But Redstone was just warming up. He told King he worked out 50 minutes every day, without fail, usually by swimming in the nude in one of the pools on his sprawling estate, in the Beverly Park section of Los Angeles. He is careful about what he eats. “I eat and drink every antioxidant known to man,” he said. That includes “goji berries, Green Machine smoothies, and tomato juice.”
And then there was the sex. “I feel better than I did when I was 20,” he continued, “in every facet,” even sexually.
Almost five years later, he still believed he was immortal. Asked in his last public interview, in January 2014, with The Hollywood Reporter, about who might succeed him, he exploded, “I will not discuss succession. You know why? I’m not going to die.”
But Redstone’s immortality, or lack of it, is of immense importance to Philippe Dauman, the C.E.O. of Viacom, and Les Moonves, the C.E.O. of CBS, and their executive teams as well as to shareholders of the two companies, because Redstone controls the majority of the voting shares of both. Should his bravado fail to impress the Grim Reaper, a series of events will be set in motion that could lead to the sale of CBS or Viacom or both and dramatically change the calculus in Hollywood. Needless to say, with so much at stake, nearly everyone involved—including Redstone’s 43-year-old live-in girlfriend, Sydney Holland, his close friend and former girlfriend, 50-year-old Manuela Herzer, and his daughter, Shari Redstone, a 61-year-old divorced mother of three, whom Redstone once called his heir apparent only to change his mind later—is jockeying for position as the king fades. “No one seems to have any definitive view on what happens,” says a longtime Hollywood executive.
In the meantime there are widely diverging accounts of the state of Redstone’s health. To address the question, the easiest thing would be to allow me a visit with him at his mansion. But Redstone is off limits to outsiders these days. For the first time in anyone’s memory, he did not attend the Viacom annual meeting, in Miami on March 16. But he is planning to attend this year’s CBS annual meeting, in New York on May 21. He attended CBS’s annual meeting last year, in Los Angeles, but only briefly, when, hidden by a curtain, he was carried onstage in a chair. He was on the November 2014 Viacom earnings call, but barely. His faint voice could be heard introducing Dauman: “Good morning, everyone. Here’s my wise friend Philippe.”
His public appearances are few and far between, relegated to quick, late-afternoon dinners at such Hollywood standbys as Dan Tana’s, Craig’s, and Il Piccolino. At Il Piccolino his eating habits, which include liberal use of his hands, were described as so uncouth he was known as the Beast. “I’m tired of going out to dinner with him and having him mistreat the waiters,” says a friend. “He’ll scream at them, usually trying to prove a point.” But Redstone doesn’t want anyone talking about his restaurant visits, which used to be regular fodder for the New York Post’s “Page Six.” “We had already from him, how do you say, a lawsuit, nearly a lawsuit, so I cannot say anything,” explains Silvio De Mori, one of Il Piccolino’s owners. “We do not have his money. We cannot fight on trial.”
Redstone still spends time with longtime friends such as Robert Evans, the legendary movie producer whom Redstone once described as his “closest friend on the creative side” of Hollywood. But now Redstone is said to be miffed that Evans dedicated his latest book, The Fat Lady Sang, to Graydon Carter, the editor of this magazine, instead of to him. “Like everybody else, Sumner has good days and bad days,” says Evans, who can’t get off the phone fast enough when asked about Redstone’s health. “I really don’t want to talk about him.”
In written answers to 20 questions from V.F., Redstone claims his routine hasn’t changed much. “I still get up at 4:30–5 a.m. every day I ride my bike and go to the pool and get a haircut. I’m really into watching sports.”
A person who was visiting with Bob Evans recently broached the topic of Redstone’s health. “He looks like he’s dead,” he told Evans, who is said to have replied, “Well, you should see him in person—he looks even worse.”
