EPISODE 7
“I Want My $45 Million Back”
Holland’s million-dollar lawsuit against Naylor and Martinez had languished since she filed it the previous August. It had been ignored by the press, perhaps because Holland and Naylor were relative unknowns. But on June 25 the case burst into the headlines: Naylor filed court papers that not only denied stealing Holland’s laptop but also contained the far more explosive counterclaim that “Holland has effectively taken over Redstone’s life and does not allow anyone independent access to him.” With the link to Sumner, the story was suddenly newsworthy.
The lawsuit instantly became fodder for tabloid speculation and gossip that spread far beyond the confines of Hollywood. In New York, Vanity Fair editor Graydon Carter smelled a good story—an aging Hollywood billionaire with two live-in companions was a delectable mix of serious business and tabloid sex, the perfect recipe for a Vanity Fair feature. Carter asked the investigative business journalist William Cohan to look into it.
Naylor’s counterclaim had also triggered the Hollywood Reporter article that captured the reality-TV star George Pilgrim’s attention and prompted his string of Facebook messages to Holland—“I think your hot”—culminating in their passionate kiss at the Peninsula Hotel and Holland’s promise that she’d “take care” of him.
Notwithstanding her psychic’s prediction that she’d meet someone like Pilgrim, Holland surely knew only too well the perils of infidelity. She’d wielded the charge against the flight attendant Malia Andelin and had witnessed Sumner’s explosive reaction. Patti Stanger had warned her explicitly about cheating on Sumner, and even beyond that, Holland had reason to believe she was under surveillance by Jim Elroy, Shari’s private detective.
Nonetheless, the day after their first encounter, Pilgrim and Holland met at another entertainment industry watering hole, the Polo Lounge at the Beverly Hills Hotel.
Nestled in a curved, velvet-upholstered booth, they couldn’t keep their hands off each other. Holland suggested they get a room at the hotel so they could have sex, but Pilgrim declined. That only seemed to heighten his allure. Afterward Holland pelted him with suggestive texts and emails. When he told her he had to visit his mother in the New Age spiritual mecca of Sedona, Arizona, she proposed she meet him there.
Holland arrived by private jet and looked askance when Pilgrim picked her up in the aging Ford LTD he’d inherited from his grandmother. They went for lunch at the secluded Enchantment Resort, nestled in the red rocks of Boynton Canyon, then booked a room there.
Pilgrim felt “a lot of pressure,” he recalled, but “we made love,” and “it was beautiful.”
Afterward Holland told Pilgrim she thought she had already fallen in love with him. She promised to give him everything he could possibly want. “I’m in charge of a lot of power and a lot of things Sumner Redstone relies on,” Holland told him.
Holland booked the ($1,500) room for two nights but couldn’t stay—she needed to get back to Sumner. She told Pilgrim she was protecting Sumner from his daughter, Shari, who “hated” her and was trying to eject her. She warned him that Shari had hired a private detective to investigate her.
At one point Pilgrim asked Holland if she and Sumner were romantically involved.
“Are you crazy?” she responded. “He’s ninety years old.”
Closely allied though she and Herzer were, Holland made it clear to Pilgrim that she didn’t trust Herzer with the potentially explosive information about their love affair. Holland described Herzer as very aggressive about getting what she wanted, prompting Pilgrim to nickname her “Pitbull.” From Pilgrim’s perspective, the two women were constantly jockeying for power within the mansion and picking petty fights, like the time Herzer angrily blamed Holland after Sumner’s chauffeur failed to pick up her daughter on time. At one point Holland texted Pilgrim: “I am afraid to use the phone because I heard pitbull just walk by my room to go downstairs.” To avoid being overheard, Holland often communicated with Pilgrim via text.
Pilgrim knew of her plans to inherit Sumner’s estate but worried that Sumner’s family might supplant her. “I really don’t trust [Sumner],” Pilgrim warned her.
