Although Holland was still officially engaged to Sumner and had again proposed marrying him, she never mentioned this to Pilgrim. In the fall of 2014, just after Sumner got out of the hospital, Pilgrim texted Holland emojis of a family and then a bride and wedding band. He called her and proposed. She didn’t answer for fear of being overheard by Herzer.
“Is that yes?” he texted.
“Yes, yes,” Holland answered.
“Omg. I’m so happy,” Pilgrim replied.
“Me too,” Holland typed, followed by a long string of heart emojis.
Pilgrim impulsively suggested they drop everything and “run away.”
“Let’s get married and run away and hide in Sedona.”
“Our World,” Holland answered.
“And we travel all over run away,” Pilgrim wrote in successive texts.
“Yes please.”
“Perfect to me.”
“I’ll save u let’s run away,” Pilgrim suggested again.
“Done.”
“There’s a whole Universe.”
“Fuck those losers.”
“Agreed,” Holland wrote.
“Waiting for a man to die!!! Fuck that we can be explorers travel the world Indiana jones stuff,” Pilgrim elaborated.
“I know,” Holland responded.
“It sucks for both of us I am sorry.”
“Sorry.”
In their text messages, Holland and Pilgrim began referring to each other as “husband” and “wife.”
“God I need you inside of me. I miss your smell and taste,” Holland texted him.
“Love u more my wife.”
“Love you more Husband xoxoxoxoxo.”
“I’m your soulmate.”
“Husband.”
“Your my soulmate . . .”
“I hope we die at the same time.”
“Wouldn’t want to be without you.”
On October 8 Holland brought her parents to Sedona to meet Pilgrim and his family. The future in-laws had lunch together at the Enchantment Resort, which seemed to be going well until Holland’s mother told Pilgrim’s mother that she should consider losing weight. Afterward Holland and Pilgrim had sex while her parents went shopping for crystals.
As soon as Holland accepted his marriage proposal, Holland and Pilgrim started planning for a baby of their own, with Holland again using artificial insemination, an egg donor, and a surrogate. Pilgrim signed a formal sperm donor agreement relinquishing any paternity rights. They went to the same fertility doctor in Beverly Hills whom Holland had used to conceive Alexandra, where Pilgrim complained to the doctor about having to masturbate into a cup while people walked by in the adjacent hallway. The doctor said it wasn’t necessary—he could “stick a needle” into Pilgrim’s testicles, just as he’d done for “the old man.” But at that point Holland signaled the doctor to say no more.
Pilgrim dutifully used the cup, even though his mind was racing: Who did he mean by “old man”? Had Sumner and Holland also planned to have children? Who was Alexandra’s father? Once they were in Holland’s chauffeur-driven car outside, Pilgrim demanded an explanation. “If we’re going to have kids together, I have to know the truth,” he said. “What the fuck is going on?”
Holland looked at him, and Pilgrim thought she was finally going to give him an honest answer. But then the driver asked for directions, and the spell was broken. “Just let it go,” Holland said. “We’ll talk about it later.”
On October 28, Pilgrim and Holland exchanged another round of text messages:
“I gave you my blood today . . . my sperm,” Pilgrim wrote.
“I know. Thanks,” Holland replied. “I give you my heart and soul. . . . Thanks for doing all of this I know it is so different to do things this way.”
“It’s my honor my wife. Anything for u. Anything!!”
“Thank you Husband.”
“Love u my wife.”
“Love you my Husband.”
“We are so lucky to have each other,” Pilgrim reminded her.
“We sure are,” she answered. “Very. I waited my whole life for you.”
Holland’s devotion didn’t extend to spending Christmas Day with Pilgrim in Sedona. Instead, she and Herzer and their children gathered at Sumner’s mansion. While they celebrated in the living room, Sumner languished in another room, alone except for Octaviano and other nurses. At about 3:00 p.m., Sumner asked to see the Christmas tree. When Octaviano wheeled him into the living room, Herzer seemed surprised but exclaimed, “Sumner, this is your family.”
Sumner “immediately began sobbing,” Octaviano recalled.
After nearly a year’s effort, by November Sumner and Shari had reached the framework of an agreement for him to buy out his daughter’s 20 percent stake in National Amusements. Shari would receive $1 billion in cash and stock, tax-free. In return, she would no longer succeed Sumner as chair of either CBS or Viacom.
Shari was ready to sign.
But Holland and Herzer, apparently, were not ready for Sumner to sign.
Octaviano’s daily missives to Tyler described a stream of visits from Andelman, Bishop, and other lawyers, meetings that often left Sumner in tears. In one meeting with Bishop, Octaviano recalled hearing Sumner cry out, “No, no, no,” and then start to sob.
As Tyler told Andelman in an earlier email, “Manuela and Sydney dictate to SMR everything he MUST say in conversation with Leah and verbally abuse him if he deviates. I’m told they verbally abuse him, threaten him and nag him on a daily basis.”
