The strategic and operational environment in which the United States military will operate in for the foreseeable future is characterized by its complexity. Historically the United States military has taken a linear approach to understanding the environment as well as problem solving. This linear approach limits the ability of the military to adapt when faced with rivals who do not adhere to similar methodologies. Often when placed in environments whose logic differs from what is expected, the system seems chaotic when in fact it is not. This seeming chaos reduces the effectiveness of military action because the military may try to solve the wrong problem with limited capacity to assess whether their efforts are achieving success. Given that the military will need to be able to operate within this environment, new methodologies have been incorporated into Army staffs including red teams. The author argues that red teaming combats a historical legacy of linear thinking and bounded rationality by providing an alternative perspective to the staff triggering sensemaking. From sensemaking emerges adaptation and creativity better enabling the Army to manage complex systems within limits of tolerance. The author recommends the Army invest additional resources in its red team members in order to enhance their ability to use the considerable arsenal of tools at their disposal.