"Waiting for a Man to Die!!!" Inside the Fall of Sumner Redstone's Girlfriends

For years, Sydney Holland and Manuela Herzer ruled the aging Viacom-CBS mogul's L.A. mansion, until a medical crisis, a secret fiance and some frantic texts gave Shari Redstone a path to regain control of her father’s empire, reveals this exclusive excerpt from Wall Street Journal reporter Keach Hagey's new biography of the media mogul.
David Crotty/PatrickMcMullan.com
 From left: Manuela Herzer, Sumner Redstone and Sydney Holland at a gala in March 2013 honoring Al Gore.

In September 2014, Sumner Redstone’s health took a dramatic downturn from which he never fully recovered when, at age 91, he was hospitalized with aspiration pneumonia from inhaling food into his lungs. That crisis set the stage for the fight over who would seize control of his companies Viacom and CBS that is still playing out today. As Wall Street Journal reporter Keach Hagey details from interviews and court records in this excerpt from her new biography of Redstone, The King of Content, the first act of that drama was the dissolution of his relationships with Manuela Herzer, then 50, and 43-year-old Sydney Holland. These live-in girlfriends had long controlled access to him, until Shari found a way to regain control of her father’s personal and corporate holdings.

Sumner returned from the hospital to his Beverly Park compound a shadow of his former self. He could not stand on his own. He required a catheter. He would never eat another meal again. And perhaps worst of all, the aspiration had, according to Manuela, caused brain damage that left his speech limited almost entirely to monosyllabic grunts. He was more dependent on Manuela and Sydney than ever, and Shari’s hostility to them only made him push her farther away. “I just called to tell him that I love him and that I would be there tomorrow and all he kept saying was, ‘Leave Sydney and Manuela alone,’” Shari wrote her children Sept. 15. “He said it 100 times. He was not interested in the fact that I love him or that [her son] Tyler and I were coming out.” The next day, Shari and Tyler came to visit Sumner at his mansion while Sydney and Manuela were out. Things quickly got tense when Sydney called the house, telling Sumner to ask his family to leave. He did. Joseph Octaviano, one of his nurses, wrote Shari an email later that day saying that incident was typical of the way he had seen the women treat Sumner, adding, “One time Manuela told your dad that none of his family loves him except them.”

As Sumner ratcheted up the pressure, begging Shari to sign legal releases promising not to go after the millions he gave Manuela and Sydney to give him “peace of mind,” Shari dug in. “Why would I ever give SMR his dying wish of peace when he never gave me any peace during my whole life?” she emailed Tyler. “Going after those [women] will give me peace. They should get what they deserve.” She hired a private investigator to research their pasts and emailed Tyler, “In one week we sure have them pegged based on background.”

On Jan. 29, 2015, some of Sumner’s nurses and household staff filed a report with Los Angeles County Adult Protective Services, alleging that Sydney and Manuela had been mentally and financially abusive. January had been a brutal month in Beverly Park, filled with crying and screaming from Sumner, as the fight to get Shari and the family to sign the releases reached its climax: a letter from Sumner threatening to bar them from his funeral unless Shari signed.

Through it all, Octaviano’s emails provided behind-the-scenes information. On that same day, Sydney met with estate planning attorney Leah Bishop and Sumner at around 11 a.m. By 11:30, Octaviano wrote, he could overhear Sumner crying during the meeting. Sydney told Octaviano that Sumner was not to receive phone calls from the family, “especially Shari and Kim” [Shari’s daughter]. Kim finally got through and Sumner told Sydney that he had told Kim that she and her two young children were welcome to visit anytime; Sydney got angry, saying Kim was a liar just like the rest of the family. Sumner screamed, “I love Kim!” prompting more screaming from Sydney.

These incidents fit into a broader pattern of abuse outlined by nurses in sworn declarations for later litigation. In their telling, Sydney and Manuela spent a great deal of time coaching Sumner on what to say, sometimes writing a script in large letters on a note pad so that he could memorize his lines before estate planning meetings. They woke him up to have him sign cash withdrawal forms or legal documents when he was groggy. And during sensitive meetings with the women about money, the nurses were sent from the room but often overheard Sumner crying; when the meeting was over, they would come back in to find Sumner had gotten so upset that he had soiled himself and had been sitting like that for at least half an hour. Sydney believes these anecdotes are fabrications by the nurses who were on Shari’s payroll. In Manuela’s legal filings, she argues that one got $10,000 from Shari and in one email to Shari, Octaviano angled for help buying a house.

Adult Protective Services sent an investigator to the house. Sydney, who was out of town, instructed staff not to let him in, and instead to ask them to make an appointment for later. When the investigator returned he found Sumner surrounded by the women and lawyers, including Robert Shapiro, best known as a member of O.J. Simpson’s legal team. He only spoke to Sumner, the women and the lawyers, not to any of the nurses, staff or family, and never took action on that complaint.

Ultimately, though, it was not Shari’s manipulations but Sydney's and Manuela’s fear of what she 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 reporter William D. Cohan. They saw it 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 crisis PR spinmeister Mike Sitrick and sat for formal portraits in red-carpet-worthy evening gowns.

Among the people shocked by the article was a 49-year-old former actor and ex-con named George Pilgrim, who had been carrying on an affair with Sydney for nearly a year. 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 in the spring of 2014 after reading a story about her lawsuit against aspiring singer/reality star and Sumner girlfriend Heather Naylor. Pilgrim had also been battling Naylor over her refusal to release her assistant from her contract to join a reality show that he was pitching. Pilgrim thought he and Sydney could join forces and by mid-2014, they were dating. She was so taken by 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, Ariz., where he had been paroled to his parents’ house, and he soon moved into it. They joined a country club together, flew 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. Sydney also asked him to donate his sperm and tried to get pregnant via in vitro fertilization.

