In 1968, as a student at a New Hampshire boarding school, McConnell canvassed for Minnesota Senator Eugene McCarthy. After working on the 1976 presidential campaign of Jimmy Carter, McConnell earned a Ph.D in history at Columbia University, During this time he became attracted to the neoconservative movement, and began writing for publications such as Commentary and National Review. In 1989, McConnell became an editorial writer and later columnist for the New York Post and served as editorial page editor in 1997. McConnell was fired from the Post later that year.
He has since emerged as one of the leading figures in the broadly defined paleoconservative movement, becoming a prominent supporter of Pat Buchanan. After spending many years as a columnist for the New York Press and Antiwar.com, in 2002 he collaborated with Buchanan and Taki Theodoracopolous in founding The American Conservative, a magazine which has served as a voice for traditionalist conservatives opposed to both liberalism and the policies of George W. Bush.
At the end of 2004, McConnell became the sole editor of TAC; during the year he had written forcefully in favor of John Kerry's candidacy for President, although adding that "If Kerry wins, this magazine will be in opposition from inauguration day forward." He was succeeded as editor by Kara Hopkins and then Daniel McCarthy (in 2010).