The Billionaire Skirt Chaser
Everyone knows at least one lecherous guy at work, or maybe it’s that depraved uncle who’s always ready with a dirty joke and a leer. But what if that dirty old man is a billionaire and has all the power and finances to pursue any woman he wants? Now, add to that a libido like the Energizer Bunny and we’re getting close to describing Sumner Redstone.
1. There Was A Change
Sumner Redstone was born on May 27, 1923, in Boston Massachusetts. He wasn’t, however, actually a Redstone at all. Redstone was the translation of his family’s real name: Rothstein. Sumner’s father, a theater owner, changed the name in 1940 but not for the typical reason. Yes, a lot of Jewish people in show business changed their names to sound less Jewish.
The reason for Rothstein’s name change was something much more colorful.
2. He Was No Good
Around the same time that Redstone’s father was creating his entertainment empire—a company called National Amusements—there was another Rothstein who became famous in America: Arnold Rothstein, and he was not someone with whom you wanted to be associated. This Rothstein was a gambling boss, a racketeer, and had even tried to fix a World Series. He was generally thought of as “no good”, and Redstone’s father wanted no association with him—even by name.
Sumner Redstone’s life, however, would not resemble Rothstein’s—not in the least.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
3. Sumner Redstone Was Privileged
Redstone had a very prestigious young life. He attended Boston Latin School—the oldest school in the country—and graduated first in his class from there. It was then on to Harvard where he did a bachelor’s degree in just three years. After a brief stint in the army, where he decoded secret messages from the Japanese, he went to law school back at Harvard.
By 1947, Redstone had his law degree—and a new wife named Phyllis Gloria Raphael—and was ready to start his career.
4. He Joined Dad
Redstone spent the next few years working for both the US Attorney General and then the US Department of Justice. After that, he started his own private practice. In 1954, however, the family business came calling. Dad still owned and operated National Amusements and he wanted his son by his side.
At this point, the company owned only a few movie theaters in the Boston area. Redstone had big plans for dad’s company—bigger than you can imagine.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
5. He Made A Declaration
By 1967, Redstone was the CEO of National Amusements. He looked at the company and realized something: They were only involved in distributing films. Redstone thought that there would always be distributors, but what was really important was the content of the entertainment. Redstone had an epiphany and it became a catchphrase: “Content is king”.
With this as his motto, Redstone began to change National Amusements into something much, much larger than his father could have dreamed of.
6. He Was At The Center
Once Redstone had realized that “content is king,” he started to invest. He didn’t waste any time and put the company’s money into the top creators of content in the film industry: Paramount Pictures, Columbia Pictures, Orion Pictures, and 20th Century Fox. Redstone knew that the future was in making movies, and he positioned his company—and himself—to be at the center of it all.
Life was finally getting exciting for Sumner Redstone—until a disaster almost ended it completely.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
7. He Had To Save Himself
In March of 1979, Redstone was staying at the Copley Plaza Hotel in Boston. An angry ex-employee of the hotel arrived in the middle of the night and lit fires around the building. When Redstone woke up, he was at the center of an inferno. Desperate to survive the blaze, Redstone climbed out of his hotel room and hung by his fingertips from the third-story window.
You see, Sumner had something to live for: He was going to revolutionize television forever.
8. He Saw The Future
Back in those days, TV networks could not syndicate their own shows to air them as reruns. For this reason, CBS started a company called Viacom International. Redstone saw a future in reruns, and in 1986 he bought the company for National Amusements. This gave Redstone access to shows that had once been hugely popular and would again attract a huge audience. It wasn’t just CBS shows that he had under his control. CBS had bought I Love Lucy and other popular programs like The Mary Tyler Moore Show and The Cosby Show.
Redstone had a vision: He wanted to see Americans planted on their couches and glued to their TVs—and that's exactly what he got.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
9. He Had To Pay A Premium
Once Redstone had Viacom, he went for something even bigger: Paramount Pictures. Unfortunately, he wasn’t the only one who wanted it, and he got into a battle of the bids with heavy hitters Barry Diller and John Malone. But right in the middle of the battle for Paramount, Redstone’s wife made a devastating announcement: She wanted a divorce and she wanted it now.
