Today the United States confronts an uncertain world. The strategic environment has changed. It no longer has one main enemy and a military force to confront that foe. Instead, the United States must be prepared to deal with a multiple of possible threats as its military continues to downsize. This new regional orientation and world situation requires that the US Military be ready to fight simultaneous major regional contingencies to achieve the victories that the American people expect. Therefore, this study examines Field Marshall Wavell's campaigns in the Middle East in WWII to provide a historical case study of a similar situation. There he had to simultaneously conduct a large number of campaigns and operations over four theaters of operations against different enemies under difficult conditions to achieve strategic objectives. It compares this case study with the current strategic military requirements facing the US and current US Military doctrine to determine if the US is prepared to deal with multiple simultaneous regional contingencies. Finally, this monograph indicates that the US Military needs to update both its National Military Strategy and it's doctrine in order to be prepared to fight and win multiple simultaneous major regional contingencies in the future. In addition, this study has indicated a number of implications for the conduct of operational art by the US Military.