The Downfall of Sumner Redstone

Jarosława Radowski
10 min readFeb 27, 2021

--

Media mogul families tend to be incredibly dysfunctional. The most famous are probably the Murdochs and Fox News (a subsidiary of Newscorp) but this post orients around the Redstone family.

America’s five biggest television networks are NBC (Comcast), CBS (ViacomCBS), ABC (Disney), Fox (Newscorp), and The CW (50% ViacomCBS / 50% WarnerMedia).

Of these five companies, you can arguably claim three of them are family owned (Comcast, ViacomCBS, and Newscorp). ViacomCBS is currently under the control of the Redstone family.

Who is Sumner Redstone?

Sumner Redstone

Sumner Redstone was a self-made businessman: he took his father’s local theater chain and turned it into a heavyweight media conglomerate, owning Viacom, Paramount Pictures, and CBS which also meant they owned MTV, Nickelodeon, Showtime, and Comedy Central.

Sumner Redstone was famous for his term “Content is king” meaning he believed the success of his business depended on the content his companies produced rather than how they were distributed and marketed.

In reality, Sumner Redstone was incredibly lucky. As Columbia Business School professor Bruce Greenwald puts it: “He bought companies, put them together, pulled them apart, with no particular economic logic.”¹

He was also an asshole. When an executive Tom Freston questioned the bidding war for Paramount, Sumner bellowed “No one shits in my mouth!” into his face.² In 2006, he ordered a flight crew out of their homes at Christmas so he could watch the New England Patriots on the corporate plane’s satellite dish when the local TV would only play the NY Giants. One Hollywood producer witnessed the 80-year-old throw an overdone steak at a waiter during a family holiday dinner: when she asked why Sumner did this, he responded that “I don’t care” and that “I’m going to hell anyway.”²

According to his ex-wife Phyllis, she was “verbally and physically and financially abused by him every day of her life.”¹ Together they would go on to file divorce against one another at least four times.

Maybe it was destiny due to a turbulent childhood. “My family, basically, it was a dysfunctional family. It really was. And still is,” said Sumner’s younger brother Edward, who lambasted his parents as tyrannical and mean.² Sumner didn’t even attend his brother’s funeral. The Redstone family has been filing lawsuits against each other for control of the company, and the legal battles has transcended down four generations.

Denial of Aging

Sumner Redstone frequently boasted of his immortality ever since he survived a hotel fire by hanging out a window (followed by 30 hours of surgery for his burns). Inconveniently, whenever Sumner shares this story, he leaves out the detail that he was frolicking with his mistress Delsa Winer when this happened (she escaped with less severe burns).

Regardless, Sumner Redstone failed to conquer old age. Aspiration pneumonia severely crippled him. He struggled to walk, swallow food, and speak clearly, relegating him to an iPad to communicate using three buttons (yes, no, fuck you). By 2014, witnesses reported Redstone drooling and dozing during meetings.

Further salacious details would emerge when Sumner’s ex-girlfriends would sue him (and his family): Female escorts visiting his mansion, random crying spells, and demands to eat steak despite being on a feeding tube.

If you’re wondering why ViacomCBS’s stock has been slowly tanking since the late half of the 2010s, it’s because Sumner Redstone still commanded 80% of the voting shares.

The Question of Succession

“[Sumner] treated his two children, Brent and Shari, the way he treated the executives who ran the companies he gobbled up: golden until they challenged him, disposable when they did” -NY magazine.¹

Shari was Sumner’s favorite, and when her father determined Brent was too “weak-willed for the job,”¹ he recruited Shari’s husband Ira, and then Shari herself after she divorced (Ira left the company afterwards).

When Phyllis decided to file for divorce the final time, Shari made her mark by agreeing to give her voting control over to her father (who was worried a divorce settlement would make him lose control of the company). Brent, who refused, was later kicked off the Viacom board. Brent later sued his father in retaliation, and won a $240 million settlement. As a result of this lawsuit, Brett and Sumner stopped talking to each other for decades.

