#154: Brookline to Hyannis Port - Growing Up Kennedy; JFK, Part I

Waayyyyy back in Episode 13 (which apparently was nearly four and a half years ago even though it feels much longer than that), I covered the funeral of President John F. Kennedy. At that time I said that I would probably get around to telling the story of how he became eligible for burial at Arlington (I'm talking about his military service, not his election to President of the United States) and that time has finally come. But before we get to his service in the Navy, here is a little bit about his childhood; while it may have seemed idyllic from the outside, it was anything but.

The introduction and transition music heard on the podcast is composed and recorded by the eldest Ghosts of Arlington, Jr. While the rest of his catalogue is quite different from what he's performed for me, you can find his music on bandcamp.com under the names Caladrius and Bloodfeather.

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Transcript

Before we begin today, I want to wish you all a very happy and healthy new year. As we enter 2026, I have been playing around with some format changes for the podcast and I am going to try them out over the next few episodes. They will be minor, but I think they will make the podcast just a little bit better. I know, I know, you’re probably thinking to yourself right now, but Jackson, you already have the best podcast in the world. And while you are right, dear listener - thank you for the kind words by the way - there has to be something I can do to make it even better.

You already know the end of this story arc, I told it WAY back in Episode 13, an episode about the assassination and interment of President John F. Kennedy. At that time, nearly four and a half years ago, I said that I would likely get around to telling the rest of President Kennedy’s story and that day has finally come; so please join me, as over the next 7 or 8 episodes (it's going to be a long one), I tell the story of how a boy born into one of the most privileged families in the history of the United States became a war hero, a lawmaker, and finally, the commander-in-chief.

It is a gray afternoon at a New England prep school in the early 1930s.
Outside, boys run across a muddy field, chasing a football and yelling over the wind. Cleats scrape. A whistle pierces the cold air.

Inside, on an upper floor, one boy is missing from the game.
He is thin, pale, propped up in a narrow bed. A stack of books leans against the wall covering everything from history, to politics, to biographies. He shifts uncomfortably, his back aching, his stomach unsettled in a way he has come to think of as normal.

The nurse has already been by. Another bottle of medicine. Another note home. Another reminder that, in this family, there is one son always on the field, and another just as often on the sidelines.

The boy picks up a book and flips to a well-worn page about a long‑ago war. He reads about leaders making decisions that send young men into danger. He is not yet a leader. He is not yet a war hero. He is just “Jack” Kennedy.

In less than a decade, this same boy will command a small wooden boat in the Pacific, swim for hours through black water with a wounded crewmate in tow, and one day sit in the Oval Office making choices about war and peace for the entire world.

How does a frail, often‑sick kid in a powerful, demanding family become that man?
Let’s find out together.

Welcome back to Ghosts of Arlington. I'm your host, Jackson Irish, tracing the shadows of Arlington National Cemetery through the lives buried there. Today, the humble origins of a sickly- school boy who will go on to wartime heroics and the oval office. Thank you for joining me for Episode 154: Brookline to Hyannis Port: Growing up Kennedy; JFK, Part I.

[THEME MUSIC]

John Fitzgerald Kennedy comes into the world on a late‑spring day - May 29, 1917, to be exact - in Brookline, Massachusetts, just outside of Boston. The Great War has been raging in Europe for years and the United States is on the edge of the new century’s turmoil, but inside the Kennedy house, something else is being built: a family project based on money, faith, and an almost relentless belief in winning.

His father, Joseph P. Kennedy, is already a rising force—sharp in business, restless in politics, determined to turn every advantage into a bigger one. He has grown up outside the old Boston Brahmin elite and has no intention of staying outside for long. To him, his children are not just kids; they’re the future branches of a dynasty he intends to plant firmly in American public life.

His mother, Rose, is equally formidable, but in a different key. She brings structure and piety: daily Mass, strict schedules, high expectations for grades and behavior. In her world, discipline and duty are forms of love. “My mother hugged me, not once.” Jack later recalled. There is a clear message at home—God has given this family much, and much will be required in return.

Jack is the second son. His older brother, Joe Jr., is a bully. Their younger brother Bobby later recalls laying in bed at night as a boy and hearing “the sound of Joe banging Jack’s head against the wall.” Joe, Jr. is also the obvious star: strong, healthy, athletic, and from an early age, talked about as the one who will carry the family name into high office. Jack watches all of this from the next seat at the table—close enough to feel the heat, but not the one everyone assumes will end up in the spotlight.

