The Many Lives of Caroline Kennedy

A world traveler and longtime friend publishes her autobiography, revealing just how much I never knew

Robert Isenberg
Sybarite
7 min readSep 9, 2023

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Of course I met Caroline Kennedy at a community theatre in Costa Rica. You don’t meet people like Caroline waiting in line at the DMV. You don’t make small-talk at a PTA meeting. Caroline must be encountered in some far-flung destination, somewhere glamorous or bizarre, so random and unexpected that bystanders perk up their ears and say, “Wait, you met her where?

(Note: This is not the other Caroline Kennedy. As far as I know, she has no direct relation to the U.S. political dynasty).

Yes, in a theatre, backstage. I was acting in a production of The Glass Menagerie. Caroline was working crew, dressed in an all-black outfit. I’d met everyone on the production except for her. Unsure how to break the ice, I threw out my stock question: “What do you do?”

“I’m a writer,” she said, in a mellifluous English accent designed to say things like, I’m a writer.

We were both living in Costa Rica. I was in my mid-thirties; Caroline was likely my parents’ age, fit and energetic. I lived in a generic, pre-furnished apartment; she lived on a leafy rural estate with its own waterfall. I met a lot of people like Caroline in those days, off-beat expats from Europe, who loved stage productions and had gotten involved in the English-language company, The Little Theatre Group. Many of them, I supposed, fancied themselves writers, so I wasn’t sure what to make of this statement.

“What do you write?” I probed.

Then the reveal: Caroline had co-authored an earth-shattering history of the Profumo Affair, a political-sex scandal that rocked the United Kingdom in the 1960s. The book, How the English Establishment Framed Stephen Ward, was a bare-knuckled account of that era, and the tragic fall-guy at the center of it all, osteopath Stephen Ward. Caroline and her writing partner, Philip Knightly, had tracked down tight-lipped insiders from that era and pried open the story. The book had shocked (and enlightened) readers in the 1980s and even triggered a lawsuit.

“Wow,” I said, vowing to read it as soon as possible. “That’s amazing.”

“The book went out of print some time ago,” Caroline said. “But Andrew Lloyd Webber just adapted it into a musical.”

I gawped. “Andrew Lloyd Webber. Like — the Andrew Lloyd Webber?”

“Oh, yes,” said Caroline in a pleased tone, as if we happened to have the same mutual friend. From there, she referred to Webber as “Andy,” saying he’d relied heavily on her book and corresponded with her personally.

It struck me: This was not some random English expat who liked to occasionally dabble in words. Caroline was the real deal. She had been places, done things. This book had wowed the British press while I was still playing with Legos. I wanted to know everything about her.

This was the tip of the iceberg, it turned out. A friendly relationship with Broadway’s most formidable composer was just a tiny fragment of Caroline’s extraordinary life. For the decade I’ve known her, I’ve heard bits and pieces of her epic story, wondering how so many brow-raising events could fit into a single lifespan. Somehow, the chronology never came into focus; first she’s taking a train across the Soviet Union; then she’s marrying an acclaimed Filipino artist in Manila; then she (if I recall correctly) is hosting radio shows in a Philadelphia sound booth; then she’s hanging out in Manhattan with Norman Mailer. I couldn’t put these happenings in any sensible order.

And then, just recently, it happened. She published another book.

I’ll Be There: Vignettes of an Inveterate Traveler.

Caroline had finished her autobiography, and it was now available to read, from start to finish. The disparate events referenced in our casual conversations had been put into proper order. She’d hinted at this book for years, the way so many people do. And now, it was real.

Not a memoir. Not a “true-life novel.” In her words — an autobiography.

I haven’t seen Caroline in person since 2015, when I left Costa Rica to return to the United States and adopt my son. Our friendship is a peculiar one; affectionate, though we never see each other and sporadically correspond. Mutually admiring, despite the incredible dIfferences in our life paths. Well informed, mostly from social media. Since our time in Costa Rica, I’ve known (from Facebook) when she moved to Newfoundland; I saw pictures of her walks along the rocky coasts. I learned when she later moved to Los Angeles. She speaks often of her nephew, Cary Elwes, who invigorated my childhood by starring in The Princess Bride. I heard, in almost real-time, about the tragic passing of Caroline’s son, Elisar.