10. They Talked Her Out Of It
A divorce was the last thing Redstone had time for when he was busy trying to buy a huge company like Paramount. Somehow, Redstone’s people talked Phylis out of the divorce and she withdrew. He would soon make her regret it. However, this freed up Redstone to pursue the purchase of Paramount even harder. Redstone bid like there was no tomorrow and eventually won the opportunity to buy Paramount. But had he paid too much?
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
11. He Made Hits
Redstone was where he wanted to be, creating the content for Hollywood films, and he wasn’t about to waste any time. While he owned Paramount, they released Saving Private Ryan, Braveheart, and one of the top-grossing movies of all time: Titanic. He also started several franchise films: Mission Impossible, Transformers, Star Trek, and Paranormal Activity.
He was at the top of the Hollywood game and nothing could stop him—or so you’d think.
Titanic (1997), Paramount Pictures
12. She Walked Away
In 1999, when Redstone was in the middle of a huge deal—this time to buy CBS—Phylis Redstone again asked for a divorce. It seemed that Phylis was in a habit of waiting for the exact wrong moment to do this. And this time, she meant business. Phylis Redstone quietly asked her husband for a colossal $3 billion settlement. Maybe she thought her husband would be too busy buying CBS that he wouldn’t notice how much she was asking for. Sources close to the family said that she walked away with a measly $100 million.
Redstone was now 76 years old, single, and ready to mingle—but were the women of the world ready for him?
Nightline Up Close(2002/2003), ABC News
13. It Was A Mission Possible
Around the time of his divorce, Redstone was romantically pursuing a woman named Christine Peters. Peters was a movie producer and Redstone made it his mission to seduce her. After splitting with his wife, he moved himself to Hollywood, where he could continue to make the moves on Peters. Peters didn’t seem to want anything to do with the much older Redstone, so she quickly made off to Canada to make How to Lose a Guy In 10 Days. It may have taken more than 10 days, but Peters did manage to lose Redstone.
But Redstone was impatient. When he lost out on Peters, he quickly looked elsewhere for a mate.
14. There Was A Difference
In 2002, Redstone met a school teacher named Paula Fortunato, whose name seems like a red flag as to what she was after. Redstone married her anyway, and it lasted for just over five years. Funny thing is, it was him, not her, who asked for the divorce. He said they had “irreconcilable differences”. Well, he was 85 and she was 39, so that was one difference they had.
Marriage trouble wasn’t Redstone’s only problem: He was also in debt.
15. It Was Suspicious
While Redstone’s second marriage came to an end, his financial situation also seemed ill-fated. Somehow his company was in debt for $1.6 billion. To add to his financial woes, his divorce was going to cost him a cool $5 million out of his own pocket. Fortunato had signed an agreement to get a million for each year she spent with him. What’s suspicious is that the amount was set to cap at $5 million. It seemed that Fortunato wanted out as soon as she could get out.
Once again, Redstone was a free man—but he was randier than ever.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
16. He Wanted Her
In 2008, the newly single—and 85-year-old—Redstone was traveling on one of CBS’s private jets. He took one look at the 26-year-old flight attendant Malia Andelin and decided he wanted her. His first question was about whether she liked to be hit in the bottom or not. It didn't stop there. Redstone pestered Andelin for the entire flight. When they landed, Redstone insisted on getting her phone number, which she smartly refused to give.
Redstone did not like getting no for an answer. The games were about to begin.
Nightline Up Close(2002/2003), ABC News
17. He Had A Theme
Andelin had refused to give Redstone her phone number, but being a powerful man—and in business with the jet company—he got it. That’s when the insistent phone calls began. On one occasion, he left her a message on her voicemail. While this seems like normal behavior, this voicemail had a cheesy theme from one of Redstone’s own movies. In it, he admitted that getting a date from her may seem like a “mission impossible”, but he was going to make it a “mission possible”.
