 While he was directing plays, he worked as Director of Communications for Business Communications for the Arts.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 1971–73.Following his time in City Hall, Stewart was Director of Policy for Howard J. Samuels's run for the Governorship of New York in 1974, and also wrote speeches for other Democratic Party campaigns, including Jimmy Carter's successful run for the Presidency of the United States in 1976.