Meet Madoff's Mistress

When Bernie told his secretary he was going to lunch with a "pain in the ass" investor, he was really meeting his blond girlfriend. Allan Dodds Frank profiles the newest player in the Madoff saga.

08.14.09 6:15 AM ET

“She’s a pain in the ass, but I guess I have to go out with her for lunch,” Bernard Madoff would say to his secretary about the aggressive blond woman nearly a decade younger than his wife Ruth, who would show up at his Lipstick Building office and demand that he leave in the middle of the day.

Eleanor Squillari, Madoff’s assistant, told The Daily Beast she now realizes Madoff was just trying to throw her off the scent about his hotel frolics with the demanding client. Sheryl Weinstein, now 60, was a younger, bigger, bustier, feistier version of Ruth Madoff and until a few years ago, used to “drop in” on Bernie fairly regularly.

I asked: “Can you tell me how well you knew Bernie?” and she said: “ I knew him through business, that’s all.”

Now the world will know about the escapades of Bernie and Sheryl Weinstein, a woman who met Madoff 21 years ago, an event she testified in court was “the unluckiest day of my life.” Weinstein has written a tell-all book for St. Martin’s Press, “Madoff’s Other Secret: Love, Money, Bernie and Me,” due out August 25th, that promises to disclose the between-the-sheets activities – the gonif-meets-gonads account – that she hopes will resuscitate her finances, even if it engulfs her marriage.

A tip came to me and Bloomberg News, where I was covering Madoff early on, that a woman claiming to be his mistress was shopping for possible literary representation. She wanted to write a book because her entire family had gotten wiped out by the man she had slept with secretly. Maybe she had gone to the University of Buffalo; her first name might be Cheryl or something like that. More reporting and examination of the victims’ lists led to Sheryl Weinstein, personally, and her one-time employer, Hadassah, the leading Jewish woman’s charity.

Most of her life seemed to have some connection to Madoff. While at Haddasah, the charity invested $40 million with Madoff, according to a letter to its supporters – it stopped adding principal in 1997, the same year Weinstein left her post at Hadassah. At that point, her apparent livelihood centered around publishing a trade newsletter and Web site called “Laundry Today.”

Click Image to View Our Gallery of the Madoffs at Play

GI / BM / Getty Images

I first called Weinstein months ago, asking whether she was a Madoff victim. With an amused inflection, she answered: “Well, yeah.” She refused to disclose any details. “I’m really not up for talking right now,” she told me, “but if you give me your number, maybe I’ll call you back.” In another call, she confirmed she had a business relationship. but declined to say anything about whether she had had “a personal relationship.”

Weinstein's "Laundry" office – which also housed her "Eternity Road Publishing" venture – was at 57 West 57th Street, just nine blocks from Bernie's office. When I visited the 14th floor office a couple of months ago, it was clear through the frosted-glass door that it was vacant, a fact confirmed by a building employee. The newsletter’s annual sales ran $500,000 to $1 million, according to

The apartment Weinstein shared with her husband of 37 years, Ronald, at 360 East 72nd Street in Manhattan, was refinanced a few years ago, with all the money then invested with Madoff. When the Ponzi scheme collapsed, the couple was forced to sell the two-bedroom apartment at the distressed price of $1.2 million.

Her son Eric had served as an intern at Bernard L. Madoff Investment Securities one summer, admiring Bernie enough to put all his money with his mentor.

Among the thousands of Madoff of victims, only eight elected to speak at Bernie’s June 29th sentencing. I sat just behind Weinstein, as she prepared for her big scripted moment — by virtue of alphabetic order, she was the last witness to testify.

She begged the judge to separate Madoff from society so he could never have the “privilege of walking and being among us mortal human beings.”

But what Sheryl Weinstein did not disclose that day to Judge Denny Chin was far more important and she was saving it for her book. In what may win the understatement-of-the-year contest, Weinstein told U.S. District Judge Denny Chin: “I felt it was important for somebody who was personally acquainted with Madoff to speak. My husband and I are not anonymous people to him.”

That day in court, she didn’t lie. But she also failed to tell the truth about her relationship as a “victim” of Bernie. She did not reveal just when it was that she told Ronald, her husband of 37 years, about the affair. (He declined on Thursday to comment to The Daily Beast, saying only that he would try to get word to her that I had called.)

She made no mention of how her sexual relationship with Bernie might have helped her son get a job at Madoff’s firm. She mentioned nothing about Hadassah investments with Madoff, even though she had served at the woman’s organization for 13 years as the chief financial officer.

At court, I sat just behind her with a view of her curly blond hair. I tried to talk to her, but her husband snapped at me to stop bothering his wife. Later, outside the court, I asked: “Can you tell me how well you knew Bernie?” and she said: “I knew him through business, that’s all.” She said she could not even remember the last time – outside of court – she had seen Bernie.

She was happy with the 150-year sentence, saying: “I was very pleased the judge imposed the maximum amount.”

On Thursday, Madoff’s attorney, Ira Sorkin, told The Daily Beast, “She is entitled to say she had an affair and cheated on her husband. She has a right to do that.” Sorkin declined to comment about whether Madoff has confirmed what Sorkin called “the allegation.”

Hadassah spokesman Steve Rabinowitz declined to put a number of Hadassah’s losses with Madoff and would not elaborate about whether any Hadassah official knew their chief financial advisor was having an affair with one of their investment advisors. Rabinowitz said: “We were shocked to hear the news reports of Mrs. Weinstein’s personal admission regarding her relationship with Mr. Madoff. We have no further comment.”

Some of Weinstein’s final words to me were: “I am not ashamed.” That she wouldn’t be, given the humiliation she brought upon her husband, the lies she told to my face and the half-truths she told the court, might have made her perfect for Bernie. Maybe they even had lunch too.

Allan Dodds Frank is a business investigative correspondent who specializes in white collar crime. He also is President of the Overseas Press Club of America, one of the many journalism organizations that protests the arrests of journalists abroad and repression of freedom of speech.