What can we learn from an analysis of Iraq’s strategy against Kuwait in 1990-1991 and how can we apply these lessons for possible future operations? Baghdad’s invasion and occupation of Kuwait was a key component of an Iraqi endeavor to achieve regional hegemony and global economic importance. To retain Kuwait, the regime initiated a multifaceted strategy, which encompassed the integration of the diplomatic, informational, military and economic (DIME) instruments of power. This broad strategy was a diminutive time capsule where Iraq exercised nearly every stratagem at its disposal (in an eight-month period) to defeat the Coalition. Although the Iraqi undertaking failed, this epoch is a relevant study for strategists today. There are valuable lessons for the US to draw from a study of the strategies exercised by Iraq during the eight months that encompassed Operations Desert Shield and Storm. This chronicle offers examples on how Islamic regimes attempt to blunt US involvement in the region. The US must be aware of the strategies that Saddam Hussein employed to counter the US led Coalition in 1991, especially since we may revisit that nation. Learning from the experiences of the 1990-1991 confrontation with Saddam Hussein will equip the US with the capacity to anticipate and thwart the various strategies that Baghdad may use in future conflict.