Sumner Redstone, 93, 'paid out $70million to women who provided nothing more than sexual favors': Billionaire's ex who wants half his estate claims he gave $21m to a mistress and $18m to a flight attendant

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Explosive new court documents filed by Sumner Redstone's ex in response to his elder abuse suit against the woman claim that the 93-year-old paid out over $70million to women who 'did nothing more than provide sexual favors.'

Sydney Holland, 45, writes in papers that were filed in Superior Court of California, County of Los Angeles that the billionaire businessman gave $21million to a former mistress who is an aspiring reality television producer; $18million to a flight attendant on the CBS corporate jet and $6million to the flight attendant's sister who he 'slept with'.

She also claims he paid out $11million to a woman he met through Millionaire Matchmaker Patti Stanger; $7million to another mistress; $6million to a friend of his grandson's girlfriend along with a job at Showtime; and $1.5million to a third mistress.

Redstone also gave an undisclosed amount to an ex-fiancee and paid college tuition for a student at the University of Southern California, Holland claims in the court documents.

She also insists that Redstone spoke about marrying her and adopting her three-year-old daughter Alexandra, who she gave birth to at Redstone's home as he stood by her side.

She is now asking for half of his cash, stock and non-real property upon his death, saying that he broke a verbal agreement the two had when he had her removed from his Beverly Park mansion after learning she was having an affair last year.

Holland is also asking to be named a beneficiary for half of Redstone's mansion. 

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Bombshell: Sumner Redstone's ex claims in court papers that the 93-year-old gave out over $70m to women who 'did nothing more than provide sexual favors' (Redstone and Sydney Holland above in 2013)

Big bucks: Sydney Holland, 45, claims that Redstone gave $21million to a former mistress and $18million to a flight attendant on the CBS corporate jet (above with Holland's daughter Alexandra)

More money: Holland also claims Redstone gave $6million to the flight attendant's sister after sleeping with her and $6million to a friend of his grandson's girlfriend (Holland, Redstone, Manuela Herzer and Shari Redstone above)

'For five years, Sydney and Plaintiff Sumner Redstone enjoyed a loving, romantic relationship. Their courtship began in the fall of 2010, when Redstone hired Patti Stanger, “The Millionaire Matchmaker” to find him a girlfriend who was not only young and beautiful, but also intelligent, funny, and who shared Redstone’s Jewish faith,' read the court papers.

'Patti knew Sydney was the “perfect match,” and contacted her right away. Almost immediately, the pair hit it off. They took long drives down the Malibu coast, listening to Tony Bennett and Frank Sinatra. They went to restaurants and shared Redstone’s favorite dessert, chocolate mousse.'

The 9-carat ring Redstone gave to Holland (above)

A year later Redstone proposed with a '9 carat yellow canary engagement ring, and asked her to move in with him.' 

The filing goes on to say: 'He repeatedly told Sydney that he wanted to spend the rest of his life with her and that he wanted to adopt her daughter. He added her daughter to his Will. He assured her that he would take care of them for the rest of their lives.'

The relationship was not easy however according to Holland, who writes of the demands that Sumner allegedly made of her.

'For many years, Sydney had to be home for lunch and dinner with him 7 days a week because Redstone expected her to be. When Redstone went to sleep, he demanded she go to sleep as well – even if she didn’t want to,' claim the court documents.

'Redstone forbid her from going out at night without him; again, she complied. She could not travel or take trips without him or spend time with friends. Her friendships withered and died. But, as always, he could do whatever he wanted.'

That is why Holland claims she had a short-lived affair, which led to Redstone kicking her out of his home.

Holland also claims that despite this Redstone has twice been to see her young daughter this year. 

Now she wants what she claims she is entitled to for her years with the executive.

'As was his habit, Redstone was always extremely generous to Sydney, albeit not without a certain amount of self-interest,' reads the complaint. 

'He wanted her attention solely on him, and, early on, he undertook to support her financially to encourage her dependence on him.'

Love notes Redstone gave to Holland (above)

The complaint was filed in response to the suit that Redstone submitted back in October against Holland and his ex Manuela Herzer. 

The lawsuit, filed by Redstone's attorney Robert Klieger at the Superior Court of California, Los Angeles County, stated: '[Herzer and Holland] manipulated and emotionally abused Redstone to get what they wanted - jewelry, designer clothing, real estate in Beverly Hills, New York, and Paris, and money, lots of it.

'By the time Redstone threw Herzer and Holland out of his home, and out of his life, last fall, they had taken him for more than $150 million and left him in debt on account of the immense tax obligations triggered by those "gifts."'

The lawsuit also claims that on May 19, 2014, the women convinced Redstone to sell his vested stocks and then had him deposit $45million into each of their bank accounts.

