by Keach Hagey
* * *
Ultimately, though, it was not Shari’s manipulations but Sydney and Manuela’s fear of what Shari would do to them after Sumner died that led to their downfall. In the spring of 2015, Sydney and Manuela decided to go public with their relationship with Sumner by participating in a Vanity Fair profile by veteran investigative business reporter William D. Cohan. They saw the profile as a chance to show the world Sumner’s love for them and contempt for Shari, and thus create a bulwark against the likely challenge to their inheritance. Viacom spokesman Carl Folta thought it unwise, but he was overruled. Manuela and Sydney hired powerful spinmeister Mike Sitrick, founder of the preeminent LA crisis PR firm Sitrick & Co., and sat for formal portraits for the piece in red carpet–worthy evening gowns.
Given Sumner’s extreme difficulties speaking, Cohan would not be allowed to visit or interview him, but there would be an emailed question-and-answer portion that Shari knew Folta and Bishop were crafting Sumner’s answers for. Shari worried that they were “all out to do a major trashing of me in the story,” she wrote Tyler. “I don’t know what your grandfather will say. Probably whatever the women tell him to say.” If she didn’t have her lawyer and spokeswoman to protect her, she felt that she wouldn’t survive, she said, adding, “Because this is war.”17
Shari’s instincts were right. Octaviano got a peek at a draft of the questions and answers a few days later and reported back to Shari that they were not favorable to her. They said that the only family member who visited him was Keryn and that Sumner regretted giving Shari power at the company. He also reported seeing Sydney write notes for Sumner to read to Bishop over the phone about the article or dictate a sentence to him—“I kicked Shari out of the house”—that he repeated over and over again, preparing to tell it to Bishop.18 (People close to Sydney said this is not true.)
Ultimately, however, Bishop did not think that responses to the magazine criticizing Shari were a good idea. On April 9, a lawyer named Adam Streisand, who had worked with Bishop at Loeb & Loeb and had recently jumped to Sheppard Mullin, where he began representing Sydney and Manuela, sent an email to the women recommending that Sumner refrain from antagonizing Shari in his emailed interview. “The main concern by Viacom/Leah et al. is that if Sumner shames Shari publicly then Shari will seek to establish a conservatorship over Sumner,” he wrote. “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.”
When the email leaked a year later, Shari denied having ever considered conservatorship of her father.19 But the email stands as probably the single most damning piece of evidence that the people around Sumner—including Dauman, Tom Dooley, Shari, and Andelman, who were all on the boards of the public companies that Sumner controlled—likely knew that Sumner was unfit to serve on these boards nearly a year before he stepped down as the salary-drawing executive chairman of Viacom and CBS. At least two of these people—Dauman and Andelman—were among the trustees with the power to determine whether Sumner lacked the capacity to remain in control of the trust that held all National Amusements shares. According to the terms of Sumner’s trust, Sumner could be deemed “mentally incapacitated” only if he was judged “incompetent” by a court of proper jurisdiction, or if three doctors sent the trustees certification that he was “unable to manage his affairs in a competent manner.”20 And yet they never did it. So long as Dauman and his supporters, like George Abrams, were on the trust, Shari had no incentive to trigger it, since she would likely be outvoted in exactly the same way she had been on the Midway fiasco. And so long as Sumner kept signing off on ever-larger pay packages for Dauman, he had no incentive to take action, either. In the next couple of years, both Dauman and Shari would file lawsuits alleging that Sumner lacked mental capacity or was subject to manipulation. But for now, Sumner continued to pass the mental capacity tests that Bishop arranged, and the status quo rolled on.
In the end, calmer heads prevailed, and the Vanity Fair article—titled “Who Controls Sumner Redstone?”—did not contain any quotes from Sumner attacking Shari. But it was a meticulously reported bombshell nonetheless. Folta and Dooley went on the record for the first time about his health. “He’s lost some of his mobility in his jaw,” Dooley told Cohan, but he had been making strides working with a speech therapist. Folta added that “he can’t run out of a building,” confirming reports that he could not walk, but refusing to confirm rumors of his still-secret feeding tube. When the topic turned to Sumner’s mind, Dooley said, “He’s sharp as a tack.”