Ugh! Sadly, this pitch for romance worked—kind of.
18. She Went For Him
Andelin, who had lost money in the financial crisis, desperately needed cash. She began to pester the jet company for more flights, but, for some reason, the company suddenly had no shifts for her. Andelin then realized that in some of Redstone’s messages, he was implying that it was up to him if she got any more work as an attendant. Andelin had soon had enough, and she took the bull by the horns.
She called Redstone directly and left him an angry message: She wanted to know when she could get her job back.
19. He Was An Animal
And what was Redstone’s response to Andelin’s angry voicemail? He sent her a gift. Andelin soon received a handbag by Judith Leiber in the mail. The designer bag had crystals all over it and retailed for about $5,000. The handbag was in the shape of a panther and the note inside, while lacking in sophistication, did get to the point. It said: “I’m a panther and I’m going to pounce”.
Andelin wanted her job back, and nothing she’d tried had worked. Would dinner with this old man really be that bad?
Nightline Up Close(2002/2003), ABC News
20. They Were Suddenly Alone
Andelin’s dinner with Redstone went off okay, but the ride home in the limo didn’t. When they got in the car after the meal, the driver didn’t get in with them—a trick probably arranged by Redstone. Andelin was alone with Redstone, and he was suddenly trying to get his hand in her blouse. Andelin was in shock. She pushed the old man away and managed to get out of the car.
She later said that she had no memory of how she got home. Surely, Andelin had learned her lesson. Or had she?
21. She Had Nothing To Worry About
After a few apologies—by email and in person—for some reason Andelin agreed to see Redstone again: This time at his home. When she arrived, a man named Carlos Martinez greeted her and immediately tried to help calm her nerves. He assured her that she would not be alone with Redstone and that there was “nothing to be afraid of”.
If I heard that upon entering someone’s home for dinner, I’d head in the other direction. Andelin, however, did not.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
22. He Paid Her Well
Redstone managed to stay on his best behavior that night, and Andelin agreed to a second date, a third, and then more. After one of these dates at his mansion, Redstone handed her a check for $20,000. This was about the same amount she would have earned working on the jet that month. Redstone knew what he was doing: He was letting her know that this was like a job. But would she accept?
23. He Was Crude
Andelin did go out with Redstone mostly because he told her she could quit her job on the jet and spend her time going to dinners and high society functions with him. She did say that in her opinion, Redstone was “foul-mouthed and crude”. She once heard him call then-President Obama the worst insult you could give a Black President—and he did it quite loudly.
Andelin admonished Redstone for his misstep. She did, however, also continue to see him.
24. He Wasn’t Satisfied
Against her better judgment, Andelin started regularly hanging around the Redstone home. Redstone explained to her that she didn’t need her job, and that her only occupation was to be his date at parties, dinners, and fancy Hollywood premieres. Andelin reluctantly agreed to this. Redstone had achieved what he’d previously thought was impossible: Andelin was his.
You’d think this would finally satisfy him. Nope, his Energizer Bunny libido needed more.
25. He Found Another
While still “dating” Andelin, Redstone went searching for yet another woman to be his companion. He came across Rohini Singh, whose claim to fame was being featured in a tell-all article in Los Angeles Magazine about dating in Hollywood. Redstone took a shine to young Singh, and to keep her around he offered her a job at CBS’s Showtime. It didn’t seem to matter that Singh had no experience, and there was a hiring freeze at the time.
So, Redstone had Andelin and he had Singh. Was there room for more? Absolutely!
Nightline Up Close(2002/2003), ABC News
26. He Went All Out
Redstone next met Terry Holbrook, who had been both a model for Ford and a cheerleader for the Houston Oilers. Redstone didn’t just entice this one with dinners, parties, or even a job. He went full out with Holbrook: He bought her a house worth $2.5 million, paid for the upkeep of her show horses, and gave her a monthly salary of $4,500. He went even one step further with Holbrook: He made her a “beneficiary of his trust”.