This, in the absence of physical proximity, is what has passed for friendship, and I am grateful for that, at least. I’ve missed our occasional coffee date, our backstage chatter, mostly about travel and writing.

Most precious to me was Caroline’s review of my own book, in The Tico Times, when The Green Season was released in 2015. I will always welcome heaps of praise, but it meant so much more coming from a globe-trotting adventurer who had done everything and met everyone.

Still, I have not known Caroline for decades and decades, as so many of her friends have. I witnessed almost none of these phases of her earlier life, like when she lived in New York during the Swinging Sixties, or volunteered at a Croatian refugee camp during the Yugoslav War, or when she talked politics with dissident Filipino artists — at considerable personal risk under the Marcos dictatorship. I never saw her enter a Costa Rican penitentiary as a “prison visitor,” keeping two English inmates company during their darkest times. I wasn’t there, or even born, when she tried to make chit-chat with Lyndon B. Johnson.

It took me some weeks to read I’ll Be There, partly because I’m a slow reader, and partly because my days have been short on free time. But the book is also a typhoon of names and places: a childhood home in the English countryside next to Boris Karloff’s house. A profile about her in the International Herald Tribune, whose headline simply read: “MEET CAROLINE KENNEDY.” Drunken harassment from Frank Sinatra. A starring role in an action movie called El Tigre (after which she learned that press photos of her were hung as pinups). And — why not? — a brush with the Pope. Such stories are not read casually.

In her final chapter she writes: “I’ve played chess with Marlon Brando, played tennis with Al Pacino, sang on stage with Tony Bennett and giggled into my napkin as Monica Lewinsky dipped a cigar in brandy and rolled it seductively against her thigh at dinner…”

From this angle, Caroline looks like the protagonist of a Dos Equis commercial, but I know she’s more than the sum of her celebrity encounters, and her writing attests to that. Caroline is passionate about politics. She has worked as a journalist and covered difficult topics, far more than just Stephen Ward. In I’ll Be There, she writes candidly about her complicated parents, her own divorce, her many friends, and the loss of her son to cancer. She writes about the punishing bureaucratic hurdles to obtain a U.S. green card. In one harrowing account, Caroline smuggles a young refugee from the Balkans to the UK in the back of a truck, where the girl is reunited with her family. Caroline writes in a mannered, factual way, inserting humor here and there. (An insufferable hang-out with actress Rita Gam is particularly funny). Alongside every fact, Caroline reveals her cares and concerns, her impulses and regrets — and above all, her fathomless chutzpah.

When Caroline first told me about this project, she described it as a legacy manuscript, something she could self-publish and share with family and friends. I have stumbled into scores of such books, some authored by members of my own family. I even used to critique these kinds of memoirs for Kirkus Reviews. I know the concept well, and normally I take them in stride. It’s reassuring to know that Aunt So-And-So’s life story is sitting on the shelf, available for any future generation to read, whenever they feel inclined. If for no other reason, a book of memories preserves the history of a beloved family member, and in her own words.

But remember: Caroline is a writer.

So I shouldn’t have been surprised to hear that I’ll Be There is for sale, in paperback and Kindle editions. Indeed, the book is very publicly available; a copy can be delivered to almost any doorstep on Earth. The last Caroline told me, the book had sold more than 300 units; it has skyrocketed to number one in at least one Amazon category; and the acclaimed travel writer Pico Iyer (one of the handful of celebrities I’ve met) had written a glowing review.

In other words, I’ll Be There is not the private album I thought it would be, and the world benefits enormously from this public release. Caroline has given us a thorough portrait of her own life, unsullied by editorial nitpicking. She has proven how much one motivated woman could do, much of it in an era when women were expected to do nothing more than procreate. She has condensed her many incarnations into 326 pages — no small feat — and tells me that friends have torn through the book in a day or two. This praise and profit is a profound reward for all her work. I am, for lack of a fitter phrase, proud of her.

And at this rate, I hope it gets green-lit as an HBO miniseries. Because who knows? Caroline makes just about anything seem possible.

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Robert Isenberg
Sybarite

Robert Isenberg is a freelance writer and multimedia producer based in Rhode Island. Feel free to visit him at robertisenberg.net