The most astonishing aspect of the story, however, came out of the mouth of Manuela, discussing how she and Sydney regarded their financial arrangement with Sumner. She told Cohan that when Sumner dies, she expects to be taken care of. “It’s such a fine line when you talk about money,” she said. “He considers me family and my children family. I mean, that’s his whole thing. He’s like, ‘You’re my family.’ You don’t pick your family in life, but Sumner Redstone does. He just does. He wants who he wants in his life.” She said he told her that he wants her to run his foundation when he dies, and she made clear she expects gifts in his will, for both herself and Sydney. “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,” Manuela said of Sydney. Sydney was “a good girl and she has his best interests at heart. For her, it’s a job almost, it’s a job.”21 (Sydney never looked at the relationship as a job, according to people close to her.)
Among the people shocked by the article was a forty-nine-year-old former actor and ex-con named George Pilgrim, who had been carrying on an affair with Sydney for nearly a year. Blessed with hunky good looks that helped him land roles on Guiding Light and Showtime’s erotic thriller Red Shoe Diaries, Pilgrim had had what he called an “extremely colorful” life, having served more than two years in prison, from 2006 to 2008, for his involvement in an advertising fraud scheme. From the beginning, he had known that Sydney was Sumner’s live-in girlfriend, having reached out to her on Facebook after reading a story in the Hollywood trade press in the spring of 2014 about her lawsuit against Naylor. Pilgrim had also been battling Naylor over her refusal to release her assistant from her contract so that she might join a reality show that Pilgrim was pitching, and Pilgrim thought he and Sydney could join forces. He sent his phone number, she called him, and by mid-2014, they were dating.22 She was so taken with his bad boy backstory that she optioned the autobiography he was writing, Citizen Pilgrim, for her production company, Rich Hippie Productions. She bought a $3.5 million house in Sedona, Arizona, where he had been paroled to his parents’ house, and he soon moved into it. They joined a country club together, flew back and forth by private jet, sent each other sexually explicit texts, and talked of marriage. In late 2014, Pilgrim sent her emojis of a family, a ring, and a bride, and then called her to propose. He later texted, “Is that yes?” and she replied “yes yes,” followed by a string of heart emojis. Around this time, Sydney asked him to donate his sperm and tried to get pregnant via in vitro fertilization. A devotee of New Age spirituality, she arranged black tourmaline crystals around the Sedona house to ward off bad luck. They must have worked: at one point, Jim Elroy, the former FBI agent whom Shari had hired to investigate the women, called the house, but Shari never took any action to expose Sydney.
Meanwhile, Sydney told Pilgrim that her relationship with Sumner was not romantic. He was her “mentor,” she said, and she was in charge of his health care. When Pilgrim got impatient, texting her to run away with him, Sydney replied, “Yes please.” “Waiting for a man to die!!! Fuck that we can be explorers travel the world Indiana jones stuff,” Pilgrim texted. “I know,” Sydney responded. “It sucks for both of us I am sorry.” To make sure she got her inheritance, she told Pilgrim that she had to be vigilant about not leaving Sumner alone with his family. “Listen I can barely leave the house,” she told h
im, later adding that “he is old and crying all the time,” but Sumner’s family “won’t be able to do much I will be here the whole time and so will pitbull,” Sydney and Pilgrim’s nickname for Manuela. When Kim came to visit, Sydney snapped a photo of her watching television with Sumner and texted it to Pilgrim, saying, “It’s so fake and phony, she is such a little spy and I am not leaving this room.”
Given Pilgrim’s assumptions about their relationship, when the Vanity Fair story came out quoting Sydney rhapsodizing about how Sumner has “this beautiful hair” and “the most beautiful skin I’ve ever seen in my life,” Pilgrim flew into a jealous rage. He was drinking heavily, and by May 2015, Sydney had convinced him to check himself into a rehab facility outside Austin, Texas, with her mother as his sponsor. While he was in there, she kicked him out of the Sedona house. When he found out about that, he broke out of rehab, flagged down a taxicab, and talked the cab driver into driving him eighteen hours back to Sedona. They broke up, and soon lawyers got involved. Sydney wanted Pilgrim’s silence, and Pilgrim wanted Sydney’s millions. Their lawyers batted dollar figures back and forth, and by August, a $10 million settlement was on the table that would have given Pilgrim a share of the proceeds from the Sedona house and a chunk of Sydney’s inheritance from Sumner, so long as he and the people close to him signed nondisclosure agreements.