Redstone seemed to have an entire staff of women at his beck and call. There were, however, even more if you count the ones for casual dating.
Victory Road with Lee Benton (TV Series),Lee Benton
27. He Found An Unusual Source
Redstone had the women he was paying to be his companions, but he also wanted more women just for dating. But where was he going to find these women? When Redstone was hard up for a date, he turned to a surprising source: his grandson. Brandon Korff said that his grandfather would call him up in the middle of the night to ask him to hook him up with women. Korff didn’t mind helping out his grandfather...until things got a little too close for comfort.
28. He Went Too Far
Korff had the odd job of hooking his 86-year-old grandfather up with women, but at the 2009 MTV Awards, things got a little weird. Before and during the ceremony, Redstone began flirting with Korff’s own girlfriend in front of everyone. Korff had had it. He called up Patti Stanger who was hosting a show on HBO called Billionaire Matchmaker. He threw $120,000 at Stanger and asked her to take care of his grandfather’s needs.
Wikimedia Commons, Fred Rockwood
29. She Was A Fembot
While Stanger was busy finding suitable dates for Redstone, he was busy finding dates of his own, but suitable isn't the word I’d use. In 2010, Redstone turned up with a woman on his arm, a “tall, tan, fembot-like blonde”. The woman turned out to be Heather Naylor, the lead singer of the Electric Barbarellas. And who were the Electric Barbarellas? This was the band that Redstone was pushing MTV to make a reality show about. MTV’s parent company, you see, was Viacom: owned by Redstone.
Things were about to get very messy.
The Late Late Show with Craig Ferguson, Worldwide Pants
30. They Played Late
Redstone wanted the Electric Barbarellas to appear on CBS. In fact, he was adamant that they appear, and the man in charge of programming reluctantly allowed them to. You see, the word on the street was that the Electric Barbarellas were awful. So, CBS wanted to put them on very late—when most viewers had gone to bed. This ended up being on The Late Late Show with Craig Ferguson. They didn’t put the band on until the end of the show, which clocked in at 1:30 in the morning.
Problem solved. Except Redstone wasn’t happy with a brief late-night appearance—not one bit.
The Late Late Show with Craig Ferguson, Worldwide Pants
31. He Pushed
Once Redstone had gotten Heather Naylor on CBS, he wanted her on MTV. Of course, the people at MTV wanted about as much to do with the Electric Barbarellas as CBS had. Redstone, however, was unstoppable. He pushed and he pushed. Oh, and he also spent. It cost Redstone a half a million dollars just to send the band to New York for auditions at MTV.
If the Electric Barbarellas were as awful as people said they were, how do you think these auditions with MTV would go?
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
32. They Were Unwatchable
The auditions didn’t go well, but Redstone made the show happen anyway. In the meantime, Peter Lauria at The Daily Beast got wind of how bad the Electric Barbarellas and Redstone’s new girlfriend were. Someone from inside told Lauria that the MTV show featuring The Electric Barbarellas was “unwatchable and the music just as bad”.
When Redstone heard what Lauria was saying about his girlfriend’s band, he went ballistic.
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
33. He Wanted The Truth
Redstone called The Daily Beast’s Lauria directly. He wanted to know who it was that had said those horrible things about his girlfriend’s band. Redstone had his theory—it was a “young male executive at MTV”—but he wanted to know for sure. Redstone promised Lauria all kinds of protection if he revealed his source. He also promised him some financial rewards.
All of this was potentially embarrassing for Redstone. But then it just got worse.
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
34. He Made A Threat
While trying to pry the name of Lauria’s source, Redstone went too far. He mentioned that they had no plans to murder the source—they just wanted to talk to him. Um…isn’t there an unwritten rule that when someone mentions murder, it means that murder is on the table? Of course, this entire call to Lauria would be mortifying to Redstone if it ever got out.
The thing was: Lauria was taping the phone call.
