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“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.”

— Jacqueline Kennedy

hen John F. Kennedy was born on May 29, 1917, in Brookline, Massachusetts, there were few exaltations or proclamations that he would one day be president, that had already occurred at the arrival of his brother, Joseph P. Kennedy, Jr., two years prior. Following in the shadow of his strong and virile older brother would haunt “Jack” for the first twenty-five years of his life. His father, Joseph P. Kennedy, a banker and businessman turned politician, had high expectations for his brood of nine children, telling them there was no room for losers at the family table.

Rose, the matriarch, was the daughter of Boston’s former mayor, and Jack’s namesake, John “Honey” Fitzgerald, and a devout Catholic who attended Mass daily. Both Joe, Sr. and Rose were the product of families who had emigrated from Ireland after the Great Potato Famine. In the United States, the Fitzgeralds and Kennedys were subject to the ethnic and religious prejudices spreading amongst White Anglo-Saxon Protestant (WASP) communities. This prejudice would prevent Joe Kennedy from pursuing the presidency in 1940 and would later impact the careers of his sons.

At the age of two, Jack developed a severe case of scarlet fever, the first of numerous near-fatal illnesses he would battle in his life. Rose was somewhat aloof to her second son’s medical situations, but his father sat steadfastly by his bed. For a man who rarely showed fear and had never experienced true loss in his life, Joe confessed to his son’s doctor that the toddler’s illness and near-death had shaken him to his core. Over the next few years of his young life, Jack was plagued by mumps, measles, whooping cough, and bronchitis.

A Privileged Upbringing

Growing up, the Kennedy children had the world at their feet. They attended the best schools, had homes in New York, Massachusetts, and Florida, and traveled to Europe frequently, especially upon their father being named Ambassador to Great Britain in 1938. The four boys, Joe, Jr., Jack, Bobby, and Ted, were pushed to follow in the footsteps of their self-made millionaire father, as well as their maternal grandfather, Honey Fitzgerald, and enter the political arena.

Because young Jack was told by his father that he was special, and due to his constant illnesses, he expected everything to be taken care of for him. Maids were at his beck and call, bringing his meals and even laying out his clothes. He was rarely admonished for being consistently late, and he was known to tell shopkeepers that there was no bill too big for his father to pay. Oblivious to the Great Depression and the effect it had on blue-collar workers, teenage Jack was mystified to see people lining the streets waiting for their next meal.

Sent to a boarding school in Connecticut called Choate, where his brother Joe had been a prize pupil and star athlete, Jack spent most of his time in the infirmary with one digestive ailment after another. There was little time for him to focus on his studies. A fervent reader through his illnesses, Jack became an encyclopedia when it came to historical heroes and dates. Joe worried that his sickly son would not develop the persona to achieve the grand plans he dreamed of for his sons, so he went to great lengths to make sure Jack did not develop an inferiority complex and scolded him for his less than average grades.

Due to his constant illnesses, Jack developed a thick skin and became a pro at putting on a brave face even when the prognosis was not promising. After undergoing a series of tests at the Mayo Clinic, he joked in a letter to a friend that the doctors were measuring him for a coffin. With his father’s words that second was never good enough circulating in his mind, Jack decided to make the most of, what he felt, was the little time he had left. Joe, Jr. might have been destined for the presidency, but Jack too was determined to make a name for himself.

The “Most Likely to Succeed”

Determined to do it his way, Jack did not live his life attempting to please his father. On the contrary, it seemed he did everything he could to annoy his father. An unserious student, what little energy Jack had was spent on hijinks and girls. Though handsome, he viewed himself as thin and sickly, and he realized his charisma and personality were his two best assets. After finally realizing he needed to take his studies more seriously, Jack graduated from Choate 64th out of 112 students and was voted “Most Likely to Succeed.”

In 1935, Jack decided to rebel against his father once again and enrolled at Princeton instead of Harvard. Joe chalked it up to his second son feeling inferior to his older brother and deciding to run from the competition; Jack acquiesced and enrolled at Harvard for the fall 1936 semester. When the Kennedy family moved to London in the spring of 1938, Jack remained at Harvard; Joe, Jr. went along as his father’s secretary. After joining the family that summer, Jack too was given a job in his father’s office at the Embassy. This brief stint would open his eyes to the world of international diplomacy and the increasingly dangerous situation simmering in Europe.

