Fingleton enlisted in the military during World War II and was eventually sent to work on media matters for Prime Minister John Curtin and one of his predecessors, Billy Hughes. After the war, Fingleton worked as a political correspondent in Canberra and commentated on cricket during the summer months in Australia and England. He was a prolific author, regarded as one of the finest and most stylish cricket writers of his time, producing many books. Fingleton was known for his forthright opinions and willingness to criticise, especially regarding his colleague Don Bradman, and his cricket reports were published by newspapers in several countries.