Herzer and Holland allegedly did this by taking advantage of Restone's declining health and his sexual attraction to the two, specifically Holland, according to the lawsuit. 

The lawsuit also breaks down some of the ways in which Herzer and Holland allegedly spent Redstone's money.

'In 2014 alone, Holland charged more than $2million to Redstone's  Visa and American Express cards including $63,612 at mario Jewelers of Beverly Hills, $58,461 at Saks Fifth Avenue, $57,912 at Yves Saint Laurent, and a staggering $752,737 at Tracie Butler Interior Design (little if any of which was spent on furnishings for Redstone's Beverly Park residence),' reads the complaint.

'Herzer charged $1.5million to Redstone's cards during that same 12-month period, including $128,780 at Barney's, $82,624 at Hermes, $54,212 at Miu Miu, and $34,147 at Chanel.' 

The lawsuit also claims that the women kept Redstone away from his family and friends in order to have full control of him, and that on at least two occasions they had Adavan or a similar drug administered to him in order to keep him under their command.  

The lawsuit comes just a few months after Herzer filed her own lawsuit against Redstone.

The judge in the case made the decision to dismiss that $50million suit, saying that Redstone was mentally competent, despite the claims.

'There is no good cause for further judicial involvement where the court has now heard directly from Redstone that he has lost trust in Herzer, does not want her in his life and instead wants his daughter Shari to look after him as necessary,' said Los Angeles County Superior Court Judge David J. Cowan.

'Herzer herself insisted from the outset of this case that the court hear from Redstone. Redstone had not otherwise intended to appear at trial in view of the medical risks and difficulties involved in doing so. However, Redstone's testimony has ultimately defeated her case.'

Redstone and his family are seen at his Star ceremony on Hollywood's Walk of Fame in 2012. Redstone's lawsuit claims that the women kept Redstone away from his family and friends in order to have full control of him

In a taped deposition played at the start of the trial, Redstone blasted Herzer, becoming vulgar at times.

The first question asked of Redstone during his taped deposition is; 'Who is Manuela Herzer?'

An interpreter, on hand to help Redstone, jumped in at that point to ask that the question be asked 'slowly,' but was cut off by the billionaire mogul as he responded; 'She is - Manuela is a f***ing b****.'

Redstone went on to repeat this statement three more times over the course of the deposition.

Herzer filed her lawsuit last November, one month after she was suddenly banned from Redstone's Beverly Park mansion and removed as his primary caretaker.

She was to receive '$50 million and Redstone's Beverly Park home, worth roughly $20 million' upon his death according to a court filing earlier this month in the Superior Court of the State of California.

That money would come on top of the $70 million in cash and assets Redstone's daughter Shari said her father gave to Herzer since just 2009 while she lived near his home.

The money from the will has now been directed to Redstone's charitable foundations.

A deal negotiated between lawyers for both sides that would have paid Herzer a reported $30million to drop her case fell apart at the eleventh hour for unknown reasons.

Almost immediately after her $50 million lawsuit fell through, Herzer filed a new suit against the billionaire's family and medical team, seeking at least $70 million.

The suit names Shari Redstone and sons Tyler and Brandon Korff, Sumner's house manager Isileli Tuanaki and lead nurse Jeremy Jagiello, alleging the group conspired to cut her out of the estate.

'Shari organized and implemented what would eventually become a successful campaign to turn Sumner against Herzer and strip Herzer not only of her role as his health care agent, but also of her inheritance,' documents allege.

The suit seeks damages against the group who she holds responsible for what Herzer called 'criminal acts in intentionally destroying [her] special relationship with Sumner and causing Sumner to disinherit her.' 

Holland is now asking for half of Redstone's fortune when he dies, saying the two were engaged and he looked into adopting her 3-year-old daughter (above)

Shortly after Holland split up with Redstone, George Pilgrim (above) came forward and revealed he had been in a relationship with her

Redstone could not recall exactly how long Manuela lived with him in his deposition, or the years they were together, but he was able to recall that he kicked her out of his home in October 2015.

That answer came after much back and forth between Herzer's lawyer and Redstone's interpreter, with both parties wanting to be certain that Redstone had indeed said 'October 2015.'

It was also during this exchange that the interpreter requested that someone 'adjust' Redstone's dentures.

Redstone was then asked if Herzer helped him with his health care when she lived in the home, and admited that she did in fact do so while staying at his residence.

When asked however what she did to help him, Redstone responded by saying; Manuela is a f***ing b****.'

Redstone then had problems speaking and a board was brought out so he could point to letters while Herzer's lawyer repeated the question multiple times.

After spending three minutes trying to get an answer to the question to no avail Herzer's lawyer agreed to move on with the questioning.

Herzer's lawyer also skipped over the next question when he got no response after asking Redstone what his birth name was, with the mogul having convinced his father when he was a teenager that the family should change their last name from 'Rothstein' to 'Redstone.'

