At the age of fifteen, Fingleton took the first steps in his journalism career, when his cousin helped him to become a copy boy with the now defunct Sydney "Daily Guardian". Encouraged by his former headmaster, who had prompted his interest in writing, Fingleton quickly eased into his new career. Fingleton started as a sports reporter, and had a narrow escape when he was sacked by Robert Clyde Packer for breaking a pot, but then reinstated. Fingleton then risked being fired by removing cricket articles written by the famed Neville Cardus from the newspaper's archive against policy for his personal use.