Sixty years after JFK’s death—still wrestling with my Kennedy conundrum

By Michael Patrick O’Brien–

Somehow by accident, coincidence of birth, or other strange circumstance, I developed an emotional connection with an historical figure I’ve never met. His name is John F. Kennedy, and our connection evokes mixed feelings for me.

We’ve had 46 American presidents. I have been around for the last dozen of them—thirteen if you count Dwight D. Eisenhower, who lived in the White House while I occupied my mother’s womb. 

JFK, who died 60 years ago this November, was the president when I was born in 1961. He also was the first Irish Catholic president, a fact that resonates when you have a last name like O’Brien.

My earliest childhood memory involves JFK. I describe it in my 2021 memoir Monastery Mornings:

“One of my first childhood memories, either directly experienced or implanted, is of the day of JFK’s assassination in November 1963, when I was almost three years old. Mom had been vacuuming the living room when CBS anchorman Walter Cronkite reported the awful news from Dallas on our black-and-white, General Electric television set. Mom immediately dropped the vacuum cleaner on the floor, where it remained untouched, next to the television that stayed on for most of the next five days, as the news of JFK’s death and state funeral played out. Our house was enveloped in a wake-like atmosphere as if a close family member had died. An almost identical scene played out five years later when someone shot and killed JFK’s brother, Senator Robert F. Kennedy, in California in June 1968. I remember watching television coverage of RFK’s long funeral train ride from New York City to Washington, DC, when thousands gathered and stood solemnly by the side of the tracks to pay their respects during that last sad journey.”

Of course, the JFK from that story was an idealized myth, and not just in my family. During the 1960 election, Catholic nuns instructed their schoolchildren to go home and tell their parents to vote for Kennedy over Richard Nixon. Now that’s what I call an endorsement.

JFK was intelligent, articulate, charming, and witty, probably all the things for which he is most remembered today. Some of what he did during his thousand days as president, however, was noteworthy too. 

He started the Peace Corps and the Navy SEALs. He avoided a global nuclear conflict during the Cuban Missile Crisis. And although it took him awhile, he eventually laid the groundwork for the civil rights laws that his successor Lyndon B. Johnson pushed through Congress. 

Yet, JFK made policy mistakes too. For example, he escalated the conflict in Vietnam and gave the green light to the ill-fated Bay of Pigs invasion of Cuba.

His untimely and tragic death in his forties at the hands of an assassin supercharged his myth. In the novel Cancer Ward, Aleksandr Solzhenitsyn wrote, “By dying young, a man stays young forever in people’s memory. If he burns brightly before he dies, his brightness shines for all time.”

Over the years, however, other parts of the JFK story have emerged too. Womanizing, and a lot of it. Possible connections to the mob. Hiding relevant facts about his health, and his related use of so many narcotic medications to ease his constant pain. 

As a result, the shiny icon has faded. He was an imperfect human after all. It’s a common arc for mythical figures. Folklore gives way to fact, truth trumps tale, life displaces legend. 

Now, exactly six decades after JFK died, I am left to assess my coincidental but strong emotional connection with both the fabulous myth and the flawed man. How might I do it?

I only know of two ways to get to know a dead person whom you’ve never met. This past year I walked a little in JFK’s shoes and discovered what his best friend had to say about him.

In June, my wife Vicki and I visited the place JFK loved most in the world—Cape Cod in Massachusetts. It was my first time there.

Near as I can tell, JFK seemed more at home in Hyannis and nearby Hyannis Port on the Atlantic coast than anywhere else. He spent his happiest days there, as a boy, a young man, and as president. 

Regular tourists like us cannot get close to the Kennedy homes or compound, but we did see and enjoy the beautiful beaches and waters that JFK loved so much. 

There is a small and charming JFK museum in Hyannis. It shows his more relaxed and human side that emerged on Cape Cod—driving a golf cart, reading books with his children, and on the water with his beloved sailboats.

