Love triangle, G-strings and black book of escorts: Bernie Madoff flaunted 'culture of sexual deviance'

A lawsuit filed in state court in 2009, painted Bernie as being the boss of an animal house with 'a culture of sexual deviance' where waitresses dressed only in G-strings for drug-fueled parties

                            Love triangle, G-strings and black book of escorts: Bernie Madoff flaunted 'culture of sexual deviance'
Accused $50 billion Ponzi scheme swindler Bernard Madoff exits federal court on March 10, 2009 in New York City (Getty Images)

Bernie Madoff, the mastermind behind the biggest investment fraud in US history, died last month at the age of 82 while serving a 150-year prison sentence.

Madoff ran a vast Ponzi scheme in the early 1970s that prosecutors said swindled thousands, many of them elderly, out of their life savings. By the time Madoff was arrested in December 2008, he had defrauded as many as 37,000 people in 136 countries out of up to $65 billion. He pled guilty in 2009. His request to be released amid the coronavirus pandemic, saying he suffered from end-stage renal disease, was denied.

His immediate cause of death was revealed last week, to be hypertension, atherosclerotic cardiovascular disease, and chronic kidney disease. His kidneys had been failing for the last eight years. He was cremated in North Carolina after dying on April 14, where he’d been serving jail time. He said his dying wish was to reconcile with his grandchildren and explain his actions. "You know there hasn’t been a day in prison that I haven’t felt the guilt for the pain I caused on the victims and for my family," he told The Washington Post in 2020. 


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Bernie's 'love triangle'

Financier Bernard Madoff leaves Manhattan Federal court March 10, 2009 in New York City (Getty Images)

Madoff not only cheated his clients out of millions, he was also allegedly unfaithful to his wife, Ruth. Back in 2013, court papers filed in the case of five former employees of Madoff who were accused of helping the fraudster in his multi-million Ponzi scheme. The documents revealed that Bernie was involved a "love triangle" with one of the defendants and also enjoyed sexual trysts with a number of employees, customers, expected witnesses, and defendants before his arrest. 

"One of the defendants was in a love triangle with Bernard Madoff himself," the papers stated in a New York Daily News report. However, it was unclear whether Bernie was having an affair with former secretary Annette Bongiorno, office worker Joann Crupi, or the wife of one of the other Madoff Securities workers accused in the indictment. "The government's investigation has revealed that over the course of the multi-decade fraud alleged in the indictment, a number of Madoff Securities employees and customers - including expected witnesses, defendants and others - were engaged in romantic or sexual relationships," with one another, stated the papers, filed by the prosecution in the case against the five workers.

Sheryl Weinstein and his other girlfriends

Wife of fraudulent financier Bernard Madoff, Ruth, leaves the Metropolitan Correctional Center after visiting her husband in prison on June 1, 2009 in New York City (Getty Images)

When it came to his personal life, Bernie liked to live life king-size, and that included indulging in several sexual hookups outside his marriage. In 2009, Sheryl Weinstein, an accountant and investor who worked with the schemer, penned a tell-all book about her alleged affair with the disgraced financier, even calling him "not well-endowed." But she was not the only one he had an extramarital affair with in his life. 

According to Daily Mail, a lawsuit filed in state court in 2009, painted Bernie as being the boss of an animal house with "a culture of sexual deviance" where waitresses dressed only in G-strings for drug-fueled parties. "Madoff's affinity for escorts, masseuses, and attractive female employees was well known in the office culture, and certain feeders were allowed to participate in the conduct," the court documents filed against JP Morgan and other banks in 2009 by investor Jay Wexler, said. 

The suit added that Bernie had an affinity for escorts and kept a list of sexy masseuses in a little black book. He also had the habit of sending two "street tough men" to Harlem to get drugs for the office trysts. "Drug use in the office was described as rampant" and former employees likened it to the "North Pole," alluding to the incredible amounts of white cocaine available, the suit said. "The employees had late-night affairs in exciting places - such as their boss' sofa 'with whomever they could find,'" the Wexler suit added.

A picture of the building which houses the investment business Bernard L Madoff Investment Securities December 12, 2008 in New York City (Getty Images)

Bernie also reportedly had a number of masseuses who apparently not only gave him massages but also were prepared to give him sexual favors, a federal source told The Daily Beast. "He had a tremendous libido, like so many men in power," the source added. "He told me that Ruth just couldn't satisfy it. I suppose no one woman could," the insider said. Another person who investigated Bernie's affair said one of the girlfriends was so devastated by his profound unfaithfulness that she moved to London. "He told her lies that she discovered only after the fact, including his declarations of love to her," the source said. 

Ruth Madoff found his flirting 'irritating'

Ruth Madoff had been with Bernie since she was 13 and, according to the book, she found it hard to separate herself from him even after the conviction. But she always had her suspicions about her husband's loyalty. 

The medical examiner unit rolls out the body of Mark Madoff, son of Bernard Madoff, who was found dead of an apparent suicide by hanging December 11, 2010 at 158 Mercer St. in New York City (Getty Images)

Ruth was ever vigilant when her husband talked to any woman. "She would come right over, even if he was trying to land a client. He had the habit of cozying up to potential female investors. He'd use a low kind of sexy voice and he'd say something like, 'Don't worry, I'll be there for you. You'll never have to worry.' It irritated Ruth," a friend said. But whenever she brought up the issue about his fidelity, Bernie responded by desperately trying to gain her confidence and letting her accompany him everywhere. "He was highly motivated to make sure she thought he loved her," the friend said.

One of the reasons the two appeared so wound up with each other was that he wanted to keep her from wandering. He couldn't afford to have her confide in anyone about his ways in business. I don't think he ever even slipped—you know, dropped some hint—about his Ponzi scheme to any of his mistresses." In the end, however, she became deeply upset when revelations about his infidelities surfaced. She once said that in her mind she was “estranged” from him.

The fall of the Bernie Madoff empire took a toll on his family. The oldest of his two sons, Mark Madoff, died by suicide on the second anniversary of his father's arrest in 2010. His other son, Andrew, died from cancer at age 48 in 2014. Ruth, who had been stripped of all assets following her husband's arrest, stopped visiting him in prison and cut off all forms of communications with him. He, however, continued to write to and email her.

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