In the summer of 1971, reporter Gail Sheehy fled Manhattan every weekend for East Hampton, seeking an escape from what had become a six-month investigation into prostitution in New York City. But instead of tending to her verdant tomato garden, Sheehy found herself drawn down the road to Grey Gardens, a decaying mansion overrun by howling cats and home to Big Edie and Little Edie Beale, dotty and reclusive relatives of former first lady Jacqueline Bouvier Kennedy.
Just a few miles away and 43 summers later, Sheehy sits in a Sag Harbor rental cottage and reflects on “The Secrets of Grey Gardens,” her now-infamous New York magazine cover story about the Beales, outcasts from the wealthy WASP culture that was their birthright. “WASPs are like the Alawites of America, a rare breed,” says the now 70-year-old Sheehy. Looking youthful in jeans and a turquoise linen T-shirt, a helmet of red hair framing her animated face, she is diminutive, quick-witted, and disarmingly warm. (She addresses me in various terms of endearment, as one would an old friend, and invites me to swim in her pool after lunch). It’s a quality that surely worked to her advantage while interviewing the Beales.
“Oh God, that was so much fun,” Sheehy says, wedging a cookie between two heaping scoops of ice cream—dessert. “It was one of my favorite stories, not only because of the characters but because it was a social history, going back to the grandfather who was a paterfamilias and managed everybody’s lives and then cut them all off as heirs. And the Kennedys were in the White House!”
It was one of Sheehy’s breakout pieces of “new journalism,” establishing her as a worthy contemporary of writers like Tom Wolfe, Hunter Thompson, and Joan Didion. As a pioneering female journalist in the ’60s and ’70s, she covered everything from the culture wars—with particular focus on feminism and the sexual revolution—to the emerging civil war in Northern Ireland. Between 1968 and 1977, she would file more than 50 stories for New York magazine. She’s since written 17 books, including the best-selling Passages, which the Library of Congress declared one of the most influential books of our time; blurring the boundaries between self-help and pop psychology, the book was embraced—particularly by American women—as a new way of thinking about adulthood and its accompanying crises. It also established Sheehy as a celebrity author and household name (she milked its success in four subsequent books that were all variations on the Passages theme).
In Daring: My Passages, Sheehy now chronicles the ups and downs of her own life, from the fallout of divorce and single motherhood in her late 20s to her sudden and dizzying success in her 30s, and a life-changing second marriage in her late 40s.
Much of Daring is a tribute to Sheehy’s second husband, the late New York magazine founding editor Clay Felker, and the narrative style of the “new journalism movement” that he tirelessly promoted. (The movement’s stars—like Wolfe and Gay Talese—were among the original members of the New York family, many of whom Felker brought with him from the New York Herald Tribune.) Sheehy recalls fondly the excitement of writing social commentary in the ’60s and ’70s, two decades that “spawned more new lifestyles than could be contained in any magazine.” While radical activists were attempting to change society, New York and its stable of writers were permanently altering the direction of journalism. “Only in retrospect did we appreciate our good fortune in being part of a utopian experiment in American journalism,” she writes. “At the time, we were too busy having fun.”
In Sag Harbor, Sheehy breathlessly recalls the staff feeding off each other’s ideas during weekly editorial lunches. “There was this incredible cross-fertilization at the table. We’d be there for two hours and get so hyped that we would literally run out of the meeting to start doing our research.”
She remembers how the small staff of Felker’s fledgling magazine would gather at The Palm near the United Nations building, which played host to journalists, dignitaries, and future presidents. “George H.W. Bush was our representative to the U.N. [at the time] and would always be at a table in the corner, late, and with a different girlfriend every time,” she says, grinning.
It was an auspicious time to be a reporter, especially as a Columbia Journalism School student studying under cultural anthropologist Margaret Mead. “You had the Black Panthers scaring the shit out of the white radicals, who were desperately trying to compete,” she says of the privileged white students who fancied themselves revolutionaries. “And then you had the early feminists who were making their young husbands shrivel up because they could never do anything right.”
“The earliest [feminists] were the most extreme: the radical redstockings and the Ti-Grace Atkinsons. They were really hard-nosed. And that was before Gloria [Steinem] got into it, too. I was writing about it early on, but I was writing about it in a somewhat satirical way. Because that was sort of the safe way, and it was fun to make fun of it.” But Sheehy wanted to be taken seriously by her feminist colleagues, particularly Steinem, who was fast becoming a leader in the movement. (In 2013, Sheehy wrote about the survival of “the feminist spirit” for The Daily Beast.)
But Daring is more than just a personal memoir; it’s a fast-paced romp through the second half of the 20th century, told through the prism of stories that shaped Sheehy’s career: her first political piece on Bobby Kennedy’s presidential campaign in California; an award-winning series on prostitutes and their pimps; a brush with death in Northern Ireland on Bloody Sunday, which was the impetus for writing Passages; the forgotten Cambodian refugee children who survived Pol Pot’s genocide; profiles of political figures like Margaret Thatcher, George H.W. Bush, and Hillary Clinton.
Her political writings weren’t received without controversy. When Sheehy’s biography of the former First Lady came out in 1999, the Clintons went into attack mode. “Hillary had [Clinton aide] Sidney Blumenthal call people before my book came out, trashing it,” she says. “They are vicious when it comes to trying to silence anyone who has been critical of them.” But she nevertheless declares herself to be sympathetic to the former secretary of state. “I don’t find her to be particularly likeable, but I am a great admirer and I always like to see her succeed.”
At the heart of Daring is Sheehy’s Pygmalion-like romance with her mentor, editor, and husband, Clay Felker. But she acknowledges that their partnership wasn’t always romantic. “It was a creative intimacy from the very beginning,” she explains. Over time, their potent mentor-mentee relationship evolved into a passionate on-again, off-again love affair. But it was intellectual ferment that Sheehy craved above all else. “When we lived together, the most fun we had was reading the papers in the morning over breakfast, digesting the world and spitting it out and arguing about it.”
Like Sheehy, Felker had also been previously married and they were both leery of commitment. Sheehy was in her mid-30s when she broke off the relationship.
“I thought that was the most daring decision of my life,” she remembers. “Because I loved him and didn’t want to lose him. And it could have gone wrong. But I knew I had to strike out on my own and prove myself without a mentor.”
Sheehy reunited with Felker after she finished Passages, which sat on the New York Times bestseller list for three whole years. The two were married in 1984, 22 years after they first met, and remained so until Felker’s death in 2008.
Today, Sheehy is a poster girl for young female journalists: a dogged reporter who seduced wary subjects by charming her way past their defenses and then winning their confidence—pretty much the same way she disarmed this intimidated protégé.
As she gears up for a publicity tour on her most personal work, Sheehy says she’s more emotionally equipped than ever before to dodge the slings and arrows that come with promoting a book.
“I’ve had the experience of having a book praised but then it doesn’t sell. Or not praised but then it sells. Every combination you can think of, so I guess I’m sort of bulletproof at this point.”
She pauses, laughing at herself.
“Well, not really.”