We also walked to St. Francis Xavier, the simple Catholic church built in 1904 where JFK and his family worshipped. In the 1930s, JFK and his brothers served as altar boys at the modest white clapboard church. 

Their mother—Rose Fitzgerald Kennedy—brought the family to the church regularly every summer, and she attended Mass there until she died in 1995. The family also sought peace and refuge at the same church in 1944 when JFK’s older brother Joseph Kennedy, Jr. died during World War II. 

JFK returned for Sunday Mass at St. Francis several times when he stayed in Hyannis as president. The Secret Service even installed a special “red phone” in the church sacristy with a direct link to the White House, just in case a national or international crisis developed during services.

Despite other institutional failings, the Catholic Church of the time presented its members with a strong message of both personal responsibility and social concern. 

JFK lived a life of privilege on the shores of Cape Cod, but his many hours at places like St. Francis Xavier taught him about personal devotion. They also helped develop his obvious commitment to service and his unmistakable concern about those without the same privilege. 

Yes, JFK strayed from that light, but he also knew how to find his way back to it. Oftentimes, a guide back was his old friend Paul Fay.

Fay was another Irish Catholic, ironically a Republican, who grew up thousands of miles away on the Pacific coast. I met Fay (and the JFK he knew) on the pages of The Pleasure of His Company, a book Fay wrote soon after Lee Harvey Oswald murdered his friend in November 1963.

Fay and Kennedy first met at a U.S. Navy training center in 1942, when the skinny Kennedy asked to play touch football with Fay and his friends. Fay was not impressed, until he saw Kennedy’s sharp elbows and competitive edge helping the other team. The next day, Fay learned that Kennedy was his Navy PT boat instructor.

The two men really bonded, however, on a makeshift naval base in the South Pacific after their separate PT boats became war time casualties in 1943. When a Japanese warship rammed his PT 109, the injured Kennedy still heroically saved many of his men. 

Fay wrote how the convalescing Kennedy attracted people not just because of his “strong sense of responsibility” but also because of “his love for living, and his genuine enjoyment of a joke.” 

Thereafter, Fay helped with all of Kennedy’s runs for Massachusetts public office—Congress, Senate, and then culminating in the presidential election of 1960. Kennedy counted on Fay’s help often, and called him nicknames like “Red” and “the Great Loveable.”

JFK could be somewhat unkind to Fay, perhaps borne out of what one JFK critic has called “the Daisy Buchanan carelessness of the rich that F. Scott Fitzgerald wrote about in The Great Gatsby.” JFK teased Fay mercilessly, sometimes with an edge of superiority. 

The president often emphasized that their appearances together could not detract from JFK’s positive public image. For example, after Fay and his family almost crashed in a Navy plane, JFK seemed almost as concerned about whether the family’s use of the plane would cause a scandal (it didn’t) as he was about their safety.

I think, like me, that Fay’s greatest strength and greatest weakness was his tendency to always try to see the good in people. There was much good to find in his famous friend.

The famous JFK was loyal to the unknown Fay, someone who couldn’t help the president’s political career with money, power, celebrity, or really with anything at all. Kennedy just liked him, and so he asked Fay to be an usher at his wedding and sat with Fay during many of his presidential inauguration celebration events. 

The two men were golfing and dinner buddies. Fay was JFK’s go-to-guy for sneaking out of the White House to watch a movie or for attending Mass at St. Matthew’s Cathedral in Washington, D.C. They took their kids together to stores to buy toys.

JFK was not always a good man, but he was a pretty good friend.

Sixty years after JFK died, it’s hard not to cling to the wonderful Camelot legend that those around him created. 

Yet, myth conceals flesh and blood, so it’s not really a fair or even a good measure of a man. 

Flesh and blood is real. That makes it interesting, but inevitably messy.

Just like JFK. 

*Mike O’Brien (author website here) is a writer and attorney living in Salt Lake City, Utah. Paraclete Press published his book Monastery Mornings, about growing up with the monks at the old Trappist monastery in Huntsville, Utah, in August 2021. The League of Utah Writers chose it as the best non-fiction book of 2022.