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
35. It Was A Hit
Lauria took his taped conversation with Redstone and made it into a scandalous story for The Daily Beast. But you know what they say: There’s no such thing as bad publicity. Lauria’s story made MTV’s The Electric Barbarellas into a hit. The premiere episode drew a record audience and it actually ended up being the number one cable series on that night.
And the bad news? This means people actually saw it.
36. He Shelled Out
The reviews for The Electric Barbarellas were beyond bad, some called them scathing. New York Magazine said the show was: “hyper-contrived” and “a mess”. People quickly stopped watching it, and MTV got to do what they’d always wanted to do: cancel it outright. Redstone, however, didn’t give up on Naylor, and he followed the failed show with his usual showering of gifts. This included stock shares and some good old-fashioned cash. The total he shelled out to Naylor came in at $20 million.
Was Redstone’s fondness for needy women waning? Not even a little bit.
37. She Took Over
Now remember, Redstone’s grandson had hired Patti Stanger to find women for his grandfather. Redstone had turned out to be Stanger’s Everest: She couldn’t find him a match. Part of the reason that Redstone wasn’t falling for any of her suggested women was because he had fallen for Stanger herself. Stanger did not know the word quit, so she found someone who was a mini version of herself.
This was Sydney Holland, and I think “trouble” may have been her middle name.
38. She Got Showered
Sydney Holland was just 29 years old when she met Sumner Redstone, and 30 when he handed her a nine-carat diamond ring. It didn’t take long for Redstone to start showering her with the usual gifts. Holland liked roses and orchids; she also loved Porsches. Redstone bought her all these and more: jewelry, art, and, as usual, plain old cash. Soon, Holland was worth an estimated $9 million.
There was, however, something about Holland that Redstone didn’t know. Something scandalous.
39. She Had A History
One of Holland’s previous relationships was with Bruce Parker—a golf executive who was worth millions. The two had met at an AA meeting as Parker had issues with addiction. What Holland was doing at the meeting is anyone’s guess—maybe looking for dates? Holland was soon engaged to Parker and, as you might guess, out to get his money. Parker, however, was only in his 50s and it seemed that waiting for his passing was not an option for Holland.
Let’s just say she took matters into her own hands.
40. She Knew His Weakness
Holland knew about her fiance's troubles with addiction, and yet somehow the two ended up in bed and using—well, at least Parker was. The lethal combination of narcotics and intercourse proved too much for Parker. He had a cardiac episode, and by the morning light, he was no more. Holland quickly turned around and went for the estate. Parker’s family, however, wasn’t about to let that happen. Holland got a measly $164,000 and a nice set of luggage for her trouble. She was sent packing.
So, this was the kind of woman Redstone was welcoming into his life. Let’s see if he fares better than Parker.
41. He Delivered The Cash
Tim Jenson was a hired driver who worked for Paramount, and his job was driving Redstone around. When Holland turned up in Redstone’s life, Jenson suddenly had a new duty. Holland gave him checks, which Jensen noticed she’d made out to “cash”.
Jensen was to take the checks to the bank, cash them, then bring the money back and give it to Holland. Jensen knew what Holland was using the cash for: to pay women who shared a bed with Redstone. When Jensen eventually complained to his boss about hauling large amounts of cash to pay for these women, Holland had him fired.
Holland was slowly gaining control over Redstone’s life. And she was just getting started.
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
42. It Was Three’s Company
One of the women whom Holland arranged to satisfy Redstone’s needs told a startling story. When she arrived in his bedroom, she made a shocking discovery: They weren't alone. Apparently, Redstone’s nurse was going to watch the entire ordeal. If that wasn’t bad enough, the nurse was going to play a role in their little tryst. The nurse’s job was to tell the woman what she could and couldn’t do in bed with Redstone. By the way: The woman also reported that Redstone was barely conscious throughout the act.
Redstone was losing control of his life—and it was about to get worse.