In 2004, Shari was rumored to be Sumner’s successor, and Sumner even encouraged it. Yet conflict continued to arise between the two over Sumner’s increasingly terrible business decisions. This included investments into Midway Games and The Electric Barbarellas. Sumner actually called the journalist to find out which company insider leaked his meddling in The Electric Barbarellas, clarifying, “We’re not going to kill him. We just want to talk to him.”³

Over time, Sumner became increasingly agitated with Shari. “It must be remembered that I gave to my children their stock” he would fax a reporter, and yet several months later he would say that he would like his legacy to be “known as a loving and supportive father and grandfather.”¹ Witnesses say Sumner called his daughter a cunt multiple times, even during a board meeting once.

Shari became so disgruntled with Sumner that she threatened to sue for mismanagement and mistreatment. By 2011, she started a venture capital firm with her son-in-law and basically left Sumner alone.

Sumner’s Girls

Sumner then married a schoolteacher half his age and then moved into Beverley Hills where he would often swim in the backyard pool naked. The couple also bragged how much sex they had to their friends. When they divorced, Sumner soon had a series of women who he’d bring to red carpet events and soon afterwards would end up wealthy.

These included Rohini Singh, a “party girl” (as featured on LA magazine) who bought a $2 million house; Malia Andelin, a flight attendant from CBS’s corporate jet bought a $2.65 million home who established a nonprofit (Kidnected World) which paid salaries to her family; and Heather Naylor, MTV assistant who got her reality TV show (The Electric Barbarellas) and a $1.24 million home.

Thinking Grumpy (as Sumner’s grandchildren called him) needed a new kind of female companion, Brandon Korff (Shari’s son) signed grandpa up for Patti Stanger’s Bravo’s Millionaire Matchmaker program. It was there where he met Sydney Holland, a recovering alcoholic divorcee who was paid $164K by Bruce Parker (her last sugar daddy)’s family to get her to vacate his house after Parker died from a heart attack due to having sex with Holland on cocaine. The autopsy report attributed the death to “cocaine toxicity.”

“She was the perfect fit for him… They’re both Geminis. And she loved older men.”

-Patti Stanger³

The lovely couple soon made a new addition: Manuela Herzer. Born in Argentina, previously married to a Lebanese-American with Nigerian business interests, Herzer became infamous with Viacom executives for demanding VIP treatment. Such was her entitlement that Justin Timberlake complained to executives about her.

From left to right: Manuela Herzer, Sumner Redstone, Sydney Holland

I will refer to these two henceforth as “The Women” as Shari’s confidants refer to them as. Through lawsuits and blackmailing, these two worked together to block off Sumner’s other mistresses (at least, those out of their influence), his friends, and his family.

“[Sumner’s house] was a scene of death threats, accusations of theft, demands for sex, the mysterious shredding of documents, drugging, screaming, scheming, and other scenes of infighting too outré for a Danielle Steel novel.”

-The New Yorker⁴

The Women would drain Sumner’s bank accounts and even amended his will to leave them both with $45 million each. Longtime executives at Viacom (most infamously Philippe Dauman) actually tolerated this behavior because they wanted Shari out. Their complicity encouraged Sumner, who at the age of 91 refused to discuss succession with reporters because “he’s not going to die.”³

The Women worked especially hard to block Sumner from seeing his family, even preventing Shari from entering the Beverly Park gate. They even prevented calls from the Redstones to reach Sumner, although they did foster a relationship with Keryn Redstone — the adult daughter of Brent Redstone.

Shari hired a retired FBI agent as a private investigator to dig up Holland and Herzer’s pasts, whereas the women would constantly fire nurses for reporting to Shari’s other son Tyler. In the coming legal battles, the nurses would report Sumner was being emotionally abused by The Women, who would tell him that his grandchildren hated him, that he would die alone, and if he really loved them as much as they did for him.

The Women’s Downfall

Seeking to cement their role in Sumner’s family (and his will), The Women decided to go public with their ménage à trois. They hired a PR firm and cooperated with Vanity Fair, directly against the advice of Viacom executives and legal counsel.

The publicity shocked one dude named George Pilgrim, because up to that point he thought he was in a relationship with Holland. They had bonded with each other on Facebook, where Pilgrim sent unsolicited messages to her commending her takedown of Heather Naylor (who was part of the mistress knife-fight I mentioned above).

