The problem with trying to put Whitman in a box is everything he's done to this point in his career has shown he's not in that box. Hes excelled at everything he's done outside if the NFL.
In Josh's 4 years at UW-Lacrosse, the football program was 13-27. At Wash U they are 10-10, so in 6 years as a D3 AD, he's 23-37. During that same 6 year time period Illinois is 31-44. Unfortunately during his time at UWL, his program was found guilty of three major NCAA rules violations.
http://www.d3sports.com/notables/2012/04/uw-lacrosse-cited-for-infraction