After the war, he was a reporter for the Washington Star-News (later called the Washington Star), focusing on defense and foreign policy issues. When the Star folded in 1981, O'Leary joined the Reagan Administration as press secretary for National Security Advisor William P. Clark, Jr. Soon after the founding of the Washington Times in 1982, he joined that paper as a White House correspondent, became president of the White House Correspondents Association, and ended his career writing a weekly column focused on nostalgic reminiscences of the past.
