A devout Roman Catholic, Kauffman was also an intimate correspondent of the late Gore Vidal,[1] with whom he shares many ideological similarities.

After earning a Bachelor of Arts degree from the University of Rochester, he went to work as an aide to New York Senator Daniel Patrick Moynihan (which he would later describe as an "anarchist-making experience")[2] in 1981.

Other positions adopted by Kauffman that are considered controversial to both the Left and the Right include his support for the Second Vermont Republic secessionist movement,[5] his admiration for 1972 Democratic presidential nominee George McGovern,[6] his argument that Catholic Worker activist Dorothy Day had much in common with elements of the Right,[7] and his contention that Philip Roth's book The Plot Against America is "the novel that a neoconservative would write, if a neoconservative could write a novel.

"[8] He made the argument in his book Ain't My America that a true conservative would object to an interventionist foreign policy.

: Reflections on the Myth of Progress in America (1998), a collection of (often approving) profiles of the opponents of school consolidation, child labor laws, a standing army, women's suffrage, and the Interstate Highway System, as well as the proponents of homesteading as a means of battling the Great Depression; Dispatches from the Muckdog Gazette: A Mostly Affectionate Account of a Small Town’s Fight to Survive (2003), the story of Batavia and its decline; Look Homeward America: In Search of Reactionary Radicals and Front-Porch Anarchists (2006), a meditation on American political, literary, and artistic figures whose values he admires; and Ain't My America: The Long, Noble History of Anti-War Conservatism and Middle American Anti-Imperialism (2008).