Moving on he showed Redstone a photo of himself with Herzer, asking when it was taken.

Redstone responded to this by saying; 'Who cares.'

Upon further questioning he was able to say that the picture was taken at Paramount while he and Herzer were dating. He also admitted that he was in love with Herzer at the time.

Redstone then answered in the affirmative when asked if Herzer stole money from him, but was unable to give an amount when pressed for detail.

He also answered the next question in the affirmative when asked; 'Did you ever say Manuela was the love of your life?'

For his final question, Herzer's lawyer asks Redstone if he said anything to his ex as she was leaving his home or gave her a reason as to why he was kicking her out.

Redstone responded to this by saying 'no,' and when asked why told the attorney; 'Because she's a f***ing b****.'

Gabrielle Vidal, a member of Redstone's legal team, had far better luck getting answers out of the nonagenarian while questioning him during the deposition.

Redstone then had problems speaking and a board was brought out so he could point to letters while Herzer's lawyer repeated the question multiple times.

After spending three minutes trying to get an answer to the question to no avail Herzer's lawyer agreed to move on with the questioning.

Herzer's lawyer also skipped over the next question when he got no response after asking Redstone what his birth name was, with the mogul having convinced his father when he was a teenager that the family should change their last name from 'Rothstein' to 'Redstone.'

Moving on he showed Redstone a photo of himself with Herzer, asking when it was taken.

Redstone responded to this by saying; 'Who cares.'

Upon further questioning he was able to say that the picture was taken at Paramount while he and Herzer were dating. He also admitted that he was in love with Herzer at the time.

Redstone then answered in the affirmative when asked if Herzer stole money from him, but was unable to give an amount when pressed for detail.

He also answered the next question in the affirmative when asked; 'Did you ever say Manuela was the love of your life?'

Redsone's lawsuit claims that on May 19, 2014, the women convinced Redstone (pictured with Megan Fox in 2014) to sell his vested stocks and then had him deposit $45million into each of their bank accounts

For his final question, Herzer's lawyer asks Redstone if he said anything to his ex as she was leaving his home or gave her a reason as to why he was kicking her out.

Redstone responded to this by saying 'no,' and when asked why told the attorney; 'Because she's a f***ing b****.'

Gabrielle Vidal, a member of Redstone's legal team, had far better luck getting answers out of the nonagenarian while questioning him during the deposition.

O'Donnell's first witness confirmed almost everything he said in his opening statement.

Dr. Stephen L. Read, a geriatric psychiatrist hired by Herzer, was the first medical expert to take the stand in the trial.

He testified under oath that in his medical opinion Redstone has dementia and suffers from possible delusions. He also said he was not of sound mind when he made the decision to kick Herzer out of his home and remove her from his health care directive in October.

'He does have major neurological problems,' said Dr. Read of Redstone.

Dr. Read went on to call Redstone 'severely impaired' saying he was a 'thin shadow' of his former self.

'He did not have the requisite mental capacity to understand the changing of his health care directive of October 16, 2015,' said Dr. Read.

He also spoke about Redstone's behavior and his 'propensity to erupt in anger' at any given moment.

'When anger takes over reasoning is ablated. That removes his inability to think about this, access memory, consider alternatives to do the things that are required to make an informed decision,' said Dr. Read.

He went on to say that removing Herzer from his life made matters worse and had 'potentially terrible effects' on Redstone.

He then detailed his January 29 examination of Redstone, which was granted by the court at Herzer's request.

The lawsuit comes just a few months after Herzer filed her own lawsuit against Redstone. The judge in the case made the decision to dismiss that $50million suit. She is pictured outside court during the proceedings, where she wanted to be put in charged of his estate 

Sumner Redstone's daughter Shari Redstone (center) leaves a downtown courthouse in Los Angeles during hearings in the lawsuit filed by Herzer

During that session Dr. Read said that Redstone repeatedly stated that Herzer stole $40million from him and was confused as to the amount of money he had previously planned to leave her in a trust.

Dr. Read also spoke about how difficult it was for Redstone to communicate and how hard it was to understand him when he did speak.

He also spoke about Redstone's physical abilities, saying; 'Mr. Redstone can't hold a pencil. He's completely disabled. For the most basic acts of a human's life, he can't do them himself.'

Redstone stepped down from his role as chairman at both CBS and Viacom in February, becoming chairman emeritus at both and handing over the reins to Les Moonves and Philippe Dauman respectively.

Herzer was banned from the billionaire media mogul's Beverly Park mansion in October for reasons that remain unclear.

She began dating Redstone - who is worth an estimated $5.2billion - in 1999, and remained a close friend and confidante after the two split, moving to a house just down the street from him.