“I agree too but [Sumner’s family] won’t be able to do much I will be there the whole time so will pitbull,” Holland texted.
“I definitely wouldn’t leave [Sumner] alone with any of [Sumner’s family] now!!!” Pilgrim wrote.
“No way!!”
“Fuck them,” Pilgrim added.
“Exactly.”
“They’re going to try to play the Jewish family card watch!!!”
“Totally!!!” Holland agreed.
“But we’re family grandpa.”
“We love u.”
“BS!!!”
“Exactly they love his money,” Holland asserted.
“Yes,” Pilgrim agreed. “And to get all of it.”
Holland made good on her promise to take care of Pilgrim. They went house shopping in Sedona, looking for something in the range of $1 million to $5 million. To establish her financial bona fides, Holland showed the real estate agent, who happened to be Pilgrim’s stepfather, a trust account in her name with a balance of over $50 million.
After admiring the expansive decks and sweeping views of the surrounding cliffs, they settled on a 6,500-square-foot, five-bedroom house with a pool and hot tub for which Holland paid $3.5 million.
Pilgrim moved in that fall. Holland paid for their membership in the Seven Canyons club, with its championship golf course, spa and fitness center, and “privileged” access to the nearby Enchantment Resort. She paid for his health insurance. She bought him a new Jeep Cherokee and an iPhone. She dressed him in Ralph Lauren. She sent him gift coupons to Whole Foods.
She also bought him thousands of dollars’ worth of healing crystals, including black tourmalines, said to enhance sexual potency in men, which she positioned under their bed. Holland boasted she had Sumner’s signature and other paperwork on file and could use it to get Pilgrim a book deal for Citizen Pilgrim with Viacom-owned Simon & Schuster.
Holland showered Pilgrim’s parents with gifts, too. On her first visit she gave his mother an expensive bracelet, which the older woman considered odd, given that Holland had just met Pilgrim.
When not paying in cash—sacks of hundred-dollar bills were arriving weekly at Sumner’s mansion—Holland and Herzer charged virtually everything to Visa and American Express credit cards paid for by Sumner. In 2014 alone, the year Holland met Pilgrim, she and Herzer ran up over $3.5 million in charges. Holland charged $752,737 that year to her interior designer, Tracie Butler. For her part, Herzer splurged on expensive clothes: $128,780 at Barney’s, $82,624 at Hermès, $54,212 at Miu Miu, and $34,147 at Chanel.
Holland made the hour-and-twenty-five-minute flight from the Van Nuys Airport by private jet whenever she could (at a round-trip cost of $7,900 per flight, receipts show), spending the day with Pilgrim and having sex but leaving in time to be home for dinner with Sumner—her “curfew,” as Pilgrim described it. (“I can barely leave the house,” she complained in one text.) Sometimes she sent the private jet to pick Pilgrim up and meet her in Los Angeles. But Holland promised to move in with him in Arizona as soon as Sumner died—presumably soon.
On days Holland couldn’t travel she often sent him sexually provocative videos of herself in the mansion along with explicit text messages. Pilgrim saved them all.
“Need my cock sucked,” he wrote.
“I love you.”
“And I would love to do that soon.”
When she was away, Sumner called Holland constantly. She’d often put him on speaker, and Pilgrim heard him asking where she was and when she’d be back. Moments later he’d call again with the same questions. “Where is she? Somebody’s sick and Manuela’s not here and the dogs are running around. This was what her life was like,” Pilgrim recalled.
Much of what Pilgrim heard from Sumner was incomprehensible mumbling. But suddenly he’d articulate several relatively clear and coherent sentences.
Sumner’s constant calls got on Pilgrim’s nerves. At one point he suggested he meet Sumner, thinking it would allay the old man’s worries if he met and liked Holland’s new boyfriend. Holland firmly rebuffed the idea, saying Sumner was “old-fashioned” and wouldn’t understand. Pilgrim didn’t get it. Why would Sumner care? “What do you mean if you’re his fucking nurse?” he asked her.