Suddenly, Bishop injected a new condition into the buyout: Sumner insisted that Shari had to agree not to contest any of the enormous gifts he’d made (and was continuing to make) to Holland and Herzer.
Octaviano was on duty January 8 and reported that Sumner was “exceedingly groggy and disoriented that morning.” In Octaviano’s account, a befuddled Sumner asked his nurse Jagiello, “What’s happening, where am I?”
Bishop arrived at 11:30 a.m. and spent twenty minutes with Sumner, with Holland present. Octaviano heard Sumner cry throughout the meeting and then off and on throughout the day. Holland instructed Octaviano to block all calls to Sumner and specifically banned any from Shari or Kimberlee. When Kimberlee called, she was rebuffed.
Later that afternoon, Octaviano overheard a conversation between Sumner and Holland, with Herzer connected by speakerphone. Holland told Sumner that “his family did not love him” and “never even called,” Octaviano reported. Holland said Shari was suing her, which further upset Sumner (and wasn’t true). Herzer added that Shari was “mentally unstable.”
In this instance Sumner pushed back: “I know Shari cares,” Sumner insisted; Shari and her children were his family.
But Holland and Herzer prevailed. A letter sent that day to Shari and his grandchildren, signed by Sumner, read: “I want to be able to spend the rest of my life, however long that is, knowing that Sydney and Manuela will not be faced with litigation from my family at a time when they are grieving my passing.”
The letter continued. “I want to enjoy the rest of my time on earth with peace of mind. If you decline to sign a release agreement, I will be compelled, albeit with deep regret, to direct Sydney and Manuela not to allow you, Phyllis or your children to attend the funeral or in any way be involved in the burial arrangements.”
Shari was stunned. That was asking too much. She refused to sign the release. Negotiations to sell her stake in National Amusements came to an abrupt halt.
The next day Octaviano reported that Sumner was “very unstable” and “cries most of the time.”
That evening Sumner’s executive assistant in New York, Gloria Mazzeo, dispatched an email from Sumner to Brandon, Kimberlee, and Tyler: “Your mother has no respect for me. The letter I wrote to all three of you and your mother are my wishes, and they apply to all three of you, including you, Tyler. I want there to be no misunderstanding.”
Tyler couldn’t believe this really reflected his grandfather’s wishes, given Octaviano’s report of what happened that day: “Sydney wrote a note and made SMR [Sumner] approved it and Jeremy read it to Gloria and that Gloria needed to send it to Ma’am Shari, Brandon, Kim and you. I did not hear the whole thing but what I catches was that, ‘your Mom has no respect on me.’ ”
This was obviously a description of the email Mazzeo had transmitted.
On January 12, 2015, Tyler wrote to Bishop:
Now that the spin-off negotiations between National Amusements and my mother have concluded, it is apparent that Sydney and Manuela are prepared to ban the family from attending my grandfather’s funeral unless we sign releases.
Please be advised that my grandfather expressed his explicit wishes recently that his family must not be prevented from attending his funeral. Additionally, Sydney and Manuela have now blocked my siblings’ and my own telephone calls to my grandfather and have effectively prevented us from speaking with him. Instead, they lie to my grandfather that we do not call him or love him.
For thirty years, my siblings and I have had a wonderful, loving, and caring relationship with my grandfather, and we continue to love him dearly. Both the January 8th letter and the January 10th email, however, make it abundantly clear that Sydney and Manuela will continue to drive a wedge into that relationship and to abuse my grandfather until we agree to immunize them for their past and continuing misconduct.
Because I am prevented from calling my grandfather directly, please relay to him how much I love and care for him, and how I welcome the opportunity to speak and visit with him soon.
Almost immediately Holland had a copy of Tyler’s letter. She came out to the patio where Sumner was sitting with Octaviano brandishing it. She ordered him and the other nurses into the kitchen, but Octaviano heard her angrily read parts of the letter aloud to Sumner and call Tyler a liar. She complained his family was “ruining her life.”
For her part, Bishop wrote Tyler that “this letter did not come from Sydney and Manuela. I prepared it at Sumner’s direction. I met with him and went over it multiple times to confirm it was exactly what he wanted and he signed it. My only goal here is to carry out Sumner’s wishes.”
That same day, January 12, one of the nurses put through a call to Sumner from his granddaughter Kimberlee. Octaviano reported that it made Sumner “very happy and he told Kim repeatedly that she and her family can come visit him anytime soon.”
Holland, predictably, was furious when she found out. Of the Redstone grandchildren, Kimberlee seemed to annoy Holland the most. In texts to Pilgrim she called her “such a little spy,” a “manipulator,” and “her mother’s daughter.”
Holland told Sumner that Kimberlee was a liar.
“I love Kim,” Sumner responded.
