Twenty years after John F. Kennedy Jr.’s untimely death, it’s really hard not to dream of what might have been.

As trite as it might seem to say it, he seemed destined for greatness. He was born into the first family of American politics, a family of incredible wealth and influence.

He lived a life of privilege, attending the best schools and traveling the world. He had a reputation as a kind, compassionate leader and a good friend. He displayed character and integrity.

He was so strikingly handsome that he was named People magazine’s “Sexiest Man Alive” in 1988, the only non-entertainer to garner the honor.

As he made his way through adulthood, it was easy to imagine the boy who once played underneath the Resolute desk taking a seat behind it one day.

Alas, such a scene was not meant to be. Kennedy, his wife Carolyn, and her sister Lauren perished in a plane crash while on the way to a family wedding in Hyannisport, Mass. Their bodies were recovered from the ocean floor on July 21, 1999, by a team of Navy divers.

“We dared to think … that this John Kennedy would live to comb gray hair,” said his uncle, Senator Ted Kennedy, in his eulogy. “But like his father, he had every gift but length of years.”

While we might lament the unrealized moxie that was lost in that tragic accident, it’s important not to overlook the moxie evident in JFK Jr’s interrupted life. Here’s my take:

It takes moxie to be ordinary.

Most of the people I interview are notable because they are extraordinary. They live in a way that takes them beyond what most of us can imagine.

But for Kennedy, simply striving to be ordinary was a challenge that took considerable moxie.

From the time of his birth, Kennedy was in the spotlight. He was born just weeks after his father was elected President of the United States, the first child to be born to a president-elect.

In 1963, JFK, Jr. salutes his Father JFK and the 35th POTUS' casket.

And just three years later, the world looked on in shock and grief as little John said goodbye to his father, raising his tiny hand in salute to his father’s casket as it was carried out of St. Matthew’s Cathedral.

The world never really took its eyes off young Kennedy. His father’s assassination redefined American and world politics, and profoundly redefined Kennedy’s life, too.

After Kennedy’s Uncle Bobby was also felled by an assassin’s bullet, his mother Jacqueline sought refuge for herself and her children overseas. She married Greek shipping tycoon Aristotle Onassis in 1968 and moved her daughter and her son to his private island to live.

Kennedy lived with the shadow of his father’s and uncle’s assassinations hanging over him. Until he was sixteen, he lived with constant protection. He never went to a friend’s house to play, to the beach, to the corner store without a Secret Service detail lurking nearby.

After his protection ended and he embarked on young adulthood, he was shadowed again. But this time, the phalanx wasn’t guarding him, it was hunting him. Kennedy was a popular target of the paparazzi.

JFK, Jr. enjoying boating in the Summer of 1993.

What images did his hunters capture? A young man playing football in the park with his friends. Walking down a New York City street deep in conversation with a buddy. Biking to work. All familiar scenes to anyone who has ever lived and worked as a young person starting out in life.

His friends, coworkers, and bosses remember a man who didn’t seek special favors because of his name or wealth or family. They remember a kind and generous guy was working in the same kind of grubby cubicle like everyone else, ate the same lousy takeout, laughed at the same jokes.

Thanks to his wealth and privilege, Kennedy certainly had the option to lead a high-flying life. He chose a life that looked a lot more like the rest of us. It was probably more challenging and complicated than we might imagine. It would have been easier simply to retreat to a wealthy enclave tucked away on an island or in the Hamptons, but Kennedy didn’t.

When you are born into extraordinary circumstances, it takes moxie just to be ordinary, and Kennedy had it.

It takes moxie to chart your own destiny.

So JFK Jr. should have gone to Harvard, got his law degree, run for office, and been well on his way to a run for the White House by the time his life was so tragically cut short.

But he didn’t.

He eschewed the hallowed halls of Harvard in favor of Brown University, where he majored in American Studies. While at Brown, he explored a strong interested in theatre and demonstrated great promise as an actor.

Even so, it seemed difficult for Kennedy to get away from the family business – public service, journalism, the law — entirely.

He spent several years after college working in public service, working in various business development offices in NYC and also with a non-profit. He enrolled in law school and earned his JD from New York University School of Law. After graduation and passing the bar, he went to work as a prosecutor.

He eventually turned to journalism – an echo of his father’s time as a reporter for Hearst – and went on to launch his own magazine, named

JFK Jr. at the 1995 launch of his George Magazine with Supermodel Cindy Crawford as POTUS George Washington

And there are credible reports that before his death, he was considering a run for governor.

When you carry the name of a president and share a surname with some of the most prominent political leaders of the century, running for office seems almost inevitable. But despite the sense of inevitability, Kennedy didn’t seem to fit the typical Kennedy template. It takes moxie to honor and embrace your family’s legacy while pursuing your own destiny, and Kennedy had it.

The curse of moxie.

Much has been made of the “Kennedy curse.” In addition to the assassination of his father and his uncle, Kennedy also lost his uncle Joe Jr. to a plane crash. His Uncle Ted Kennedy also sustained serious injuries in a plane crash which killed one of the pilots and one of his aides. His Michael died in a skiing accident.

Were the deaths and injuries the result of foolhardy choices? Did driving through Dallas in the back of a convertible place the president at risk? Was greeting staffers and well-wishers in a hotel kitchen too great a risk for Bobby? Is flying or skiing too risky?

Perhaps. But I can’t help but think in all these cases the Kennedys were simply living. They were fulfilling their duty to their country, they were working, they were enjoying life.

Even in the case of JFK Jr., his actions were not as risky as they might seem. Flying was one of the few activities and modes of transportation available to him and his wife that offered privacy and independence. It can be argued that they were safer in the air than they might have been on the ground, pursued by paparazzi. If you have any doubts about that, consider how things turned out for Princess Diana.

The reality is that life is inherently risky. In a family as large and active as the Kennedy clan, there’s bound to be tragedy, and those tragedies will be magnified by their family’s prominence and the weight of public scrutiny.

Where do you imagine JFK Jr.’s moxie might have taken him had he lived?

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