The two fought often over Sumner’s constant demands, but Holland assured him it would all be worth it.
Pilgrim grudgingly agreed, but he pressed Holland to make sure her financial agreements with Sumner were “iron clad.”
“We need to be a family healthy working and having fun, this old man is draining u!!! He better come through,” he texted her.
“I agree.”
“U need now iron clad guarantee. No lip service. Cover us.” Pilgrim added, “You’re dropdead gorgeous beautiful woman, the situation [with Sumner] is temporary just cover all bases get everything ironclad. . . .”
“It is iron clad but can be changed while he is alive and of course hard to challenge,” she responded.
Sumner’s health continued to deteriorate that summer. In late June Holland and Herzer insisted that Sumner accompany them to New York over the objections of his nurses. “Sydney and Manuela nagged, cajoled, and pressured Mr. Redstone until he finally agreed to go,” Jagiello reported. The trip “took a real toll on Mr. Redstone. He was physically much weaker.”
One of his nurses, Joseph Octaviano, grew increasingly concerned about the care Sumner was receiving from Holland and Herzer. Sumner was frequently dehydrated, but Holland didn’t answer Octaviano’s text messages alerting her to the problem. He felt they were careless about Sumner’s feeding, cutting food into pieces too large for him to swallow comfortably. In August Octaviano had to perform the Heimlich maneuver after food blocked Sumner’s windpipe and he turned blue. Holland and Herzer “ran from the room,” Octaviano reported.
Pilgrim was also a witness to Holland’s often-dismissive treatment of Sumner, listening in when she’d put Pilgrim on speakerphone while she tended to Sumner. “I’m not your fucking nurse,” he heard her say on one call, and she told Pilgrim she was annoyed that Sumner had urinated in bed. Another time, he heard her say, “Why are you slobbering all over yourself?”
In early September Herzer was feeding Sumner fried rice and seemed oblivious that he was struggling to swallow and breathe. Octaviano and another nurse intervened and administered oxygen, which succeeded in reviving him.
Two days later Holland was with Sumner when he started choking and gasping. She called Pilgrim and put her phone on speaker so he could hear Sumner’s plight. From the strangled sounds he heard, he couldn’t tell whether Sumner was having a heart attack or a stroke or just choking. But it sounded serious. He overheard Holland say she was going to call 911 and Sumner repeatedly shouted “no.”
“Call 911 immediately!” Pilgrim yelled.
Sumner was rushed to Cedars-Sinai Medical Center and spent the night in intensive care, at which point his family was summoned. He was diagnosed with aspiration pneumonia, an infection often caused by inhaling food into the lungs.
Holland seemed more concerned about what to wear at the hospital than about Sumner’s condition. She sent Pilgrim a video of herself in what she called her “Star Wars” bathroom. “This is what I’m wearing today,” she says on camera. She pans over her diaphanous top and tight jeans while saying, “Gotta go to the hospital today.” She dons oversize sunglasses. “This is my casual chic outfit, with my big sunglasses so I don’t have to talk to people.” She takes off the sunglasses and shakes her dark hair. “Sending you a big kiss,” she mouths and then blows him a kiss. “Love you.”
Sumner was transferred to a private room that morning, and his nurse Giovanni Paz came to help with his care. As he was helping move Sumner from his bed to a reclining chair, Paz heard Sumner tell Holland, “I want my $45 million back.”
Holland did her best to change the subject, but Sumner persisted.
“I will give you your money back, but let’s not talk about this now, let’s talk about this another time,” Holland replied, according to Paz. But Sumner kept insisting that he wanted his money back.
“Your family is coming, please don’t do this to me,” Holland pleaded. Even as she spoke, Brandon was on his way to the hospital and Shari was flying in from Boston.
Holland spoke to someone on her cell phone—Paz assumed it was Herzer—then turned back to Paz and another nurse. “We have to put him to sleep,” she said. “You have to help me with this.”
