The early dismissal of Defense Intelligence Agency (DIA) Director Lieutenant General (LTG) Michael Flynn in 2014 for allegedly “disruptive” leadership raises a host of concerns for military professionals interested in organizational change. LTG Flynn’s attempt to reorganize DIA to provide better combat force support seemed to flag in the face of cultural resistance. It would appear that LTG Flynn’s forceful, top-down approach to change did not fare well at an established bureaucracy with an entrenched cultural identity due to an insufficient coalition of the willing to reinforce his message. In the end, this crippled his efforts and brought about an early end to his tour, despite his clear vision and tough communication. A more consensus-based style might have brought slower but more sustainable change. Also of note, an examination of resources might have begged the question of whether or not DIA should change at all--a point relevant to military change leaders in the current resource constrained environment.