The purpose of this short work is to contextualize the ongoing conflict in Syria through the combined lens of Sun Tzu and Machiavelli, juxtaposed to the normative trend the West has followed ever so ineffectually since the conflict began in Syria. This work is an alternative view of the conflict that should be read as a cautionary tale concerning our lack of proficiency in strategy. It is broken down into three distinct parts. The first part contextualizes the conflict and the actors involved, to include the proxies. The second part lays out the strategic principles of Sun Tzu as pertaining to the conflict to provide a strategic framework with which the reader may make sense of the conflict's complex nature.  The final part focuses on U.S. action keeping in mind Machiavelli within the Syrian conflict as informed by Sun Tzu's strategic principles. Dr. Rubright is a senior faculty member at the Joint Special Operations University and teaches in the fields of special operations, strategy, and counterinsurgency.