Holland and the other nurse left the room, leaving Paz with Sumner. Five or ten minutes later a hospital nurse arrived and gave Sumner some medication. He was soon asleep, or close to it.
Brandon had called the hospital that morning to find out if it was a good time to visit, and was reassured that it was. His grandfather was awake and alert.
But when Brandon arrived and passed Paz in the hallway soon after the exchange with Holland, Paz tried unsuccessfully to get his attention. He followed Brandon into Sumner’s room, and Brandon was stunned by what he encountered—at first he thought his grandfather was dead.
But he was breathing shallowly. Brandon asked Paz why his grandfather’s eyes looked so “strange.” Brandon asked him to lower the shades so Sumner could sleep undisturbed.
Paz was deeply troubled by what he’d just witnessed. He strongly suspected the sleep-inducing medication was meant to prevent Sumner from raising the issue of the $45 million with Brandon, Shari, or anyone else.
When Paz left the hospital about a half hour later, he texted Brandon and asked him to call him when his visit was over, even though he knew that, if discovered, he could be fired for reaching out to Sumner’s grandson. When Brandon called, Paz told him what had happened. Brandon agreed with his assessment that Holland had asked for the sleep medication to keep Sumner from talking to his family. Brandon assured Paz he’d done the right thing and said he was going to call Shari.
“I think they might be trying to kill him,” he told his mother.
Shari arrived later that day. She was alone at her father’s bedside, holding his hand, when Octaviano came into the room. Like Paz, he mustered the courage to say something.
“Ma’am, could you lead your father’s care?” he asked.
Shari seemed startled and asked who he was.
He explained he was a nurse who spent six days a week with her father. He asked her to step outside the room and briefed her on what he described as Holland’s and Herzer’s “constant abuse” of her father.
Shari was upset. She gave him her email address and phone number and asked him to keep her informed.
Worried that he might be discovered and fired, Octaviano had his wife create a new email account solely for the purpose of communicating with Shari. “I am at your side and . . . will be willing to testify against Manuela and Sydney,” he wrote.
Sumner had evidently suffered some degree of brain damage—Herzer described it as a brain ischemia, a condition caused by insufficient blood flow to the brain. Symptoms include difficulty speaking and swallowing, slurred speech, and loss of coordination. In Sumner’s case, he could no longer chew and swallow food; a feeding tube had to be installed through his abdomen.
Sumner was discharged from Cedars-Sinai on September 9 at 3:00 p.m. and returned home to Beverly Park. Octaviano started filing detailed reports of the day’s events with Shari. In his first missive, he recounted a conversation between Holland and Sumner while he was watching television in the fish room:
“Will you still marry me?” Holland asked.
“Yes, tomorrow we will call a rabbi,” Sumner answered.
“Why don’t we wait for Friday?” Holland replied. “I will invite my lawyer and Manuela is here.”
But Holland could hardly marry Sumner and stay engaged to Pilgrim. By Friday talk of marriage had evaporated. So had talk of returning the $45 million.
The perils of communicating with Sumner’s family soon became apparent. Once Sumner was home, Holland told Paz he should have no further contact with him, leaving Paz little to do. “Don’t touch him,” she ordered when he tried to assist another nurse.
Two days later, a lawyer told Paz he was being “let go” but offered him a check for a month’s salary if he signed a declaration. When Paz declined, saying he wanted his own lawyer to read it first, Holland came over and stood “inches away from me,” he recalled, and said: “Get out of my house.”
Sumner was now more dependent than ever on Holland, Herzer, and the nursing staff at the mansion. In addition to the feeding tube, he needed a catheter. He couldn’t walk unassisted. His speech was seriously impaired, all but unintelligible to those unused to interpreting him. Still, he managed to communicate, usually through his nurse Jagiello. Jagiello spent so much time with Sumner and became so skilled an interpreter that his nickname was “the Sumner whisperer.”