Meanwhile, Sydney told Pilgrim 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.” Pilgrim texted back: “Waiting for a man to die!!! Fuck that we can be explorers travel the world Indiana jones stuff.” To make sure she got her inheritance, she told Pilgrim that she had to be vigilant. “Listen I can barely leave the house,” she told him, 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's and Pilgrim’s nickname for Manuela.

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,” he flew into a jealous rage and they broke up. Soon lawyers got involved. Sydney wanted Pilgrim’s silence, and Pilgrim wanted Sydney’s millions. By August, a $10 million settlement was on the table that would have given him money from the Sedona house and a chunk of Sydney’s inheritance from Sumner as long as he and those close to him signed nondisclosure agreements.

But Pilgrim had grown impatient. One night he and his former girlfriend, whom he had gotten back together with, found themselves at the Beverly Hills wine bar Wally’s seated next to Manuela, her son, her daughter and her daughter’s boyfriend, Matt 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 cutting a deal with Sydney. 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 fiance. Word got back to Manuela, who was angry at having been kept in the dark about Pilgrim. Everyone involved decided that Sydney had to come clean. On Aug. 30, 2015, Sydney and her high-profile attorney, Patty Glaser, sat Sumner down and told him about Pilgrim. By the end, both Sydney and Sumner were in tears. Within 48 hours, she was gone.

Manuela consolidated power immediately. Bishop wrote Sydney out of Sumner’s will and boosted Manuela’s bequests to $50 million. She also removed Sydney from her role as his health-care proxy. Manuela knew she needed backup for her new role. The day after Sydney left, she called Sumner’s granddaughter Keryn, who for months had been discussing moving to Los Angeles. Keryn’s presence in the house meant that among other things Manuela couldn’t be accused of barring Sumner’s family members. But Keryn was a safe ally because she might have been the one person on Earth who hated Shari more than Manuela. When she got to L.A., Keryn found Sumner agitated and angry, obsessed with Pilgrim and bulking up the mansion’s security after Manuela told him Pilgrim and Sydney were plotting to kill him. He also cried a lot.

Soon he became fixated on Terry Holbrook, a 60-year-old former Ford model and Dallas Cowboys cheerleader. Manuela claimed Holbrook had received some $7 million from Sumner since meeting him in 2010. According to Keryn, Holbrook’s visits were arranged by nurse Jeremy Jagiello, who was secretly loyal to Shari and who controlled Sumner through access to the ex-model. Manuela was wary of Holbrook. According to Sumner’s lawyers, she had his doctor tell him that he was only allowed to have sex once a week. When he insisted on seeing Holbrook anyway, Manuela made up excuses why she could not come. More important, Manuela wanted to keep Sydney away. When Sydney’s lawyer asked Bishop to hand-deliver a letter to Sumner in which she apologized for her infidelity and professed her love, Manuela intercepted it. Meanwhile, Jagiello was eavesdropping in the house and reporting back to Shari’s son Tyler. According to Manuela’s complaint, Jagiello secretly recorded meetings between Sumner, Manuela, Bishop and the geriatric psychiatrist assessing competency and sent the information to Shari. On Sept. 18, Jagiello texted Tyler about their plans to oust Manuela: “Seal team commence operation freedom today.”

Exactly how Manuela came to be ejected from Redstone’s mansion in October 2015 is lost in a fog of accusations and counteraccusations, but a few things are clear. The first is that Sumner did not handle the breakup with Sydney well. He cried all the time and was more fragile and vulnerable than at any time in his long life. The second is that Manuela was not beloved by the household staff. After Sydney’s departure she unleashed what staff called a “reign of terror” against them. The third is that this terror extended into her wanting to keep rivals out of the house, whether they were Sydney or any of the women Sumner casually paid for sex. According to Manuela’s legal filings, in the days following Viacom CEO Philippe Dauman’s early October visit a group of household staff and nurses loyal to Shari went to Sumner to stage an intervention against Manuela. One showed him an earlier will that had him leaving her $15 million, not $50 million. According to Sumner’s legal filings, the mutiny was about love, not money — Manuela’s lying about Holbrook and intercepting Sydney’s apology.

Manuela woke up on the morning of Oct. 12 worried about Sumner’s health. He had seemed particularly out of sorts at the previous evening’s movie night. She told the nurses his doctor should examine him and then went out to run errands. When she got back, everything had changed. “Mr. Redstone doesn’t want you here,” said one nurse. Manuela went up to Sumner, who was staring vacantly. Bishop, the estate lawyer, demanded that Manuela leave the house so she could talk to him alone. “Do you want me to leave?” Manuela asked Sumner. “Are you mad at me?” In Manuela’s telling, he said nothing. In the telling of Sumner’s lawyers, he said, “Yes.” She asked again and Sumner grunted and began to bawl. She asked Jagiello what Sumner said and he replied that Sumner wanted her to leave. Bishop told Manuela she could come back later to collect her things.

On Oct. 16, 2015, Manuela was removed from her role as Sumner’s health-care proxy and erased from his will, paving the way for Shari and her children to re-enter Sumner’s life. Dauman was made the health-care proxy. The house was stripped of photos of Manuela and her family. And, according to Manuela, household staff were asked to sign loyalty oaths promising not to speak to Sumner about Manuela or communicate with her ever again.

Keach Hagey covers the media business for The Wall Street JournalAdapted from The King of Content: Sumner Redstone’s Battle for Viacom, CBS, and Everlasting Control of His Media Empire. © 2018 by Keach Hagey. Reprinted by permission of HarperBusiness.

This excerpt also appears in the July 11 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.