Regarding the question of Redstone’s feeding tube, Folta says, “We are not going to comment one way or the other because we respect Sumner’s desire to keep private specific information about his health.” Adds Leah Bishop, one of Redstone’s outside estate-planning and tax attorneys, “Based on face-to-face meetings—because it is very difficult to speak with him on the phone, his speech is impaired—he not only understands the subject matter of what we’re discussing and the importance of the documents he signs but he is engaged and responsive.”
Sydney Holland, nearly 50 years younger than Redstone, has been living with him for the past few years. In a wide-ranging interview, her first ever about Redstone, she declines to comment on his condition. “Those are questions you’re going to have to ask him.” She does allow, though, that “he’s doing good. He’s very sharp. He remembers everything, everything.” Adds Manuela Herzer, in a separate long interview, “He’s physically good.”
SPRINGTIME FOR SUMNER
By 1980, National Amusements had bought meaningful equity stakes in Fox (then owned by Denver oilman Marvin Davis), Warner Communications, MGM Films, Columbia Pictures, and Time, Inc. Redstone would often visit Los Angeles and set up shop at the Beverly Hills Hotel.
In 1987, National Amusements won a heated battle to take over Viacom, the global mass-media company that owned radio stations and had majority stakes in MTV Networks and Showtime. Wall Street was aghast that an unknown had captured the company. Seven years later, in an epic and well-documented battle, Redstone and Viacom bought Paramount Communications for $10 billion, and then Blockbuster Entertainment, the movie and video-game rental company, for another $8 billion. The cast of combatants included the most prominent names in the media business, among them media and telecom investor John Malone and Barry Diller, then the chairman of QVC. “Look, I just want to win,” Dooley, then Viacom’s treasurer, remembers Redstone arguing throughout. “I don’t care what we bid. I just want to win…. I just want to beat Barry.”
In 2000, Viacom bought CBS for $40 billion. In 2006, Redstone split Viacom and CBS into two separately traded public companies, with Viacom run by Dauman and CBS run by Moonves. Redstone controls both companies through his 80 percent ownership of National Amusements. (Redstone’s daughter, Shari, controls the remaining 20 percent.) In turn, National Amusements owns 79.7 percent of CBS’s voting stock and 79.5 percent of Viacom’s.
Redstone’s controlling stake in the company is protected by a generation-skipping, irrevocable confidential trust, of which there are seven trustees, according to a recent CBS public filing, including Redstone, his first wife, Phyllis, and Dauman, as well as a group of Boston lawyers with longtime ties to the Redstone family: George Abrams, David Andelman, Norman Jacobs, and Leonard Lewin. When Redstone leaves the scene or is incapacitated, according to the trust document, Shari and her son, Tyler Korff, 29, a lawyer and rabbi, will become trustees. Phyllis, although she will remain a trustee, will no longer vote on matters involving Sumner’s 80 percent stake in National Amusements.
Reportedly, in 2002, as part of the divorce settlement with Phyllis, whom Redstone had married in 1947 and who filed for divorce in 1999, the trust agreement stipulated that Shari would succeed her father as board chairman of both Viacom and CBS. But Redstone has had second thoughts about those decisions, and it is no longer clear that will happen. Shari now serves as vice-chairman of both boards. For a while, she and her father were communicating only through faxes. In 2007, Redstone offered to buy her 20 percent stake in National Amusements, but she declined to sell. She remains titular president of the company but no longer has a day-to-day management role. Instead, she spends her time at Advancit Capital, a venture-capital firm she co-founded with her son-in-law Jason Ostheimer. She obviously has a major interest in how things unfold at CBS and Viacom in the post-Sumner era, and executives at both companies are careful not to offend her.
Some press reports have speculated that Moonves is talking to private-equity sources about trying to take CBS private before Redstone dies or that he is thinking seriously about buying the National Amusements stake in CBS and still keeping it a public company. And then there is the persistent rumor that Viacom and CBS will be re-united, although the prospect of Dauman and Moonves working together seems remote at best. Some have suggested that, because Viacom has been struggling operationally of late, a combination with CBS would be a nice exit strategy for Dauman, who would turn over the reins to Moonves. Both men busily reject the merger speculation. “We are feeling pretty strong about ourselves and don’t need any partners,” Moonves said in a CBS earnings call. In March, Dauman told investors, “We have no intention of buying CBS or buying any other big company out there.” (CBS declined to comment on any aspect of this story.)
