After his graduation from law school, Reilly was hired as an attorney working in the antitrust division of the United States Department of Justice.
He joined John F. Kennedy's 1960 presidential campaign and was hired as an aide by Attorney General of the United States Robert F.
[1] Reilly was given the assignment by the Kennedy administration to attend the speech delivered by Martin Luther King Jr. on August 28, 1963, on the steps of the Lincoln Memorial as part of the March on Washington for Jobs and Freedom.
Roger Mudd reported that Reilly told him that he was positioned on the steps of the Lincoln Memorial with a switch that would be used to cut off Dr. King's I Have a Dream speech "if the rhetoric got too inflammatory".
[1] As a member of the Federal Trade Commission in June 1964, Reilly was one of three commissioners who voted in the majority to require that cigarette manufacturers "clearly and prominently" place a warning on packages of cigarettes effective January 1, 1965, stating that smoking is dangerous to health, in line with the warning issued by a special committee formed by the Surgeon General of the United States Luther Leonidas Terry.