With the birth of his first daughter in 1996, DePastino became a stay-at-home dad, teaching in the evenings at Penn State Beaver and Waynesburg College while finishing his Ph.D. He then revised his dissertation on the history of homelessness into a book, for which he won a National Endowment for the Humanities Fellowship. The result was Citizen Hobo: How a Century of Homelessness Shaped America (2003). After editing, annotating, and introducing the lost classic, The Road by Jack London, DePastino plunged into his Bill Mauldin research. Bill Mauldin: A Life Up Front(2008)received strong reviews, was an Eisner Aweard finalist, and won the Sperber Prize for the best biography of a major media figure. His award-winning double-volume collection of Mauldin's World War II cartoons, Willie & Joe: The WWII Years(2008) was followed in 2011 by Willie & Joe: Back Home, which covers 1945-1946. Commissioned in Battle: A Combat Infantryman in the Pacific, co-authored by Jay Gruenfled, was released by Hellgate Press in early 2012.