Nevertheless, Wall Street can’t help but salivate. Mario Gabelli, a longtime money manager whose clients include the second-largest investors in the CBS and Viacom voting shares, says about Redstone, “My prayers are with him. Look, everybody tells me that when he can’t get on a conference call there’s an issue. When the management says, ‘He’s listening,’ I’m sure he is.” Gabelli says he personally is no fan of recombining Viacom and CBS. “Philippe and Les are oil and vinegar, and I want to keep them both,” he says. “You can’t put them together.” He says when Redstone dies the questions facing CBS and Viacom will be unchanged.
That is still a long way off, according to the Viacom team, which says Sumner still speaks with Dauman “three or four” times a week. Dooley and Folta say they visited with Redstone at his house a few months ago. “He was fine,” says Dooley, “sitting there waiting for us to come in.”
THE BACHELOR
Soon thereafter, Bob Evans decided to fix Redstone up with beautiful women. At one dinner party at Evans’s house, Redstone maneuvered himself next to Manuela Herzer, a gorgeous Jewish divorcée of Argentinean descent. Herzer’s late paternal grandparents, both doctors, owned “a lot” of Buenos Aires real estate. Her father moved the family—Herzer has four brothers—to Miami when she was two years old. She went to school in Paris and speaks French, English, and Spanish fluently. In Paris, she dated Eric Chamchoum, the scion of a wealthy Lebanese family. They got married and had two children, now in their 20s, before divorcing. Back in Los Angeles, a short relationship resulted in a daughter, Kathrine Herzer, now 18, who plays Alison McCord, the daughter of secretary of state Elizabeth McCord (Téa Leoni) on the hit CBS show Madam Secretary.
As his second marriage faltered, Redstone got back in touch with both Peters and Herzer. He told Herzer he had a “horrible relationship” with Fortunato; he told Peters, “I’m so unhappy. I’m so unhappy.” Herzer comforted him. “Sumner, you worked your whole life,” she told him. “You should be the happiest man on earth right now. You should do whatever makes you happy.” Lots of other Hollywood women wanted to date him. He wanted to rekindle the relationship with Herzer, she says, but she was not interested in starting things up again as before. “He’s such an important person in my life,” she says. “I just didn’t want to be married.”
Instead, he would take Herzer to dinner parties and ask her opinion of the women in whom he was interested. Eventually she tired of this responsibility. “This is humiliating and embarrassing,” she told him. In 2010, Patti Stanger, the host of the hit Bravo reality show The Millionaire Matchmaker, introduced Redstone to her longtime friend Sydney Holland, according to Holland. Redstone soon took her to Catch, a seafood restaurant in Santa Monica. Stanger, who also has an off-camera matchmaking business, thought Holland and Redstone would hit it off because, Holland says, “Sumner has an amazing sense of humor and a quick wit and is incredibly intelligent, and she knows that that’s the kinds of things that I like.” Redstone asked Herzer’s opinion of Holland. She approved. “I was like, ‘You know, this girl can’t be so bad,’ ” Herzer says. “Do I know anything about her background? Nothing, and I don’t care, because why do I need to judge her? I’m not dating her.’ ”
Holland, in fact, does have a complex backstory. She grew up privileged in La Jolla, California. Her father, a cosmetic dentist, pioneered the use of veneer to improve the look of teeth. Her mother is a social worker in Los Angeles, specializing in interventions. Holland graduated from La Jolla Country Day School, and although she was accepted to U.S.C. she decided instead to “jump into” the fashion business. She started a line of “eco-conscious” yoga clothes before deciding to open a dating service.
