Two years later, George W. was sent back East to enroll at Phillips Academy, an elite private prep school in Andover, Massachusetts. At Andover, he was a whirlwind of physical activity, playing varsity baseball and basketball and junior varsity football. In basketball he often made self-deprecating jokes about riding the bench. Instead of trying out for varsity football, he became the squad's head cheerleader. He also organized a stickball league and was nicknamed Tweeds Bush, after the political organizer Boss Tweed. Against the school's intense competition Bush arrayed his sense of humor. "I was able to instill a sense of frivolity," Bush later said. "Andover was kind of a strange experience."
His high school academic record was far from top-notch. However, drawing on his family connections, Bush landed a spot at Yale, where both his father and grandfather had attended. Bush, extremely gregarious and a notoriously poor dresser, made many friends, somehow bridging the growing divide between the public school graduates who were entering Yale and the "preppies." Bush's interest in politics faded temporarily after his father lost a close election for a seat in the U.S.
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