redstone told him that Herzer was threatening to litigate “and that all she wants is his money.” He said they spoke about “business matters,” an upcoming Viacom board meeting, an investor conference he was attending the next day, and “personal matters.” According to Dauman, they watched a basketball game together and spoke about a movie Redstone had recently seen. He explained that he believed Redstone’s “mental acuity” had not changed since he had seen him on October 8. “On both occasions,” Dauman wrote, “[Sumner] was engaged, attentive, and opinionated as ever.” He asserted, “I care deeply for Sumner and will do whatever is necessary to ensure that he continues to receive superior care.”

On November 23, Herzer removed her clothes and personal effects from Beverly Park: “When I went to the house to retrieve my things, they divided the house with the biggest, longest black curtain I have ever seen,” she recalls. “They placed security guards all over the house and hid the staff. It was eerie! It was heartbreaking for me to think he was behind the curtain, not knowing I was there and wanting to see him. I have requested many times to see him. They will not let me see him. He is a prisoner in his own home.” Two days later she filed suit in California state superior court seeking to reinstate the earlier health-care directive that had made her Redstone’s sole health-care agent. In addition, she wanted to take a slew of depositions, have Redstone examined by her chosen physician, and get a ruling that he was not “competent” in that crucial time period when he threw Herzer out of his house and cut her out of his will. In additional filings, she argued that others—mainly Shari Redstone—had manipulated him to get her out of the house and get his money and power. To this charge, Shari’s spokesperson issued a response saying, “Ms. Herzer’s attack on the Redstone family reached a new low with her unfounded claim to the court that Shari’s devotion to her father is motivated by money or power, and not love. The family has no financial interest in the case and always understood and supported Sumner’s plan to honor his legacy by leaving his estate largely to charity. Shari and her family are well provided for by the multi-billion-dollar company National Amusements, Inc.” In addition, Redstone’s attorney, Gabrielle Vidal at Loeb & Loeb, responded, “As we have said before, Ms. Herzer’s action is meritless, riddled with lies, and a despicable invasion of his privacy. We are confident that when the Court has evaluated the evidence it will determine that Mr. Redstone had capacity to change his health care directive and that Ms. Herzer should have no role in his life whatsoever.”

Reasonable Doubt

In her quest to regain her position as Sumner’s caretaker, Herzer has won a string of court rulings. In January, Dauman opposed her request that he be deposed. He lost. Redstone’s lawyers produced statements from doctors claiming he was competent at the time the decisions were made. They opposed Herzer’s request that her doctor examine him on an expedited basis. She won. On January 29, Dr. Stephen Read, a geriatric psychiatrist, examined Redstone. He made an audiotape, which is said by Herzer supporters to be particularly revealing of the seriousness of Redstone’s condition. (At the time of this writing, Read’s 37-page report has not been filed publicly, but the court was due to consider releasing it in mid-March.)

On December 11, 2015, Sumner sent a letter to Shari seeking to restore his relationship with her. “I love and trust you and your family,” he wrote. “You are all invited to stay with me and visit me any time. I am very sorry to hear that others have excluded you and your family from my house. That will never happen again.” Though this represents an abrupt reversal, Redstone states that he was under “no duress” in composing and signing the letter. It was witnessed by Jagiello and another of Redstone’s nurses.

On February 29, David Cowan, the judge in the case, wrote that Read found that Redstone “lacked mental capacity when he allegedly revoked” the directive that named Herzer as Redstone’s sole health-care proxy. Cowan found it hard to read the details “describing how this man is hanging on to life.”

While making the point that nothing had yet been decided about Redstone’s mental competence, Cowan’s ruling made a number of observations favorable to Herzer. He wrote that the case raises legitimate concern about who can best care for Redstone. He noted that, while Shari now is to be consulted about her father’s health care, “she still lives in Massachusetts—not around the corner—even with the ability to come here quickly.” He also questioned how much Shari had really “patched things up” with her father since Herzer’s removal from the house. Cowan found it “perplexing” that Redstone had put Dauman and Dooley “ahead of his own daughter as his agent in case of his incapacity,” and he wrote that he does not have confidence that things are quite as “patched up” as Shari claims. “It has to be an unusual situation where a parent still at this late date puts his East Coast business colleagues ahead of an adult child, or for that matter adult grandchildren, in terms of his care,” he wrote. Cowan also questioned Dauman’s ability to care for Redstone from New York. “The Court does not see how a person in charge of a public company in New York has the time or ability to look after Redstone even assuming his best of intentions,” he said.

In his ruling, Cowan also referred to an October 26 letter, written by Benjamin Ferrer, then a night nurse working for Redstone, who claimed to have overheard Jagiello making allegations about Herzer to Redstone. According to Cowan, Ferrer contended that Jagiello “had told Redstone that Herzer had lied to and stolen from him, and hence the reason for her forced departure, and further is exercising an undue amount of control over Redstone’s care.” The judge wasn’t sure whether Ferrer was just a “disgruntled employee” or if there was some truth in the accusations.

Needless to say, Redstone’s lawyers wanted Herzer’s case thrown out of court. And she won that ruling, too. She believes that the lawyers don’t legitimately have a client because Redstone is no longer mentally competent. Resolving the question of Redstone’s competence, Cowan noted, was hard to do, given Redstone’s lack of direct participation in the case. “A lot of things have been said about what Mr. Redstone wants, but unfortunately, I have no declaration from him…. It appears the person we’re all concerned about isn’t here.” On February 29, Cowan ruled that the trial would proceed, starting May 6. Herzer was subdued about this news. “Today’s victory is bittersweet,” she e-mailed me. “I’m still very worried about Sumner.”

In early February, the decision was made that Redstone should resign from his chairmanship of both CBS and Viacom. He did. In after-hours trading on February 3, Viacom’s stock rose to $49 a share, amid hopes that Dauman would not be named to replace Redstone as chairman of the Viacom board, especially since Shari had the right to succeed her father if she desired. That same day, Shari had supported Moonves to be the new chairman of CBS. But it turned out that she did not want to be chairman of Viacom, though neither did she want Dauman to have the job, and she voted against him. The Viacom board, which Dauman had cultivated for years, voted 10–1 in his favor, however.

A few days later, on February 9, Viacom announced that its fourth-quarter profit was down 10 percent and that its future revenue prospects would be hampered by lower fees from the cable and satellite companies that distribute its programming. Viacom’s stock had fallen some 45 percent in 2015, the worst performer in the S&P 500 Media Index. (The poor performance did not effect Dauman’s 2015 compensation, though. The board paid him $54 million, including a $17 million stock bonus for signing a new three-year employment contract.) When Dauman spoke in a conference call to Wall Street analysts, the stock collapsed, especially after he challenged an analyst who claimed that Viacom’s financial results were “exceedingly poor.” Instead, he said, “our outlook and the facts have been distorted and obscured by the naysayers, self-interested critics and publicity seekers.”

By the end of the day, Viacom’s stock had fallen 21.5 percent, slicing some $320 million off of Redstone’s wealth. Once upon a time, after a day like that, Redstone’s ire would have been white-hot. “Sumner, if the stock was down 5 percent, he would fire people,” a media executive says. “There’s no way he could have handled this.” Dauman would likely have joined the list of former Viacom chiefs Tom Freston, Mel Karmazin, and Frank Biondi.

But this time there was not a peep out of Beverly Park. In her court filings, Herzer described Redstone as a “living ghost.” For Freston, her description was not precise enough. “He looks like a corpse,” he says.

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