In a radio broadcast in 1939 Winston Churchill defined Russia in a famous quip as ‘a riddle wrapped in a mystery inside an enigma.’ The chain of metaphors in Churchill’s famous maxim was to point the difficulty of making sense of the great political transformation Russia had gone through. Though perplexed, Churchill had a key to solve the Russian riddle: the national interest or more precisely ‘historic-life interests.’ The ‘new Middle East’ is also a riddle inside an enigma rolled up in a puzzle mat. The former is difficult to grasp even with metaphors. The national interest is not a ‘key’ either, for it appears more of a political ploy than an analytical edifice that can hardly be applicable to the haplessly artificial regional states. The enigma of the ‘Arab Spring,’ the mystery of the ISIL, the riddle of Russian intervention in Syria and the puzzle of Turkish national interests in the Middle East are few items in the long list of explanandum.