Kevin was born in Missoula, Montana and attended the University of Montana, where he played football for two seasons. A linebacker, he finished with two career tackles. At Montana, he studied print journalism and wrote for the student newspaper, the Montana Kaimin, graduating in 2000. He moved to Maryland to work for the Baltimore Sun, where he covered crime, high school sports, college football, Olympic sports and eventually the Ravens. In 2012, he joined ESPN as a senior writer for ESPN the Magazine and ESPN.com. He joined No Laying Up in 2022 as the Editorial Director. His feature writing has been anthologized in the Best American Sports Writing series twice. He lives in Baltimore with his wife and three daughters, and is endlessly searching for ways to overcome the chipping yips.