A Storm Brewing in Europe

Soon after the Kennedys arrived in London, President Franklin Roosevelt discreetly began planning for the U.S.’s entry into the war. Adolf Hitler, who had conquered Austria, Czechoslovakia, and Poland with the world’s strongest military, needed to be stopped. Joe Kennedy knew the dangers of Hitler, but he viewed going to war as the worst-case scenario. The only option was, as British Prime Minister Neville Chamberlain coined it, “appeasement.”

Ambassador Kennedy publicly applauded Chamberlain when he returned home from Germany in the fall of 1938 after signing the Munich Agreement with Hitler, ceding part of Czechoslovakia to the Nazis with the promise Hitler would halt his aggressions. Privately, Jack questioned if a deal with the devil was possible.

Spending his next semester in London preparing for his senior thesis, Jack met with consulates and other dignitaries and was obsessed with international diplomacy. In March 1939, Jack’s doubts were realized when Hitler seized the rest of Czechoslovakia and continued his conquest. Traveling across the continent and the Middle East, he interviewed people and read every book and newspaper in order to comprehend what was happening. Jack was not surprised when Germany invaded Poland on September 1st and began their ruinous bombings, and soon, Britain found itself engulfed in another World War.

Returning to Harvard and grinding away on his senior thesis titled “Appeasement at Munich,” Jack wrote that Chamberlain’s actions in Munich in 1938 were understandable, yet considerably cowardly and callous. He had not acted in dishonor, as the rest of the free world saw it, but he was considering the size of the British military. Harvard professors were impressed with Jack’s thesis, but no one was more impressed than his father. Joe, Sr. pushed to get the thesis published and had the title changed to Why England Slept. Graduating in June of 1940, the twenty-three-year-old found himself a published author. His father was his number one consumer, buying copies in bulk.

An Emerging Public Servant

Jack attracted attention on his press tour promoting Why England Slept, appearing on radio shows and discussing his opinions on international affairs, and strongly stating that America must be prepared to enter the war. Despite the pride in his son’s literary success, Joe had a different opinion on the war and the direction it was heading in.

The Ambassador was attempting to persuade President Roosevelt to keep America out of the war, stating that England was bound to lose. Roosevelt became increasingly agitated by his Ambassador’s public comments and ordered him home in the fall of 1940. With his unprecedented third-term election around the corner, he could no longer take a chance on Kennedy. Joe Kennedy offered his resignation and was referred to as a “Hitler apologist” by newspapers.

Desperate to boost his faltering ego, Joe decided to give a speech defending his position of appeasement and isolationism. He went to his second son for advice on what to say. Jack gave him plenty of advice on how to word his speech and show he had the best interest of the country in mind, but the two words he told him not to use were “isolationism” and “appeasement”; Joe ignored that advice and became an outsider in Democratic politics. Now the responsibility to rehabilitate the family name was on Joe, Jr. and Jack.

With American intervention in the World War on the brink, the two eldest Kennedy boys did their part by enlisting. Joe, Jr. joined the Navy as a flier and Jack was anxious to join him. Unsurprisingly, his poor health prevented him from doing so. Using steroids to treat his colitis, the drug had done its job in alleviating that problem, but it had also caused deterioration in his backbones. After being rejected, Jack spent five months trying to build up his body to pass the physical; once again he was turned away.

Noting his son’s ambitions, Joe Kennedy arranged for Jack to have a “special” exam; this one he passed. Working at the Naval offices in Washington, Jack spent his days going from party to party, discussing with the elite whether or not the U.S. should enter the war. That question was answered on December 7, 1941, when the air forces of Japan bombed Pearl Harbor, thrusting the country into war. After taking advantage of more family connections, Jack maneuvered his way into a new Patrol Torpedo “PT” boat unit. This was his opportunity to align himself with the countless war heroes he had read about through his illnesses.

The call to action had been sounded, but the young, ambitious Naval officer could not have foreseen just how joining the PT boat unit would lead to such a definitive moment that would shape the character of Jack Kennedy, and the political career of John F. Kennedy.

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