John Fitzgerald Kennedy, known as JFK, was born on May 29, 1917, in Brookline, Massachusetts. He was the second child of Joseph Kennedy, Sr. and Rose Kennedy, who would eventually have nine children–JFK's older brother Joe Jr., and his younger siblings Rosemary, Kathleen, Eunice, Patricia, Robert and Edward. This generation of Kennedys would eventually become one of America's most famous political families.

Childhood in the Kennedy household was shaped largely by the influence of JFK's father, Joseph, an ambitious man who would achieve great success both in business and politics. The son of a Boston saloon owner, Joseph Kennedy had graduated from Harvard and married into Boston's Irish Catholic upper class in 1914 when he wed Rose, the daughter of the popular mayor John "Honey Fitz" Fitzgerald. At the time of JFK's birth, the United States had just entered World War I; Joseph Sr. left his job at a Boston bank to help manage a shipyard in nearby Quincy, which was busy churning out war vessels. After the war ended, Joseph Sr. began investing on his own, first buying out a chain of New England movie theaters in the early 1920s. He spent time in Hollywood, buying and selling movie companies, before returning in 1930 to New York, where his acumen as a stock market speculator became legendary. He survived and even profited from the Wall Street Crash of 1929, and by the mid-1930s his fortune was immense. In 1949, he established trust funds for his children, guaranteeing each ten million dollars. In 1957, three years before JFK's run for the presidency, Joe Sr.'s fortune was valued at between $200 and $400 million.

With financial success came political involvement. In the 1930s, Joe Sr. became a major backer of Franklin Delano Roosevelt's New Deal, making large donations to the Democratic Party and even penning a book, in 1936, entitled I'm for Roosevelt. Later, his support for some of Roosevelt's more radical fiscal policies cooled, but he remained an enthusiastic Democrat and a famous, if controversial, national figure, holding posts as various as Director of the Securities and Exchange Commission (SEC) and the Ambassador to Great Britain. Nevertheless, Joe Sr. always felt himself something of an outsider in the elite worlds of Boston, New York, and Washington, where a kind of genteel anti-Catholic and anti-Irish sentiment prevailed. Indeed, distrust of Catholics and immigrants was still a powerful force in the country at large, even by the 1940s. Joe Sr. vowed that his children would conquer such forces.

JFK spent his earliest childhood in Brookline, where he and his brother Joe Jr. attended the prestigious Noble and Greenough Lower School, which was filled with the sons of white, Protestant families who had kept the Kennedys and Fitzgeralds out of Boston's country clubs for years. Joe Sr.'s business kept him away from home for long stretches, but he was a formidable presence in his children's lives nevertheless. He encouraged them to be ambitious, emphasizing political discussions at the dinner table (and insisting that business matters were never to be discussed) and demanding a high level of academic achievement from each of them, particularly his sons. They were to compete against one another, it was understood; but in confrontations with outsiders, they were to close ranks. Family loyalty was paramount.

With Joe Sr.'s business ventures concentrated in New York and Hollywood, living in Boston no longer made sense, and in September 1927 the family moved to a rented mansion in Riverdale, a leafy suburb of New York City. Shortly thereafter, they shifted again, to a house in nearby Bronxville. For three years, JFK went to the Riverdale School; this was followed by a year at the Catholic Canterbury School, in New Milford, Connecticut. In the fall of 1931, he enrolled in Choate, a Connecticut boarding school dominated by the old Yankee aristocracy. An arch-conservative institution, Choate excluded Jews and barely tolerated Roman Catholics. JFK was following in his brother's footsteps–Joe Jr., athletic and popular, was a celebrity of sorts around Choate's campus. JFK's time there was less successful: he felt himself to be in his brother's shadow (Joe was a junior when JFK entered), and his grades were mediocre. Rowdy and disobedient, he and his friends were frequently in trouble with the school authorities. His chief gift was for making friends. "When he flashed his smile," the headmaster recalled, "he could charm a bird off a tree."

In 1935, JFK graduated from Choate, ranking 64th in a class of 112. He was a skinny young man with a narrow face and a sickly constitution. He had been frequently ill while at Choate, and after deciding to attend Princeton rather than follow his father and elder brother to Harvard, he had his freshman year cut short by a bout of jaundice. After taking the spring of 1936 off from school, he changed his mind and went to Harvard after all, enrolling in the fall of 1936.

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