Jerry Oppenheimer is a super-sleuth who loves to dish. For twenty years, the self-styled “investigative biographer” has been ferreting out the peccadilloes and foibles of the famous, the infamous, the powerful and the supremely well-to-do. He is a raconteur extraordinaire and an interview with the dogged reporter can rapidly turn into a delicious gabfest. Who else can serve up tasty morsels about Martha Stewart, Anna Wintour, Paris Hilton, and is more than willing to share?
Skewering high-wattage females is his shtick. “I like to write about iconic women,” he explains. “Everybody is interested in them and they really sell books…”
He has veered from this formula only twice: once to delve into the private world of Jerry Seinfeld in Seinfeld: The Making of an American Icon, which was not a success even though the comedian had a highly rated show and a huge audience. The fans were “interested only in the show, not the man,” he says.
His second departure is his current take on master swindler Bernie Madoff, Madoff With the Money, which is serialized in The Daily Beast this week. Employing good old-fashioned shoe leather, Oppenheimer went back to Madoff’s roots in Queens, New York to reveal a huckster even in high school, a life-long liar and cheat. As the mind-boggling Ponzi scheme collapsed in December 2008, Oppenheimer was wrapping up his most recent exposé on the legendary Barbie doll and the nefarious dealings of the world famous Mattel company in Toy Monster. Although he was on the road pushing this work, he dropped everything to take on Madoff and “jumped right in.”
On February 1, he began interviewing more than 100 of the felon’s associates, friends, and family, and within six months produced a 90,000-word manuscript. “It was the biggest white-collar crime ever in history,” he enthuses—and a story he simply couldn’t resist.
Oppenheimer, a Philadelphia native, started his career as copy boy at the Philadelphia Inquirer, and moved on the to the Washington Star as an investigative reporter, sometimes butting heads with Carl Bernstein while covering the ins and outs of Watergate. It was at the National Enquirer in the late 1980s that he cut his teeth on celebrity journalism, writing about heartthrob Rock Hudson, who was deep in the closet and desperately trying to disguise his homosexuality and subsequent battle with AIDS. This story morphed into a book, Idol, Rock Hudson. It sold well. Oppenheimer had found his métier.
His next target: Barbara Walters. “It was the ultimate unauthorized biography,” he states. “I loved doing Barbara. She was a big star. Still is.”
He then set his sights on the Kennedy clan and the dysfunctional family of Bobby’s wife Ethel in The Other Mrs. Kennedy. “There were so many Kennedys. Nobody had focused on Ethel and the bizarreness of her family, the Skakels.”
As he was searching for another “woman on the scene,” he came up with an explosive New York Times bestseller, Martha Stewart: Just Desserts, a diatribe about media maven Martha Stewart. “I got the goods and I was prescient,” he says. “I showed what kind of a sociopath she was, which was proved later on when she was convicted and went to jail.”
Profiling hunk JFK, Jr. was next on his schedule. He had a six-figure contract and a lot of “blockbuster” material about the lifestyle of the late president’s son. But he ultimately got cold feet. JFK, Jr. “was such a nice guy and so iconic,” he decided to back off. Also, he did not want to be vilified, hanged in public. He dropped the story.
He picked up with Bill and Hillary Clinton in the controversial State of the Union. In it, he called Hillary’s father, Hugh Rodham, “cheap, aggressive, abusive” and insists there was an anti-Semitic strain on her side of the family. “There were a lot of true but negative things,” he says. These revelations broke just as Hillary was running for a U.S. Senate seat in New York and the brouhaha it engendered ramped up sales and catapulted it into another super-seller.
His most “enjoyable” book, Front Row, was a dissection of Vogue high priestess Anna Wintour. “I loved that project,” he recalls. “It was a juicy, fascinating story.... Anna is a sharp, creative, sexy woman... [And] will always come out on top.’’
The publicity-mad, high-living Hiltons were next on his hit list. He went back to the roots of the dynasty, beginning with the notorious playboy, hotelier Conrad Hilton, and discovered they were all “tabloid train wrecks. It was a continuum of wild, tabloid lifestyles leading up to, guess who. The last one. Paris.”
So what did all his victims have in common? He pauses. “Their streak of extreme deviousness, which comes out in one way or another.” Martha Stewart was the most “fascinating.” Madoff, the most “despicable.”
In the ongoing scandal he singles out Ruth Madoff for special attention. “I think the most interesting character in the story—there’s still a lot to come out—is his wife, Ruth. A woman who has been with Bernie since they were kids in Queens, she’s worked with him, and been by his side for 50 years, was the mate of the man who committed the worst financial crime in history. There’s a lot of fascination with Ruth.” Also, he adds, “She’s smarter than he is.”
During his research of the imprisoned fraudster, he was most surprised by Madoff’s lack of intelligence. “Bernie was not a smart guy. All the people I interviewed never thought he could pull this off alone.... He was not the mastermind,” Oppenheimer insists.
“I don’t know. Maybe [he was] part of a criminal organization who could have conceived of this worldwide scam—not one guy who was lucky enough to get through Hofstra College. He was a moron… I think he’s taking the fall for some other very, very powerful people who masterminded this whole scheme.”
His next person of interest? “Someone in power and very well known. Maybe more than one person. I always keep a list of six or seven ideas.”
Sandra McElwaine is a Washington-based journalist. She has been a reporter for The Washington Star, The Baltimore Sun, a correspondent for CNN and People and Washington editor of Vogue and Cosmopolitan. She writes for The Washington Post, Time and Forbes.