Sumner still watched sports on television. No one had been a more avid sports fan than him, especially when it came to his favorite hometown teams, the Patriots and the Red Sox (at least when they were winning), but now he rarely seemed to know what team was playing. Nor did he seem aware that most of the games he watched were prerecorded rather than live. He had ongoing, substantial bets on the outcomes with his nephew Steven Sweetwood, the broker who had set him up with his second wife, Paula. Sumner always won the bet, because Sweetwood already knew the outcome and arranged for Sumner to bet on the winning team.
Shari was planning a follow-up visit for September 15, and the day before, she spoke to her father on the phone. Despite her earlier vow to take legal action against Holland and Herzer, she now had second thoughts. As she wrote in an email to her three children: “We would not win a lawsuit to get rid of S and M,” again referring to Sydney and Manuela. “And that would not necessarily be the right thing to do.” After all, Sumner himself had made the decisions he did. “I just called to tell him that I love him and I would be there tomorrow, and all he kept saying was leave Sydney and Manuela alone. He said it one hundred times. He was not interested in the fact that I loved him or that Tyler and I were coming out.
“We all have amazing lives surrounded by people we love and who love us,” Shari continued. “This should not be taking over our lives and destroying our days . . . and nights!!!! Agonizing everyday accomplishes nothing. I do not deny that this is an awful situation, but it is an awful situation that he created and that we cannot undo. This is a very hard decision but after much agony and many tears, I really believe that we cannot let this destroy our lives any longer. . . . Rosh Hashana is next week and I think we all need to commit to a new beginning.”
The next day Shari and Tyler arrived at Sumner’s mansion at about noon. Fortunately for them, Holland and Herzer were both out shopping. Mother and son’s main goal was to reassure their father and grandfather they loved him and to counter Holland’s and Herzer’s claims to the contrary. But a staff member quickly alerted Holland that Shari and Tyler were at the house. They’d been there about twenty minutes and thought they were having a good conversation, given the constraints of Sumner’s speech, when Holland phoned and was put through to Sumner.
Shari and Tyler could hear Holland’s end of the conversation.
“Are they upsetting you?” she asked. “Are they making you cry? You have got to get them out.”
Sumner turned to his daughter and grandson. “You have to go,” he said, and then started crying. Shari knelt by his chair and held his hand.
“Do you really want us to leave?”
Sumner nodded yes. “I love you so much,” he managed to articulate. “But you have to go.”
Shari, too, was now in tears. She thought it likely this was the last time she’d see her father alive.
“At least you heard what you needed to hear,” Tyler said as they walked out.
After witnessing the exchange, Octaviano sent Shari an email: “Today’s incident is so unforgiving. I’m so sorry. It is not the end of the rope ma’am Shari. I am at your side and 99% of the staff will be willing to testify against [the] brutality of Manuela and Sydney to your Dad. From the day I worked there, I witnessed verbal abuse almost every day. Nagging, threatening and back stabbing to win your Dad’s sympathy and a lot of document signing. One time Manuela told your Dad that none of his family loves him except them. Yesterday, Sydney ask your Dad if he still loves her and he replied, ‘NO, I’m so tired, leave me alone, I want to die.’ ”
Octaviano continued that Sumner sometimes cried out for help, but there was little or nothing the staff could do: “Every move in that house is controlled by Manuela and Sydney.”
Octaviano’s email concluded: “Your Dad always looks so sad and helpless. My heart really falls apart every time these happen.”
This was too painful for Shari to read. She thanked Octaviano for the information but asked him to send all future correspondence to Tyler.
Shari felt there was nothing more she could do. Maybe it was time to follow her brother out of the family business and sell her stake in National Amusements. She could invest the proceeds in Advancit Capital, her venture capital enterprise, and continue her philanthropic efforts, free from the drama of her father and his consorts. She and Bishop started negotiating for her father to buy out her stake.