In his last year at the Yale School of Drama, he was admitted as a doctoral candidate in comparative literature, which led to his first position as an instructor of English and theatre at Amherst College.
As a student at Oberlin College, he won its only all-school election, and spent several months traveling in and writing about West Africa in the days before the Peace Corps was founded.
There he wrote his first article for a noted public figure, former US Treasury Secretary C. Douglas Dillon, followed by speeches for Katharine Graham of The Washington Post, William S. Paley of CBS, and Arnold Gingrich, the founder of Esquire Magazine, who introduced him to New York Mayor John Lindsay, which led to his position as Chief Speechwriter and Executive Assistant to the Mayor from 1971 to 1973.
[6][7][8] Stewart collaborated with Hertzberg on virtually all the major speeches of the Carter Presidency from 1978 onwards, including the landmark presidential address, the Oval Office "Crisis of Confidence" talk of July 15, 1979.
[5][7][9] Stewart was directly involved in multiple Presidential projects including the Strategic Arms Limitation Talks (SALT II), energy, fiscal and monetary policy, human rights issues, the response to the Soviet invasion of Afghanistan, the first visit to the White House by a Pope in United States history by Pope John Paul II in 1979, three State of the Union addresses, and the farewell speech of President Carter to the nation.
[10] Following his time in the White House, Stewart continued his work in politics as a director of the New York Urban Coalition, and as an advisor to various business, government, and academic forums including the Committee for a Responsible Federal Budget, the National Bureau of Economic Research, the American Business Conference in Washington DC the International Commission for Central American Recovery and Development, the Council on Competitiveness, and the Defence Science Board.
[16][17][18] An important goal for Stewart in re-building the institute was to persuade insurance companies that their reputation is ultimately determined by their market place activities and policies.
The paper's purpose is to create a working model for community-supported journalism similar to listener-supported radio that can be replicated in municipalities all across the country.
The launch of the paper followed the buyout and redirection of the pre-existing and longstanding local newspaper by Roger Ailes, Chairman of Fox News.