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Mamaroneck’s Gail Sheehy (1936-2020) on Fishing in Orienta, and ‘Daring’

Gail Sheehy at the JCC Mid Westchester


Mamaroneck native Gail Sheehy died Monday at age 83.  This is a post we originally published Dec. 4, 2014, after a visit home.


She had me at “Mamaroneck.”

Iconic writer Gail Sheehy perhaps learned to dare when her surrogate Uncle, who worked at a boat yard on Rushmore Avenue in near Orienta Point in Mamaroneck, lent his rowboat to Gail and a friend in the 1950’s. In return, they had to bring him the flounder, bergalls and eel they caught in the Sound. And then skin the eels.

Sheehy, perhaps best known for her book, Passages,  returned to a venue close to the scene of the crime Wednesday to speak at the JCC of Mid-Westchester‘s Bendheim Performing Arts Center in Scarsdale.

Sheehy’s latest book, Daring: My Passages, her 17th, takes on her own life, filled, she says, with decisions to “dare,” where others may have simply hid under the covers. The opposite of daring, after all, said Sheehy, is fear.

And it’s that fear that often leads us, particularly women, around by the scruff of our necks. For Sheehy, this meant daring to crash through the “flamingo pink” ceiling at the New York Herald Tribune and pitch gritty stories to editor Clay Felker (who would become her second husband.) It meant daring to leave a marriage (her first) when being a single mom was far from the norm. It means a life of “the less traveled road, changing what you can, accepting what you cannot change and being willing to ‘fail forward.'”

“I always felt worse when I pulled back from taking a chance,” Sheehy said. “When I fear, I dare.”

Sheehy attended Central School, and graduated from Mamaroneck High School in 1958. “We hung out at Walter’s,” she says. “I’m still hooked on their mustard.” She had an after-school job at a bullion factory in Mamaroneck. (A quick google search reveals this as the Pure Food Co., which made “Herb-Ox”)

While Sheehy was at the Herald Tribune, Felker was incubating the future New York Magazine, with the “new journalism” of which Sheehy would play a part, “saturation reporting,” where reporters were encouraged to find the “why” of the story. She famously posed as a hooker to write about them, traveled with Bobby Kennedy on a tiny plane that she said other, more senior reporters refused to board, interviewed Hillary Clinton in a Ladies’ Room, and tried to find the reason’s for Gary Hart’s catastrophic political fall.

Even if you don’t agree with the conceit of ‘Daring’ in each case (some of it had to be luck–today women and men would fall all over each other to cover stories like these), the American cultural history can be fascinating.

Check out the Sheehy Daring Project on line for more. Perhaps you, too, “dream dangerously.”




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August 26, 2020 5:16 AM

RIP, great adventurer.

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