In the February 2004 issue of Los Angeles magazine, on page 221, there is an advertisement for “The Inner Circle VIP social club” with a picture of Holland—using her birth name, Sydney Stanger (no relation to Patti)—and Corinne Cliford extolling the “New Matchmakers in Town!” and offering “a first class dating service for exclusive gentlemen and exquisite ladies who seek to meet the love of their life!”
THE AGE OF INNOCENCE
A year or so after Holland met Redstone, she says, he asked her to move in with him. Holland was thrilled. “He likes to have someone near him all the time,” she says. “It was just a natural thing that happened.” They have been together ever since.
Fortunately her money woes soon disappeared. She began a slew of new business ventures, with decidedly mixed results. In 2012 she started Rich Hippie Productions, an independent film financing and production company. Among other projects, Holland announced she was to be the executive producer of a feature-length film directed by Michael Polish and starring his wife, Kate Bosworth.
Holland hired Erik Fleming, an independent producer and director, and then promoted him to be the company’s president. But he has since left Rich Hippie, and Holland has not replaced him. Rich Hippie, she says, is no longer “my main focus.” The same goes for UnSpoken, a now defunct lingerie company she invested in with founder Caron Block. “Being in the garment business is a lot of time for not as much profitability that I was expecting,” Holland explains.
As of late, Holland is in the business of buying, renovating, and selling Los Angeles real estate. She says she has flipped three houses so far: one, which she sold last October for around $8.2 million to actress Jennifer Lawrence, made all the newspapers. Holland had bought the 5,500-square-foot house in 2013 from singer Jessica Simpson for $6.4 million.
Then there is the Sydney D. Holland Foundation, which focuses on helping at-risk youth and preventing substance abuse among women and children. I.R.S. records show that in 2012, the year the foundation was established, it had gross receipts of less than $50,000. “I’m not going to discuss how much money my foundation has,” Holland says. “We do a lot of good work, and I sit on a lot of boards, and I do a lot of things that are non-monetary as well.”
In an e-mail to Vanity Fair, Redstone writes, “I love Sydney and Alexandra.” Herzer, who is godmother to Alexandra, says Holland’s relationship with Redstone is “the best thing that’s ever happened to him.” She adds, “He is so happy with her. Sydney is misunderstood in a sense because she’s the one person who really cares about him…. He’s blessed to have her. And when people say that she’s controlling him—I said that to my son the other day, and my son started laughing. He said, ‘Well, those people must not know him.’ No one controls Sumner, not today, not tomorrow, not ever.”
But there is a growing sense that the two women are managing more and more of his life. One person, who has known Redstone for years, wondered why Tom Dooley, at Viacom, or members of the Redstone family have not tried to intercede. “Why is nobody doing this?” this person asked. Though Redstone, in an e-mail, insists otherwise, another person wonders whether he is capable of understanding legal documents that are put in front of him. An insider in Redstone’s business empire notes that e-mails and faxes from Redstone to executives at Viacom and CBS, sent out through his secretary in New York, are so different from what he used to get from Redstone that he is puzzled. “It has always been my practice to dictate correspondence, which I continue to do through assistants and others designated by me,” Redstone writes in an e-mail.
Portions of an ongoing struggle for control of the Sumner Redstone endgame broke into the open in August 2013 when Holland sued Heather Naylor, a bombshell former star of the short-lived MTV series The Electric Barbarellas, who, like so many other attractive women, had supposedly taken a shine to Redstone and vice versa. Holland alleges that her laptop computer went missing from the Redstone mansion in 2011 when Naylor was visiting. The laptop had on it personal e-mails and photographs. Holland says there are pictures of her late father and objects to speculation that there is anything more sensational. She confronted Naylor, who denied having the laptop. Some two years later, Holland further alleges, on June 12, 2013, when Holland was at the hospital, picking up the newborn Alexandra Red, Naylor visited Redstone’s house with a computer. Holland alleges that Herzer was there at the time and saw Naylor printing out some of the content and sharing it with various people present and then boasting that she had “so much more.” Holland again demanded that the laptop be returned, but Naylor continued to deny that she had possession of it. Holland has sued Naylor for $1 million in damages.
