in reality, depodesta played football in college and wanted to be a football coach, seen in a photo wearing number 17. after graduating from harvard with a degree in economics, he became an intern for the canadian football league's baltimore stallions in 1995. in early 1996, he got his first baseball job with the cleveland indians, where he worked as a scout. in october 1996, at age 24, he was promoted to the position of advance scout. in october 1998, he became assistant to the general manager for the team. those experiences led to him being hired by beane as his assistant with the oakland a's in november 1998.