Around them, siblings keep arriving: a large, noisy, competitive clan. At meals, everyone is expected to argue, to keep up, to have an opinion. Politics, world affairs, business—these are not distant topics; they’re dinner conversation. If you can’t make your case, you’ll be talked over. If you can, you earn a nod from Joe Sr.—small, but powerful approval in a house where praise is rare and success is mandatory.

From the outside, it looks like a golden childhood: big houses, summer trips to the shore, every material comfort. But from the inside, for Jack, it feels like growing up in a pressure cooker where performance and toughness are the default, and weakness is something you hide.

[TRANSITION MUSIC]

There is one problem with being a Kennedy in a family built on strength and endurance: Jack’s body does not cooperate.

From childhood, he is hit with one health problem after another: stomach issues, ear infections, fatigue, a near-fatal case of scarlet fever at age two, chicken pox, appendicitis, mumps, whooping cough, bronchitis, German measles, and probably the most well known of his ailments, chronic back pain. These all create long stretches where he is too weak to keep up. He is in and out of doctors’ offices, hospitals, and infirmaries. Reports and letters home begin to form a pattern: “Jack is ill again. Jack will need to rest. Jack cannot participate.”

In a family where sports are practically a second religion, each absence from the playing field is another mark against him. Joe, Jr. is out breaking records; Jack is back in bed. For a boy already in the shadow of an older brother, the contrast is painful and visible.

But those long hours alone do something that shouldn’t come as a surprise, but does for some - something important. They create space.
While other kids burn off energy outside, Jack reads. He consumes histories, biographies, current events. Stories of kings and knights, generals and diplomats, pirates and adventurers, successes and catastrophic failures. He sees how much can hinge on the judgment of one person at a critical moment.

His widow, Jacquilen - Jackie - said, “History made him what he was. You must think of this little boy, sick so much of the time, reading history, reading the Knights of the Round Table, reading Marlborough. For Jack, history was full of heroes.” 

She continues, “As an adult, he’d read in the strangest ways. He’d read walking, he’d read at the table, at meals, he’d read after dinner; he’d read in the bathtub… he’d really read all times you didn’t think he’d have time to read. He was always reading…”

He also learns something about pain and endurance. Living with constant discomfort becomes normal. Doctors poke and prod him; medications help a little,and then stop helping. He begins to understand that his body is unreliable, but his mind—his curiosity and sharpness—feels like something he can control.

There’s another adaptation that starts to show up: humor. Jack develops a dry, often cutting wit, using jokes to deflect concern, to downplay how bad he feels, to keep attention away from his weaknesses. In a large family, a good line can be as valuable as a strong serve, and it buys him room to maneuver.

When he does return from illnesses, the contrast can be startling. This pale, often absent boy can suddenly shine in conversation, holding his own in arguments about politics or history with people far older than he is. His teachers and relatives see flashes of something more than merely a “sickly second son.”

Those flashes also raise another question: if this is what he can do while constantly knocked down by illness, what might he do if he ever gets fully back on his feet?

Despite Jack’s physical limitations, there is one place he always felt at ease: on the sea. Their father introduced all the Kennedy children to sailing at a young age and Jack took to it effortlessly. By the time he was thirteen, Jack was considered an expert sailor and was often entrusted to take his younger sibling out on the family sailboat. By the time he was fifteen, he was gifted a 25-foot Wianno Senior sloop he named Victura, Latin for “about to conquer.” In college he raced Victura and another boat, Flash II, winning major events like the MacMillian Cup and and the East Coast Collegiate Championships in 1938. Sailing remained a life-long passion and proved to be a vital escape in his later political career. As president, he often escaped the pressure of the White House by sailing up to Massachusetts. 

After his death, his widow Jacquiline said of her husband, he loved the sea “as a child, boy, and man.” Jack himself once wrote, “I have been interested in the sea from my earliest boyhood. My earliest recollections of the United States Navy go back to the day when as a small boy, I used to be taken to the USS Constitution in Charlestown, Massachusetts. The sight of that historic frigate, with its tall spars and black guns, stirred my imagination and made American history come alive for me.”

