Since its 1979 revolution, the Islamic Republic of Iran has garnered a reputation among global powers as the model of a so-called “rogue nation” or a “pariah state.” Orchestrating a range of covert actions in the Middle East, from propping up Shia militia groups in Iraq and funding Hezbollah to allegedly bombing foreign oil assets in the Persian Gulf and clandestinely developing a nuclear capability, the ayatollahs have committed themselves to a campaign frequently labelled as bombastic and illogical, serving only to push Iran further away from international acceptance. This paper argues that such strategic and operational measures are driven neither by political shortsightedness nor revolutionary fanaticism, but rather are a calculated policy that seeks to reassert Iran as a regional powerbroker capable of unilaterally determining events in this volatile crossroads of the world, just like its Persian forebearers of classical antiquity. Through a historical evaluation of the foreign policy objectives of the three major pre-Islamic iterations of Iranian dominance – the Achaemenid, Parthian, and Sassanid empires – this essay concludes that many of the historical precedents of these ancient states mirror that of the modern Islamic Republic, and that the same lessons of their respective formations and demises can be accurately applied to the “Iran Question” today.