43. She Took Over
Eventually, Redstone asked Holland to move in with him. Holland jumped at the opportunity and quickly took over…pretty much everything. In addition to finding women for Redstone to sleep with, she also did the jobs of secretary, manager, and even—as Redstone got older—nurse. If you think that Holland had it easy, you're wrong. She had all the above roles to fulfill, and then there were also “the rules”.
44. He Had Rules
If Holland wanted to continue to be Redstone’s companion, she had to follow the rules. Holland had to be present with Redstone for all meals except for breakfast. When it came to bedtime, Holland had no choice but to go to bed at the same time as Redstone. In addition, Redstone would not permit Holland to take any overnight trips without him. But one rule was the worst by far: She had to stop seeing her friends.
And what about the rules for Redstone? There were none. According to their arrangement, Redstone could even have another girlfriend—which of course he took full advantage of.
Sumner Redstone, Chairman Emeritus of Viacom-CBS, CBS News
45. They Teamed Up
While living with Holland, Redstone had time for another girlfriend: Manuela Herzer. It was when Herzer moved in with Redstone and Holland that things got messy. Instead of being enemies, Holland and Herzer soon teamed up against Redstone. First on their evil agenda was getting rid of staff who were not loyal to them.
More worrisome still, they strictly controlled who had access to Redstone. They even turned away immediate family members. Once they had a system to keep Redstone away from his family, they took it to the next level.
Remembering Sumner Redstone (CBS Sunday Morning), CBS News
46. They Gaslighted Him
Redstone was starting to wonder why his own family wasn’t trying to contact him. The truth was that they were—he just wasn’t getting the messages. Holland and Herzer were telling him that his family just didn't bother to call. They then went even further: They told Redstone lies about his daughter Shari.
They said she was a liar who was only after his money. Sounds like Holland and Herzer needed to take a look in the mirror. Holland and Herzer seemed unstoppable—until someone stopped them.
47. She Got Rid Of The Competition
The thing that broke up Holland's scheme to get Redstone’s money was lust. It turned out that Holland had fallen for a man: George Pilgrim. Pilgrim had two strikes against him: He was a former soap opera actor…oh, and a convicted felon. Holland was using Redstone’s money to book private jets to go have amorous meetings with Pilgrim. She never even saw the betrayal coming.
Herzer used the information she had on Holland and double-crossed her friend. Holland was out. Herzer now had Redstone all to herself: what would she do next?
48. They Wanted Her Out
Once Herzer had Holland out of the picture, she’d get all of Redstone’s money for herself. But things didn’t work out that way. Once people in Redstone’s life saw what Holland had been doing behind their backs, they realized that Herzer was no better. A group consisting of Redstone’s relatives and his nursing staff joined forces and got Herzer out of Redstone’s life.
It seemed like the whole Holland/Herzer ordeal appeared to be over. But don’t count on it. Now it was time for the lawyers to step in.
49. The Court Cases Started
Once Holland and Herzer were out of the mansion the court cases could begin. The first case was Redstone charging Holland and Herzer with elder abuse. The two women then turned around and charged Redstone’s daughter with secretly working with Redstone’s nurses to get intimate information about Holland and Redstone’s activities.
Holland and Redstone eventually came to a private agreement about their case, but Herzer didn’t fare too well. She had to pay the Redstone family $3.25 million for all the free stuff she’d gotten.
50. He Lost The Thrill
Sumner Redstone was 92 years old when Holland and Herzer got the boot from the Redstone mansion, and he was 96 when he finally settled accounts with Herzer. It seemed that it was finally time to call it quits on the skirt-chasing. With that finished, there wasn’t much left for the old man to do. On August 11, 2020, he passed peacefully—of unreported causes—in his home. He was 97 years old.
51. He Wasn’t All Bad
Yes, Redstone spent an awful lot of money convincing women to fall in love with him. He also, however, spent huge amounts on charity. Some of his over a million dollar donations went to Autistic children, orphans in Cambodia, cancer and burn recovery victims, and helping the illiterate. It turned out that his showers of gifts were not just for his lady friends. He actually did a lot of good for the world.