On a summer day in late August 1930 when he was thirteen, Jack and his sister Kathleen sailed away from Hyannis Port to Osterville, some six miles away. On their way back, the clear skies grew dark and a storm blew in. Waves crashed on the boat threatening to swamp it. Jack leaned into the tiller and kept his sails full as the siblings rushed back home.

While the waves were concerning, the real trouble came from the dense fog that rolled in and blocked all sight of land from view. If Jack made a mistake, if he wandered off course, if he failed to sight land they could be blown out to sea. WIth no radio, no flare gun, no life vests, and only light jackets to keep them warm, they wouldn’t last long. With full confidence in his nautical abilities, Jack pressed on and soon, out of the mist, things came into view.First, a beach, then houses along the shore, and finally, in the distance, a pier, beyond which lay their family’s summer home.

Waiting for the children on the pier were two figures staring out to sea; Jack immediately knew they were - their father, Joe, Sr., and their older brother, Joe, Jr. Jack had made it through the squall, but it would not be the last time he faced danger at sea and saved those close to him.

[TRANSITION MUSIC]

As Jack moves through different schools and eventually into the world of elite prep education, a familiar pattern emerges. On paper, he’s an uneven student: grades that swing from mediocre to excellent, behavior notes that mention charm and trouble in almost the same breath.

In the classroom, when the subject catches his interest—namely history, government, and international affairs—he can be electric. He asks sharp questions, connects distant events, and shows a knack for seeing the personalities behind political decisions. Teachers who take the time to look beyond the absences and last‑minute cramming sometimes sense that beneath the mischievous exterior is a mind tuned toward big, strategic questions.

Outside of class, he gravitates toward the margins of rules. Pranks, late‑night conversations, bending regulations without quite breaking them. In a rigid environment, this raises eyebrows, but it also draws people to him. He is funny, observant, quick with a line that makes everyone in the room feel like they’re sharing a secret.

At the same time, the family world continues to pull him into serious territory. His father’s business ventures and growing political involvement bring stories and visitors from beyond the school gates. Jack hears firsthand accounts of Wall Street speculation, backroom deals, and the inside baseball of Washington, DC and foreign capitals. For a boy already steeped in history books, this real‑time exposure is intoxicating.

He begins to track events overseas. Europe is unstable; authoritarian movements are rising, and the old order that fills his history books seems to be cracking in real time. If you’re a young man who spends a lot of time thinking, but is often unable to do, world politics can feel like the biggest stage imaginable—one where the stakes are life and death, and the players are flawed human beings, not distant legends.

Friends and teachers, looking back, will later say that Jack seemed to come alive when the conversation turned to the wider world. Getting him to focus on routine assignments was a struggle but engaging him on the fate of nations was easy.

In those years, there isn’t yet a clear plan for his own future in politics. That role still seems reserved for his older brother. But seeds are being planted: an understanding of power, an almost instinctive grasp of narrative in public life, and a growing sense that the world is headed toward a crisis that will demand more of his generation than school essays and campus debates.

[TRANSITION MUSIC]

By the time John Kennedy finishes his prep‑school years, several pieces of his character are already in place. He has grown up with every material advantage and every expectation that comes with them. He has lived with a body that seems determined to betray him, forcing him again and again into the role of observer rather than participant.

Out of that tension, something distinctive forms: a quiet resilience, sharpened intellect, and a sense of humor that masks as much as it reveals. He is learning how to endure discomfort, how to watch people closely, how to think strategically about power and responsibility. These are not yet the traits of a president, but they are the raw material.

He is also about to step into a much larger arena. As he moves on to college, the world beyond the Atlantic grows darker. Democracies falter. Dictators push their luck. War clouds gather. And Jack Kennedy, now a young man, will find himself with a front‑row seat to the collapse of peace—and a chance to form his own judgments about why it is happening.

In the next episode, the boy in the infirmary becomes a Harvard student and traveler. We’ll follow Jack into a new phase of education—one that takes him from classrooms to foreign capitals, and sets him on a path toward a war that will test everything he has learned about pain, courage, and leadership.

That’s next time on The Ghosts of Arlington Podcast.

And since it’s been a while since I’ve asked, if you’re enjoying this series, and haven’t yet, please consider following, rating, or sharing the show so others can find it. Also

[Music out.]