In 1950, Fairlie joined the staff of "The Times", rising at an early age to become the chief writer of its leaders on domestic politics. In 1954, he gave up the security of that post to assume the greater independence of a freelance writer, which he remained until the end of his life. As the author of the "Political Commentary" column in "The Spectator", first under the "nom de plume" "Trimmer", then under his own byline, he helped define the modern political column.