He began writing professionally at the age of twenty-two when he sent an unsolicited parody of Time magazine to William F. Buckley Jr., editor of the conservative National Review. Buckley published the piece, and Wills began regularly writing for the magazine, though he was never on the staff full-time. In 1957, on assignment for National Review, he covered the hearings into union corruption conducted by the Senate committee chaired by Senator John McClellan of Arkansas. On the flight back to Chicago from Washington, D.C., Wills met a flight attendant, Natalie Cavallo. The two were married in 1959 and have three children: John Christopher, born in 1960, a research director; Garry Laurence Jr., born in 1961, a law student; and Lydia Mayno, born in 1964, a literary agent.
Inspired by the methodology of one of his first subjects of study, G. K. Chesterton, Wills seeks a "virgin vision" that would renew American values through a return to their construction and implementation. Discarding simplistic narratives of history and historical progress, he challenges the assumptions of coherence that govern the reader's understanding of political institutions; only an active engagement with the complexity of history, a foray "into antiquity's liberating air," can demonstrate the dynamic potential of the ethical and political systems that Americans have inherited.
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