In her response to Holland’s suit, Naylor denied that she had the laptop, and she countersued Holland. Naylor claimed that Holland had turned Redstone against her and ruined her career at MTV. She alleged that after she had lunch with Redstone on June 12, 2013, Holland “grew jealous” and “cut off all ties” between Redstone and Naylor, even taking her name out of his address book. Naylor further alleged that Holland was taking total control of the Redstone household—by firing and replacing long-serving employees, by cutting their compensation, by having them submit to polygraph tests, and by forcing them to sign confidentiality agreements. Concluded Naylor, “Holland has effectively taken over Redstone’s life and does not allow anyone independent access to him.” (Naylor has since dropped her lawsuit against Holland, but Holland’s suit against Naylor continues and is moving toward a trial.)
Although she declines to answer questions directly related to the lawsuit, Holland denies she has forced employees to take lie-detector tests. She also denies firing long-serving staff. “Sure, I help hire new staff,” she says, “but they’re all Sumner’s decision. Everybody that works for Sumner, he decides who works for him…. No one tells Sumner Redstone what to do ever, not me and not anybody.”
Then there is the story of a rare visit, in September, by Shari and her son Tyler that ended in Redstone throwing them out of the house.
In one version, Herzer and Holland were out shopping together and knew that father and daughter were at the house. At some point during the visit Shari abruptly ordered one of the house staff out of the room. “So the guy calls Sydney, and he’s like, ‘Why is this lady so rude?’ blah, blah, blah,” says a person close to Holland and Herzer. “And Sydney went to call Sumner, and Shari kept hanging up on Sydney, and that was the story. That was it. And Sumner was like, ‘What’s going on here? Why are you hanging up on her? Get out.’ ” A spokesperson for Shari rejects this version of events but confirms that Sumner ordered Shari and Tyler out of the home.
The person close to Holland and Herzer says Redstone has thrown Shari out of the house “100 times” and that their relationship is deeply strained by the fact that Shari simply does not appreciate that her father likes younger women around. “It’s unfortunate that he feels like that about [Shari], but it’s something that’s out of everyone’s hands,” this person continues. “She’s never liked one person—after the mother—that Sumner’s with or anything. She likes them because she has to.” This person says it’s vital to Shari for her to be seen as her father’s heir apparent and yet they have very little interaction. “I can understand it if you love your father and you treat him with respect and you come visit him. [But] you don’t drive by Beverly Park to go to a CBS board meeting that he put you on the board of and not say hello. He’s your father, for God’s sakes.” (Shari’s spokesperson replies, “The comment that Shari has been ‘thrown out of the house hundreds of times’ is totally false. She and her children have enjoyed warm and loving visits with her father.”)
Needless to say, the relationship between Shari and the two younger women is strained. “They have a very contentious relationship, and that’s no secret,” says someone who knows them all.
“There is nothing more important to me than my family,” says Shari. “I’m not going to publicly comment on my father’s two current female companions or their impact on our family.”
WHERE THERE’S A WILL THERE’S A FRAY
Herzer says that she would also be shocked if Holland is not a beneficiary of the will. “It would be almost disgusting if he didn’t do what everyone says he’s doing and going to do,” she says. “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. I don’t have a doubt in my mind.” She assures me that Holland “is a good girl and she has his best interests at heart. For her it’s a job almost, it’s a job.” Still, Herzer says, if Holland finds herself cut out of Redstone’s will, Holland will be fine. “I know it’s hard to believe,” she says, “because I’ll tell you why. Because up to now she’s had a great life. She has a great life. She lives in a beautiful mansion. She has beautiful things.” Meanwhile, as Redstone approaches his 92nd birthday, preparations are probably under way for a lavish celebration. If it’s anything like the party for his 90th, the guests may be treated to a private concert by Redstone’s friend Tony Bennett, who credits him with reviving his career.