The 2012 Defense Strategic Guidance, U.S. policy in the Middle East emphasizes security through collaboration with the Gulf Cooperation Council (GCC) countries. The United States and Saudi Arabia have had a long-standing relationship focused on regional stability and shared security interests. The closeness and strength of the U.S.-Saudi relationship stems from a long relationship based on common interests in oil, strategic regional stability, and Saudi security. The United States Military Training Mission (USMTM) to Saudi Arabia remains a foundational part of this relationship, focusing on “training, advising, and assisting” Saudi Arabian defense services. This military relationship remains intact today because of common interests and strategic objectives; however, it was not born overnight. Rather, the relationship required sixty tumultuous years to mature into what it is today. This is the story of that relationship’s evolution.