But in late August 2015, Pilgrim, who is bipolar, had grown impatient with the talks. One night he and his former girlfriend, with whom he had gotten back together after he and Sydney broke up, wandered into the posh Beverly Hills wine bar Wally’s, which was owned by a group of investors that included the family of Manuela’s daughter Christy’s boyfriend, Matt Marciano, the son of Guess? Jeans cofounder Georges Marciano. They found themselves seated next to Manuela, her son, her daughter Christy, and Marciano. Pilgrim knew who they were, but they didn’t know he existed. As he listened to their banter, he began to wonder whether he was doing the right thing. A week later—two days before his settlement was supposed to go through—he was invited to a party at Wally’s where he saw Marciano again. This time, he decided to blow it all up. He introduced himself to Marciano as Sydney Holland’s fiancé, and showed the photos on his phone as proof. Word got back to Manuela, who was angry at having been kept in the dark about Pilgrim, and everyone involved decided that Sydney had to come clean. On August 30, 2015, Sydney and her high-profile attorney, Patty Glaser (who is Robert Shapiro’s law partner), sat Sumner down and told him about Pilgrim. By the end, both Sydney and Sumner were in tears. Within forty-eight hours, she and Alexandra were gone.23
Manuela consolidated power immediately. On September 3, Sumner called in Bishop, wrote Sydney out of his will, and boosted Manuela’s bequests in the will to $50 million in addition to his Beverly Park mansion, worth an estimated $20 million. (Sumner had already made Manuela the joint tenant on his $3.75 million Carlyle Hotel apartment so she would inherit it when he died.)24 He also removed Sydney as his health care agent, so that now Manuela held the role alone. Dauman was named as the alternate. In court documents, Manuela held up the fact that Sumner did not choose members of his own family for this role as evidence of Sumner’s estrangement from Shari.25 To make sure the changes stuck, Bishop called in geriatric psychiatrist Dr. James Spar to administer a mental capacity exam, which Sumner passed.26 She later told the Wall Street Journal that this was done “to safeguard against meritless challenges.”27
Manuela knew she would need backup for her new role. The day after Sydney left, she called Keryn, who for months had been discussing moving from Colorado to Los Angeles, and told her to move immediately. Keryn’s presence in the house meant that, among other things, Manuela couldn’t be accused of barring Sumner’s family from seeing him. But Keryn was a safe ally for Manuela because she might have been the one person on earth who hated Shari more than she did. Keryn had been fighting with her own parents, Brent and Annie, over the trust that they set up for her, and she had not yet passed the bar, so she needed financial help with the move. Sumner agreed to loan her his credit card for moving expenses, hotels, and food, she said in court documents. Soon after she arrived, on September 9, Sumner set up a $1 million trust in her name, with Manuela as the trustee.28 She wasn’t allowed to touch the principal for twenty years, but she could live off the income. To help her through her immediate financial problems, Sumner agreed to give her $15,000 in 2015 and $15,000 in 2016 and told her, according to Keryn, “You can have any job you want.”
When she first got to LA, Keryn found Sumner agitated and angry, obsessed with seeing pictures of George Pilgrim and bulking up his mansion’s security after Manuela told him that Pilgrim and Sydney were plotting to kill him. But he also just cried a lot. Soon he became obsessed with a woman named Terry Holbrook, a sixty-year-old former Ford model and Dallas Cowboy cheerleader whom he had known since 2010. Holbrook said he had been sponsoring her two show horses for years, adding, “He’s been a savior in my life.” Manuela claimed Holbrook had received some $7 million from Sumner since 2010, including a house and monthly payments of $4,500, which Sumner’s driver would leave for her at the Beverly Park guard gate. According to Keryn, Holbrook’s visits were arranged by Jagiello, one of the nurses who was secretly loyal to Shari, who would “translate” Sumner’s grunts to Holbrook during their encounters. Over time, Keryn alleged that Jagiello controlled Sumner through his access to Holbrook. Sumner’s obsession grew so intense that he would sometimes ask for her multiple times a day, forgetting that he had already done so.29
Manuela was wary of Holbrook. According to Sumner’s lawyers, she had Sumner’s doctor tell him that he was only allowed to have sex once a week. When he insisted on seeing Holbrook anyway, Sumner’s lawyers claim Manuela made up excuses why she could not come—she was sick, her mother was sick, she had to cancel at the last minute. Holbrook says these were never true. “I told him, ‘If somebody tells you that I can’t see you, they are lying,’” she said.
