In an email sent the day Epstein returned home, Siegal joked about his first night of freedom — asking how it felt to sleep on Egyptian cotton sheets again, how long his first shower lasted, and whether breakfast included caviar or eggs Benedict. At the time, Siegal was in St. Tropez, celebrating his release from afar.
Over the next decade, Siegal would play a central role in helping Jeffrey Epstein re-enter elite social circles. Her job, as she saw it, was to rehabilitate his image and quietly ease him back into rooms filled with celebrities, politicians, and cultural power brokers.
Siegal made her living throwing high-profile events for movie studios chasing Oscar buzz. She was valued for her connections — a Rolodex that could fill a room with stars, journalists, artists, and decision-makers. Epstein, who helped fund her trips to Cannes and other festivals, became one of her most important clients.
She advised him to move slowly and stay quiet. “Your friends are there for you,” she wrote. “At least the house is drop dead gorgeous.”
That house — Epstein’s seven-story mansion on Manhattan’s Upper East Side — became part of the strategy. Siegal suggested hosting intimate dinners, not too small for such a grand space, featuring “top political and military minds.” Salons like these were her specialty.
In December 2010, Siegal helped organize a dinner at Epstein’s home that included figures such as Charlie Rose, Woody Allen and Soon-Yi Previn, **George Stephanopoulos Katie Couric, and Prince Andrew. In later years, she continued inviting Epstein to screenings, awards events, and private gatherings whenever he was in New York.
Their email correspondence, later released by the Justice Department, shows a relationship that was warm at times, sharply transactional at others. Siegal tried — unsuccessfully — to arrange meetings between Epstein and actresses like Anne Hathaway, as well as discussions involving Bill Gates. At one point, they even exchanged messages about whether a “biggest, most luxurious” private jet might entice stars such as Hugh Jackman or Jessica Chastain to fly with him to the Oscars. None of it happened.
Siegal also acted as an informal media adviser. She warned Epstein when journalists were discussing him behind the scenes and helped him craft responses to negative coverage from outlets like The Daily Beast and Newsweek, both overseen at the time by Tina Brown. In one email, Siegal asked how Epstein could “neutralize” Brown, complaining about her anger toward him.
When writers approached Siegal for comment, Epstein coached her on what to say. In one profile, she was quoted describing him as “brilliant” — almost word for word from his suggestion. She later told a writer for The New York Times that Epstein had “paid a large price” for his crimes and deserved forgiveness, arguing that modern society should not rely on shunning and shame.
Privately, however, her emails were often cutting. She mocked journalists to Epstein while presenting herself publicly as calm and principled.
Siegal also benefitted financially from their relationship. Over the years, Epstein gave her expensive gifts, covered luxury travel, and paid large invoices for her services. In 2011 alone, she billed him $50,000 for five months of work. He also gave her $30,000 as a birthday gift in 2018.
Their familiarity went far beyond business. Epstein once asked Siegal to help him find a woman to have his child, specifying that he wanted someone smart, attractive, and genetically gifted. Siegal joked about her age and said she would search for a “European intellectual,” adding firmly that a “wannabe socialite” would not do.
By 2017, the world Siegal operated in began to collapse. The #MeToo movement toppled powerful men, including Harvey Weinstein and Matt Lauer, both longtime fixtures of elite social life. Epstein, she wrote, suddenly seemed to be “looking better and better” by comparison.
Less than two years later, Epstein would die in jail while awaiting trial on new sex trafficking charges. Siegal’s business collapsed under the weight of her association with him.
Today, Siegal maintains that she never knew about Epstein’s abuse of underage girls and says the public backlash against her has been unfair. “Time to focus on the bad guys,” she has said.
But the emails tell a clear story: for years after his conviction, Epstein was not shunned. With the help of a skilled fixer and a willing social world, he was welcomed back in.
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