Her whole family were liars, Holland insisted.
“No, they are not!” Sumner argued.
This back-and-forth went on for an hour, punctuated by yelling and crying episodes.
Octaviano duly reported these events to Tyler, who had been willing to at least discuss the possibility of litigation releases with Holland and Herzer. But he was disturbed by their demands for control over the funeral, their threats to exclude family members, and now these latest attempts to turn Sumner against his family. When he again complained to Bishop, she responded, “Sydney and Manuela are not banning anyone from Sumner’s funeral. Sumner has given this direction.”
If Sumner (or Holland and Herzer) thought threatening to exclude his daughter from his funeral would be persuasive, they were mistaken. It seemed to have the opposite effect. Shari told her children she’d refuse to “sign releases against the whores who will be grieving his loss” and that “there is absolutely nothing more to be said . . . EVER!!!!”
The ongoing pattern of abuse was too much for Octaviano. On January 29 he and several other staff members lodged the first of two complaints against Holland and Herzer with Los Angeles County Adult Protective Services. They also filed a separate complaint against Bishop, whom Octaviano deemed complicit in the abusive conduct.
Sumner’s nurse Jagiello joined in the complaints. “From my personal observations during my frequent 12-hour shifts, I was firmly convinced that Sydney and Manuela were emotionally and financially abusing Mr. Redstone,” he stated. “I further believed, and still believe today, that both Sydney and Manuela extorted Mr. Redstone by leading him to believe that if he did not keep them financially satisfied he would die alone because they were the only people who loved him.”
Like Octaviano, Jagiello also lodged a complaint against Bishop: “Based on the interactions I observed her having with Sydney and Manuela, I was concerned that she might be advancing their agenda rather than the interests of her client, Mr. Redstone.”
Through all of this turmoil, Sumner was not just a controlling shareholder—he was also the executive chairman of two major publicly traded companies. His base pay was $1.75 million at CBS and $2 million at Viacom.
Even though Sumner named the directors by virtue of his controlling shares, they owed all shareholders a fiduciary duty of care. On January 28 the CBS compensation committee met to consider what CBS should pay Sumner for the prior year, 2014. The committee had clearly spelled out Sumner’s duties as executive chairman: serving as “a sounding-board/counselor to [the] CEO on issues of strategic importance,” ensuring that “strategic plans are up-to-date” and “being executed on,” providing “effective communications with the Board,” and assisting “the Board in maintaining best governance practices.”
At the CBS annual meeting in May 2014, Sumner had had to be carried into the room in a chair, and at subsequent board meetings he attended by phone and usually said nothing other than “Hello, everyone.”
Yet the minutes of the compensation committee’s meeting reflect no discussion of Sumner’s condition or whether he in fact performed any of his specified duties. The committee recommended, and the full CBS board approved, a $9 million bonus, bringing Sumner’s pay that year to $10.75 million.
At Viacom, Dauman was presumably well aware of Sumner’s mental and physical limitations from his frequent visits. Yet Viacom paid Sumner even more—over $13 million for fiscal year 2014.
A few days after Jagiello and Octaviano lodged their complaints, two investigators from Adult Protective Services showed up at the Beverly Park entrance gate seeking access to Sumner. The entrance guard called the house, and a staff member there promptly informed Holland, who was out. She ordered the staff not to admit the investigators and insisted they make an appointment for a later day.
Once they were back in Los Angeles, Holland and Herzer met with Sumner. He was “upset,” in Jagiello’s recollection.
“I’m in trouble,” Sumner said. “Sydney and Manuela got me in trouble.”
Minutes later Robert Shapiro, the celebrity lawyer best known for his defense of O. J. Simpson, showed up at the mansion, evidently retained by Holland or Herzer or both. Bishop arrived soon after and all of them met with Sumner to rehearse him for an encounter with the investigators, who arrived later that day. All were present for Sumner’s interview, such as it was, in which Herzer maintained that Sumner denied being abused or pressured. Jagiello reported that the investigators stayed only briefly and spoke to none of the nurses or anyone on the household staff—even though the multiple complaints had been lodged by nurses. Nor did they reach out to anyone in Sumner’s family.
That was the end of any investigation.
By now Herzer and Holland must have been aware, or at least suspicious, that someone on the household or nursing staff was leaking information, despite the strict confidentiality agreements they’d signed. Octaviano warned Tyler in April that they were out to “catch the person that gives you guys informations. CAREFUL is the name of the game this time.”
“Yes, careful is key!” Tyler responded. “I don’t tell anybody anything about you or Jeremy. Thanks for the update and the warning.”
Jagiello kept reporting the latest developments to Tyler. Though his effort to enlist Adult Protective Services had gone nowhere, he was more determined than ever. “These women and their fucking cronies are going down!” he texted Tyler on May 14. “Can’t stand them and who they are and what they do. I want to vomit!”