America's national security strategy is a military posture that contains political elements. Mixing strategy and policy with politics is an inherent facet of national security work that requires military leaders to maintain a heightened awareness and skills to operate within the political realm without being caught up in politics. The relationship between military professionals and civilian leaders is built on trust. The respect that it conveys to the military means that it is one of the most venerated vocations in the eyes of the American public. The foundation of the relationship is based upon apolitical advice and counsel on the viability and suitability of military force to achieve national objectives when leaders are contemplating various instruments of national power. The American political arena in contemporary culture is among the most divisive in US history. A case study from our nation's founding through the lens of civil-military relations (CMR) can offer insights for national security professionals. The American people were equally divided between those who supported independence and those who supported the English Crown during the American Revolution. This manuscript provides a case study with perhaps the most infamous treason in American history by analyzing the operating environment in Philadelphia that disenfranchised the revolution's greatest hero, General Benedict Arnold.