As Ms. Simon remembers it, Mr. Starr told the singer he knew her work-her songs include “You’re So Vain,” “Nobody Does It Better” and “That’s the Way I’ve Always Heard It Should Be.” Mr. Starr said that even though her wealth fell below his threshold, he’d take her on as a client and piggyback her account onto Blackstone private-equity deity Pete Peterson’s. She didn’t understand how that would work, but she liked the sound of it. “I thought, ‘Wow. I struck gold.’” He guaranteed a return of 28 percent. “Of course, in retrospect, one sees extremely differently, but I thought he was the type of power that I hadn’t come across.”
Up until recently, Mr. Starr had rarely been photographed without a charming and important person by his side. Around town, he could be seen sipping Diet Coke at the Four Seasons at lunch; or maybe chatting to other guests at Bank of America’s ritzy private client event about his time at the glorious Allen & Co. retreat; or at a charity ball with his nice wide grin, a tie over his modest paunch, his bald head shining in the light and an arm around a good New Yorker like Jimmy Nederlander.
Then there are odder images, like the shots of him with his tattooed and buxom wife, his third, next to bodybuilders at their American Gladiator-themed private cocktail party. But even at the pole-dancing parties she threw, there are happy snapshots of Mr. Starr with David Blaine or Scarface producer Marty Bregman. Al Pacino was a client, too.
So were Mike Nichols, Annie Leibovitz, Neil Simon and Barbara Walters. And during a recording of a conversation with the Los Angeles private investigator Anthony Pellicano that was leaked during his trial, Mr. Starr said the billionaire Mort Zuckerman had been a client and friend, too. “That’s not my recollection,” Mr. Zuckerman, also a Madoff victim, said this week. “I’m going to tell you something: For years I have been asked by various friends in the entertainment world, and I have advised them all to stay away from this guy.”
AT FIRST, THE singer and the adviser got along fine. “Smooth sailing,” Ms. Simon said. “Things looked as though they were moderately improving for the first four or five years.” She didn’t talk to Mr. Starr very often, though she sometimes saw him up on Martha’s Vineyard, where they both knew the humorist Art Buchwald.
When the fall started, it was too slow to bother her. There were sporadic warnings from friends, and there were official complaints in court from clients like Sly Stallone, Wesley Snipes and Joan Stanton, the widow of a Volkswagen mogul and the radio voice of Lois Lane. Ms. Simon got a new assistant, who saw she was being billed for odd storage units-and, somehow, James Taylor’s health insurance. There was a tax mishap. There was a piece of paper sent to Martha’s Vineyard that would have sold off her favorite investment had she signed. There was an enormous line of credit established.
But it was not a crisis. “My life was so filled with so many other problems,” she said. There were health issues to worry about, and her children, plus her relationship with Starbucks, which she eventually sued over an album. “‘We’ve set it up,’ said Ken Starr to me, ‘so that you will not have to worry for the rest of your life.’”
A few months after the collapse of Lehman Brothers, the singer got a call from a woman at the Starr office. She wanted whatever money that was in Ms. Simon’s Martha’s Vineyard account transferred to New York, because there suddenly wasn’t enough money to pay staff members, like the assistant. “That’s when I began to call Ken,” she said.
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