Sheryl Weinstein: Where is Bernie Madoff’s Alleged Mistress Now?

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Although there’s no denying Bernard “Bernie” Madoff orchestrated one of the biggest Ponzi Schemes in history, it was almost as if he liked the power and the success more than the money itself. Even Netflix’s ‘Madoff: The Monster of Wall Street’ alludes to this a little, but the one individual who actually vehemently indicated it all in public before was his alleged mistress Sheryl Weinstein. So now, if you wish to learn more about her — with a particular focus on her distinguished past, their reported connection, as well as her current standing — we’ve got the key details for you.

Who is Sheryl Weinstein?

It was back in the late 1980s when Wharton graduate Sheryl first came across financier Bernie while serving as the Chief Financial Officer for the renowned Jewish women’s charity Hadassah. The truth is he was already a well-established professional by this point, meaning their initial interaction stemmed from not a chance encounter but rather a meeting over Hadassah’s investments. However, the certified public accountant vividly remembers that he gave her a welcoming smile within moments, “a smile [I would] never forget… I knew instantly that he was attracted to me.”

Sheryl and Ronald Weinstein // Image Credit: The Daily Beast

Both Sheryl and Bernie were happily married, devoted parents for the outside world, yet it ostensibly didn’t stop their acquaintance from evolving into something much more behind closed doors. According to the former’s 2009 tell-all memoir ‘Madoff’s Other Secret: Love, Money, Bernie, and Me,’ the early days of their romance actually only comprised cuddling, dinner, and kissing dates. In fact, she insists it was not until 1993 that they shared a bed, following which their liaison was a blend of hot hook-ups, massages, and alcohol-fueled, weed-driven exchanges in different hotels.

Sheryl and Bernie then got so emotionally involved that she even confided in a few close friends, referring to him as “Winky Dink” due to the way he constantly blinked whenever she was around. Yet everything changed around 1994, per her own narrative, because not only did she hate being the second woman, but he also grew petrified of his high school sweetheart wife learning the truth. The duo thus parted ways following a year-and-a-half-long relationship, just to remain on perfectly amicable terms for years to come, that is, until Bernie’s ultimate arrest for fraud in 2008.

Sheryl Weinstein is Leading a Happy Life With Her Family Today

Sheryl had reportedly invested every bit of her as well as her family’s life savings into Bernie’s thriving advisory operation, leading to them sadly losing everything once the scam came to light. She and her husband, career salesman Ronald Weinstein, hence had to close doors on several possible ventures, sell off their Manhattan home, and basically find ways to get back on their feet again. It’s imperative to note that even Hadassah charity had invested more than $40 million with Bernie over the years owing to Sheryl’s work in the same, all of which went down the drain as well.

Image Credit: ABC News

The most surprising aspect, though, is that Sheryl only mentioned her alleged affair with Bernie after his trial — even while testifying against him in court, she gave no indication they were once involved. She actually referred to the fraudster as “that terror, that monster, that horror, that beast … an equal-opportunity destroyer” before stating she now views the day they met as “the unluckiest day of my life.”

Therefore, when Sheryl came out with her book mere months later in 2009, it was a complete surprise, and many also went as far as to deem it her public revenge on the man who ruined her entire life. Nevertheless, we should mention Bernie’s lawyers have since dismissed every claim made by her, all the while subtly indicating her book was just a money-grab opportunity for some sympathy and support.

“My responsibility in my family was finance, investing, and planning for our future,” Sheryl once revealed, essentially agreeing she wrote the book primarily for money. “And when this [scandal] happened the amount of guilt I felt was overwhelming. It threw me in a very deep depression. I had to start figuring out how to go on, how to pay the bills. I had no jewelry to sell, I had no art work to sell… the only thing I had to sell was my story and that’s when it started to occur to me that I would write a story and try to at least help my family financially.”

The truth is Sheryl’s husband didn’t know of her alleged extramarital affair with Bernie until 2009, yet he stood by her through everything despite being understandably furious. “I have a commitment and I’m not going to leave her hanging out there,” Rondald said back then. “I’ll wait a few months, let my emotions calm down and then I’ll see if I can forgive. Having an affair is not the end of the world, but writing a book and telling everybody about it is unacceptable… It’s unacceptable, but it’s understandable.”

Coming to her current standing, Sheryl has since preferred to maintain her distance from the limelight, which means we unfortunately do not know much about her recent experiences. However, from what we can tell, it seems like the now early 70-year-old has moved on from the past to still be married to Ronald, with whom she shares an adult son as well as a happy home.

Read More: Jodi Crupi: Where is Madoff’s Account Manager Now?