Montgomery is the founder of the narrative journalism website Gangrey.com and a 2010 finalist for the Pulitzer Prize in local reporting. He won the Dart Award and Casey Medal for the series For Their Own Good, about abuse at Florida's oldest reform school. His book, Grandma Gatewood's Walk, was a New York Times Bestseller and won a National Outdoor Book Award. He has written three other books: The Leper Spy (2016), The Man Who Walked Backward (2018), and A Shot in the Moonlight (JAN 2021). He lives in Tampa.