America’s Reluctant Prince by Steven M. Gillon

America’s Reluctant Prince: The Life of John F. Kennedy Jr. By Steven M. Gillon Dutton, 2019

University of Oklahoma history professor Steven Gillon ends America’s Reluctant Prince: The Life of John F. Kennedy Jr. with a simple declaration that many readers would say belongs right at the front of the book and that many biographers would say should have been omitted: “I am honored to have called him my friend. My heart ached the day he died. It still does.” 

This opens up a snake-nest of potential problems, and when it comes to the spotlight Kennedy family members, these are very old problems. Is the author retaining objectivity? Is the book in question, however eloquent or intellectual, essentially a work of highbrow hagiography? Is it more a work of friendship than a work of disinterested scholarship? These are the same old questions that were raised by the shelf of books written by the “court historians” of President John Kennedy; no matter how painfully scrupulous those books were, their truth, accuracy, and integrity were questioned fifty years ago, and those same questions have been asked upon the appearance of every book on JFK, RFK, Jacqueline Kennedy, Edward Kennedy, and, inevitably, JFK’s son John, who died twenty years ago at the age of 38. Steven Gillon would have faced those questions in any case. Openly admitting that his heart still aches for his dead friend seems to invite them. 

In the 38 years of his life and in the twenty years since his death, there’ve been many, many books about John Kennedy Jr., ranging from dishy volumes like Christopher Andersen’s The Day John Died to passion-memoirs like Christina Haag’s Come to the Edge. Kennedy was handsome and charismatic, strong-willed but also curiously biddable - a natural focal-point for tall tales, gossip, and headline-making affairs. As his uncle the senator said at his funeral, the world knew his name before he did; by the time he was a teenager, his every move made the papers. When he was a wealthy twenty-something playboy with Manhattan as his playground, those papers were kept busy every day. It must have made living a sincere life nearly impossible; it certainly makes separating flash from substance in a biography all the more challenging. 

Gillon must have been aware of these challenges before he embarked on his book. How do you paint a sober portrait of somebody when there are torrid affairs with Madonna involved? 

He succeeds to a degree no other biographer has done or is likely to do. He can’t work miracles; JFK Jr. could be vain and flighty, and unlike his father, he grew up without the leavening effects of the Second World War, Joe Kennedy, and constant physical pain. Gillon’s account of his friend’s school years brims with bratty privilege, a cocky punk with unlimited funds and a Secret Service detail, and from such an account alone, we might expect the worst of the life to follow. The remarkable thing about that life, well-caught in Gillon’s book, is its almost internal conversion to something less satisfied and more centered. The credit for this slow, subtle transformation is usually given to his indomitable mother, and although she’s a major character in Gillon’s book, the readiest impression from these pages is one of a young man growing less and less satisfied with leading a life of tabloid fodder. 

He met Carolyn Bessette in 1990 while he was still dating the actress Daryl Hannah, and he and Bessette married in 1996. Gillon does his best with the subject, but the marriage was a deeply unhappy one; Bessette cheated on her husband the whole time with male model and Baywatch star Michael Bergin. Had she not died in the same plane crash that killed her husband, the tabloids would almost certainly have spent a year covering an ugly and very public divorce. 

The real accomplishment of America’s Reluctant Prince is the extent to which it rises above the usual froth of wealth and scandal. Gillon does this in large part by focusing on substance instead of scandal. He writes about Kennedy’s more sober sides; he writes about the young man’s social initiatives like Reaching Up. And as did Matt Berman in his book JFK Jr, George, & Me, he writes about Kennedy’s political magazine George - its birth, its launch, its troubles, its legacy. Michael Berman features in that story, as does Kennedy’s other George partner, American Media CEO David Pecker, and Gillon captures the tension these men felt, wondering if they had a genuine product or a star vehicle. Kennedy and his business partners sent out two batches of the premiere issue of George - one batch with Kennedy’s name on the masthead and one without; “If the test without you is successful, then we have a business,” Berman told him. “Otherwise we have a business about you, and that’s not good for either of us.” 

In all of this, Gillon gives his readers a more serious JFK Jr than any version of the man they’ve encountered before. It’s a seriousness that at best appears in shards and glimpses. Kennedy died before he could establish George as a success. He died before he could embark on other publishing ventures. He died before he could write a book. He died before he could enter politics or any other field. Gillon has a radically incomplete story to tell - hard enough for a biographer, necessarily even harder for a friend. It’s the friend - partial, affectionate, sentimental - who gets the final memorable moment in America’s Reluctant Prince, walking in Manhattan after Kennedy’s death: 

I walked the two blocks up Madison Avenue to the Convent of the Sacred Heart, a girls’ school that Caroline Kennedy had once attended and where the reception was being held. I had shut myself off from the news for the past week and thus had been oblivious to the scale of public mourning. Now I experienced it firsthand as I passed hundreds of people lining the sidewalks, standing in the hot sun, wishing to say good-bye to a man who they had never met. Though the crowds were large, they remained remarkably solemn. The city itself seemed uncharacteristically quiet and still. Because of the police blockades, no vehicles filled the streets. Without the sound of car horns or sirens, just an empty silence hung in the air. All week I had been mourning the loss of my friend, not 

realizing that the entire nation was grieving the loss of its reluctant prince. As I looked around I thought, “Yep, you really were special.” 

The author asserts that special status on the part of his friend, but his book - surely the final word on its subject - tries to build its case through documentation and demonstration rather than assertion. The color and flash of John Kennedy Jr’s life is here in these pages, of course - the flash was there, and publishing is a business, after all - but there’s also the strongest sketch yet assembled of what might have been. 

--Steve Donoghue is a founding editor of Open Letters Monthly. His book criticism has appeared in The Boston Globe, The Wall Street Journal, The Historical Novel Society, and The American Conservative. He writes regularly for The National, The Washington Post, The Vineyard Gazette, and The Christian Science Monitor. His website is