At that point, Pilgrim was told by Holland that Holland’s relationship with Sumner was not romantic, as she characterized their relationship as a student and mentor; she was just in charge of his health (and sexual escapades… According to Sumner’s personal chauffeur, Holland also paid hundreds of thousands of dollars to 7 women to visit Sumner 2 or 3 times a week for reasons he did not know but was certain “they weren’t coming over to bake cookies.”)³

The article suggested otherwise, and Pilgrim threatened to talk about their relationship. Legal action ensued, but before a potential $10 million settlement was finalized, Pilgrim foolishly introduced himself to Herzer when he recognized her at a diner.

Herzer, who was unaware of Pilgrim’s existence, got spooked. She and her lawyers convinced Holland to confess to Sumner, who then had her kicked off his property. Even more paranoid of her grasp on the Redstone legacy, Herzer consolidated her power right away by taking all of Holland’s share, inviting Keryn to move in with her, and restricting Sumner’s sexual activities (she had a doctor tell Sumner he was allowed to have sex once a month).

“A male nurse was in the room with Sumner and me, directing me and telling me what sex acts I should perform. At the conclusion of my time with Sumner, the male nurse would sometimes tell Sumner that he had ejaculated, when in fact Sumner had not. Nevertheless, Sumner appeared to believe him, not aware of the truth.”

-Heidi MacKinney⁵

Sumner’s household staff members did not like Herzer at all. One important nurse, Jeremy Jagiello (nicknamed “Sumner Whisperer” by the staff for his talent of deciphering Sumner’s grunts), conspired against her and kept in contact with Tyler. One day Herzer returned from an errand to be confronted by staff members, an armed security guard, and Redstone’s estate lawyer (Leah Bishop). They told Herzer that Sumner no longer wanted to see her, and after a brief standoff, Herzer agreed to leave. Keryn Redstone was also prevented from seeing Grumpy; the last she saw Sumner was during a Deadpool screening in which “he cried at the opening credits.”⁶

All of this cleared way for Shari Redstone and her children to finally talk to her father.

The Aftermath

Herzer responded to her “coup” (as her lawyer put it) by filing lawsuits claiming Sumner had become conveniently incapacitated. Sumner, according to Herzer’s lawyer, was mentally competent through September 2015 (when Holland was evicted and Herzer was named healthcare agent) until six weeks later, when he ordered Herzer out of the house.

Was it true? Sumner did change course on many issues during his daughter’s visits, often to Shari’s advantage. Yet this was witnessed by two nurses (one of them Jagiello) and his probate lawyer who insist Sumner was competent to execute his own wishes.

Yet they also worked really hard to prevent Sumner from being examined by third party geriatric psychologists. When Herzer’s lawyer finally won the Judge’s approval, Dr. Stephen Read’s report on Sumner was less flattering.

“Suffice to say… those details are difficult to read in describing how this man is hanging on to life.”

-Judge Cowan⁵

Six days later after the medical exam, after years of bad press and attention, Sumner Redstone resigned as executive Chairman.

The keys to the throne were originally meant to be handed to Philippe Dauman, an executive who was a constant hindrance to Shari Redstone’s business ambitions. With Sumner’s moment of clarity (under Shari’s supervision), he removed Dauman from the family trust by March 2016. Like Herzer, Dauman would later go on to sue claiming Sumner was mentally incapacitated and manipulated by his daughter. But at the moment, it was clear he was not going to earn the crown.

Vice chair Shari Redstone waived her rights of succession so Les Moonves could step in. These former friends would later turn to bitter rivals, fighting over control of CBS. Luckily for Shari, Moonves would soon be overthrown due to sexual harassment accusations, allowing her to become Chairwoman of the board of ViacomCBS.

Meanwhile, Herzer lost her suit and then filed a RICO suit, claiming Sumner had been manipulated by his daughter. Holland tried to ease her way in more quietly, by writing letters of apology to Sumner and voicing her disgust of Herzer’s lawsuits through her attorney. Soon after, in October 2016, Sumner filed an elder abuse lawsuit against Herzer and Holland.

After a few more bumps — details of the settlement was leaked out to the press, which imploded a deal at one point — the dust settled with settlements being shelled (late Jan 2019) out and agreements being made. The Women kept most of their previous gifts and properties, and Shari remained the healthcare proxy. Dauman also snagged a $58 million severance pay in return for dropping his lawsuit.

--

--

Jarosława Radowski

I attended one of Colorado's best public colleges (online only) and got really good grades.