The Mayflower Madam Has Some Advice

Three decades after closing up shop, Sydney Biddle Barrows is ready to talk about business, betrayal, and Bezos.

- Glynnis MacNicol

Sydney Biddle Barrows is sitting in an Italian restaurant on the Upper West Side on a blustery February evening, weighing in on the topic that for the last 24 hours has consumed nearly everyone with access to a television or Twitter account: Bradley Cooper and Lady Gaga’s performance at the Oscars the previous evening. Witnessed by millions, including Irina Shayk, Cooper’s partner and mother of their child, who was sitting in the front row, the intimate performance launched a thousand “Are they or aren’t they” takes. “I wouldn’t have liked it,” Barrows says with a cocked eyebrow. “It’s one thing to see it in a film; it’s another to have all that passion playing out directly in front of you.”

Barrows has some experience when it comes to powerful men and their displays of passion. In the early 1980s she was arrested for running an escort service that catered to Manhattan’s elite. Discretion was the secret to her success; even after her arrest she refused to name names. “My attitude was, discretion was one of the main things that they paid for.”

This decades-old entry on her résumé could hardly be more at odds with the refined blond woman in her late sixties who approaches both meal and conversation with a controlled manner that speaks of a bygone era. “I had to learn to use finger bowls to dine at my grandparents’ house,” she says, dabbing her mouth with a cloth napkin. It was this disconnect between her occupation and her upbringing that the tabloids latched onto in the aftermath of her arrest, promptly dubbing her the Mayflower Madam and launching her into a weeks-long inferno of coverage. George Rush Jr., who along with his wife Joanna Molloy penned a gossip column in the Daily News, says, “It was tabloid catnip.”