Most important, Manuela wanted to keep Sydney away. When, in early October, Sydney’s lawyer asked Bishop to hand-deliver a letter for her to Sumner in which she profusely apologized for her infidelity and professed her love, Manuela intercepted the letter and replaced it with one she wrote herself. According to Sumner’s lawyers, the letter read:
Sumner
I did not lie to you everyone else is lying I never had an affair with that man
It’s not true people are just trying to break us up.
You have to believe me I never lied to you I don’t know who he is.
Don’t understand why you don’t believe me and you believe everybody else.
Sydney
Sumner’s lawyers claim that Manuela had the nurses read Sumner that letter instead of the real one.30 Manuela, in a separate lawsuit, appears to claim that the draft of that letter was planted on her computer by Shari’s allies.
Meanwhile, Jagiello was eavesdropping on happenings in the house and sending word back to Tyler. According to Manuela’s complaint in one lawsuit, Jagiello even recorded meetings between Sumner and Manuela and Bishop and Dr. James Spar, the geriatric psychiatrist whom Bishop used to give Sumner mental capacity exams, sent the information to Shari and her lawyers. The complaint also alleges that Jagiello got an email address and password from Sumner’s driver, Isileli “Isi” Tuanaki, and used it to log on to Manuela’s email and the video recordings of the network of cameras that the women—they claimed at Sumner’s request—had set up around the house.
On September 18, Jagiello and Tyler texted about their plans to oust Manuela from the house.
“Good morning,” Jagiello texted Tyler. “Thanks for talking last night. Seal team commence operation freedom today! FYI! I will keep you posted . . .”
“Ha it kinda does take seal precision! Thanks for the update,” Tyler replied.
“Let’s hope this goes well. SMR asked me same question this am. Once he knows the truth he is going to be livid! . . . Also do you think it is a good idea to take
video footage of Manuela/Keryn post reveal while shit hitting the fan for everyone’s protection? Also Philippe working closely with Manuela,” Jagiello wrote.
“Video can’t hurt (unless you’re caught!) . . . may also help protect you if M [Manuela] fires anyone against smr wishe[s].”31
When Manuela’s ouster did finally come, her response would rock the Redstones’ global empire to its foundations.
Chapter 21
Sex and Steak
By October 2015, Sumner’s silence on Wall Street was deafening. He had not spoken on an earnings call in nearly a year and attended neither Viacom’s nor CBS’s annual meetings that year. Meanwhile, media stocks had tanked in August after Disney CEO Bob Iger said that ESPN—long considered so essential to pay-TV distributors that it could charge them a stunning $7 per subscriber,1 many times more than any other channel—had experienced “some subscriber losses.” Investors took those words as confirmation of their long-held fears that the cable bundle was coming apart. Viacom, having delivered disappointing earnings, was hit hardest. By early October, its stock had dropped more than 40 percent over the past year.
For longtime investors who had watched Sumner fire CEO after CEO following far more modest drops in Viacom’s stock price, Dauman’s continued employment seemed clear evidence that Sumner was no longer himself. At one point, Shari had been so distraught over Dauman’s performance that she went to him directly and said they both knew he was not the right person to lead the company. (Dauman replied that he didn’t intend to be CEO for life, but the company had some key affiliate deals coming up that he felt were important for him to be involved in.) When that didn’t work, she went to the committees of the board, begging them to get rid of Dauman. But Viacom’s board was stacked with Sumner intimates like George Abrams and William Schwartz, who had been there since Sumner took over the company in 1987. Those who did not fall into this category had little leverage. Unhappy with the direction of the company but concluding there was little he could do about it under the current governance structure, Bob Kraft, Shari’s ally, left the board in August.