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.
Harvard and World War II .
In a way, JFK's first two years at Harvard echoed his experience at Choate. Again, he felt himself to be in the shadow of his older brother Joe Jr., who was two years ahead of him and pegged as the most intelligent and driven of the Kennedy boys. JFK continued to make only lackluster grades--"gentleman's C's," as the expression went. He wrote occasionally for the Harvard Crimson, the campus newspaper, but had little involvement with campus politics, preferring to concentrate on athletics and his social life. He played football, and was on the JV squad during his sophomore year, but a bad fall led to a rupture of his spinal disc. The injury forced him off the team, and left him with back troubles that would plague him for the rest of his life. Off the field, in Harvard's social scene, he was more successful. He won membership in the Hasty Pudding Society and the Spee Club, one of Harvard's elite "final clubs," where bluebloods mingled and made the connections that kept America's aristocracy running. A contemporary called him "one of the most popular men in our class.