This study compares the cold war period and contemporary issues which involve the triangle with a focus on Iraq, Syria and Egypt. It traces turning points in the 20th century, present dilemmas and conclusions in a state of flux. Major conclusions are: that a cold war is re-emerging because of Russia's assertion of its world power status and Washington's claims to world leadership. The other is the conspicuous similarity in Turkey between the Democratic Party (1950-60) and the incumbent government who assume(d) that history, civilizational geopolitics and economy would facilitate transition of its proximate neighbourhood into American new world order(s). Evidence suggests why these efforts failed.