What a night for Sumner Redstone! February 1992, down at an executive retreat in Key West, Florida, where the tequila always flows. There he is, the media emperor himself, Mr Redstone – once derided by his rivals as “that peasant from Boston” – now holding court with his top guys at the Viva Zapata club. This young man of 68 is knocking back shots and roaring about the success of MTV, the hottest stud in his stable of television channels at Viacom.

“So listen to me, you turkeys!” he shouts at his team, who are lapping it up. “Only a short four-and-a-half years ago there were still some in the world who considered that MTV was a fad. MTV is now entrenched as part of the culture of America and fast becoming entrenched in the culture of the world.”

“Redstone for President! Redstone for President!” his execs chant, pouring more tequila. His tongue loosened, Redstone has an idea and collars Tom Freston, MTV’s CEO, and complains about all that rock and roll muck on the channel. Why does he never broadcast more real musicians like Tommy Dorsey? Now he could really play trombone. So could Benny Goodman with his clarinet! Hey, how about Tony Bennett?

He pushes him hard, Freston bows to pressure and broadcasts videos of Tony Bennett, the crooner old enough to be the grandfather of MTV fans, on his channel. Turns out, the Generation X slackers who watch MTV love him – they start buying his albums and breathe new life into his career. A classic Redstone move.

Well, at least that’s the way he tells it in his autobiography, 

. When the book came out in 2001, Redstone’s execs would have been too scared of him to loudly disagree. Now that he’s passed away, aged 97, who knows if the Redstone record will be corrected?

In Redstone’s world, you’re either a “winner” or a “patsy”. Winners like him got to control one of America’s biggest media firms – an empire which included MTV, Nickelodeon, VH1, CBS, Simon & Schuster, Paramount Pictures, Showtime and Comedy Central.

"You cannot “retreat and survive”, victory meant eating the other guy."

And nobody runs that amount of media real estate without gaining a fearsome reputation. Some highlights: in a moment of pure boardroom rage, he shouted so loudly at his lawyer that a tooth dislodged from his gums and flew over the carpet. One time mid-rant, he accidentally set a load of cigar wrapping on fire and flames billowed into the air, but he didn’t notice and his minions were too afraid to tell him. In his old age, after his speech started to go, he had an iPad with three audio recordings ready to keep conversation going: “yes”, “no”, and “f*ck you”.

, the HBO show about the awful children of a media billionaire fighting to become his heir, will note the similarities in the fictitious Roy family and Redstone’s story. Here was one of the last boardroom pirates of old corporate America; a terrifying bastard who smashed possessions against the wall and swallowed lawsuits like pistachios.

A Jewish boy from Boston (his father changed the family name to Redstone from Rothstein), he learned a valuable lesson getting his ass kicked by anti-Semitic Irish kids on the way to school: “life is rough”. You cannot “retreat and survive”, victory meant eating the other guy. He went up to Harvard before World War Two broke out where, with all the modesty of a future billionaire, he claimed to have memorised the German dictionary before an exam, learned Japanese better than “the average Japanese on the street”, and, upon becoming a codebreaker during the war, staying up three nights on the trot to get his work done. In the 1970s, his hotel room burned down and he suffered third-degree burns on 45 per cent of his body. He was in hospital for months, enduring painful skin grafts and rehabilitation. No lesson learned from coming through adversity though: “I have always been driven,” he wrote.

Sumner Redstone with Sydney Holland and Manuela Herzer


His father Michael, who sold linoleum out of a truck (and perhaps booze during Prohibition), got into the entertainment business in the 1930s, ultimately owning a restaurant, two nightclubs and two drive-in theatres. Sumner took over National Amusements in the 1950s and, by pursuing an aggressive strategy of litigating his way into the movie distribution business and then buying Viacom in a hostile takeover, he turned his old man’s company into an $80 billion giant.

“Content is king,” he liked to say. “If your competitor has an inferior theatre and the hot show, he is going to do better than you.” This mantra was his way of turning piles of money into mountains of money. After seeing an early screening of 

, he left the cinema, walked across the street to a gas station and used the pay phone to buy 25,000 shares in Twentieth Century Fox. When he was in a bidding war to buy Paramount Pictures in the 1990s, he was short by $600 million – so he organised a stock swap with Blockbuster. The enormous cash flow from the movie rental company, then at the height of its popularity, helped service the debt from taking on the studio for $8.2 billion. These, in the vernacular of the young guns of today’s Wall Street, are the moves of a size lord.

Redstone liked to joke that he would never retire, but eventually his age started to catch up with him. An encounter in the early 90s with Robert Maxwell, the news mogul and father of Ghislaine, would prove prophetic. One evening, Maxwell goaded him at dinner: “If I walked down the streets of Japan with a beautiful woman, all the media in the world would say, ‘Who is that woman with Robert Maxwell?’ If you did it, no one would notice.” Redstone later recalled, writing with grim satisfaction that Maxwell fell off his yacht and died a few weeks after this conversation, “This is not strength. This is weakness.”

“If your competitor has an inferior theatre and the hot show, he is going to do better than you.”

Redstone’s third act would see him succumbing to this weakness. Phyllis, his wife of 52 years, divorced him in 1999. Paula, wife number two, lasted five years. He started appearing in the stories he once looked down on Maxwell for. A 

 reporter in 2010 spotted him leaving a restaurant with a new lover on his arm and asked how he impressed women. “With money,” came the reply. An ex-girlfriend claimed in a court filing that Redstone gave mistresses millions of dollars as gifts. A reality show producer got $21 million, a flight attendant got $18 million (her sister got $6 million), a student at the University of Southern California had her tuition paid for.

The allegations started to get nastier. He was accused of offering an air hostess money to clip his toenails, which according to her looked like “ancient sea scrolls”. He apparently demanded steak and sex every day from his girlfriend, against the protestations of his personal doctor. His ex-girlfriend sued him after she was removed as his designated healthcare agent, and hired a psychiatrist to examine him. So it was that in 2016, aged 92, he relinquished his chairs at Viacom and CBS after he was analysed by a geriatric psychiatrist.

In the years before he died, Redstone’s daughter Shari resolved their differences after decades of internecine warfare in which she communicated with her dad solely by fax. She saw off challenges by Manuela Herzer, Redstone’s ex-girlfriend, over who would oversee care for the old man. Shari is now the chair of ViacomCBS and president of National Amusements. “I do want people to know that if they treat me unfairly, they are going to face the battle of their lives,” wrote Redstone. But his daughter could have easily said it too.

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