When asked what he did for a living, he would say he was a "newspaper man." Maddrey aspired to work in news reporting early on. As a young boy, he sold the weekly rural newspaper Grit door-to-door, riding his bike on dusty farm roads earning pennies. He worked and interned with the Hertford County Herald, Northampton County News, and The News & Observer. At ECU he was editor-in-chief of the East Carolinian, and at UNC was a reporter for The Daily Tar Heel. Upon graduating from Carolina, Maddrey started the Andrews Journal, a weekly newspaper in Andrews, NC. In 1960 he became the editor and publisher of the Rutherford County News where he worked for eight years.
In 1969 he joined the news staff of the Winston-Salem Journal, retiring in 1995. He served on the copy desk, was assistant state editor, and was the farm editor for 20 years, producing and editing content that told both the human and economic stories of rural life, and writing his weekly Monday column, "Countryside." Maddrey had broad knowledge of the agricultural business of northwest North Carolina. In 1987 he received the National Communication Award from the Soil Conservation Service and many local and state awards for his coverage of agriculture in the region. During his career, he worked in all aspects of the newspaper business, from writing and editing, to typesetting, printing, and selling advertising. What he loved most was meeting people, listening, and writing their stories, especially about those who farmed and the business of farming.