Certain historical events—often, military or strategic in nature— engender obsessions with counter-factual questions. Questions such as, ‘what if Hitler and the Axis had won’, ‘what if Jinnah had died before August 1947’, and ‘what if the South had won the U.S. Civil War’, continually evoke interest amongst the lay public and historians alike. To this league of what-if questions belongs, ‘what if Dara Shukoh had won and Aurangzeb had lost in 1658’. In conventional understanding, Dara Shukoh and Aurangzeb represent the extremes within which lies the entire range of the Indo-Islamic current of Indian civilization. If Aurangzeb stands for a narrow and exclusive understanding of Islam, Dara Shukoh stands for an Islam that was open-ended and inclusive. If Aurangzeb was a master of military methods, Dara was a spiritually inclined Prince. Yet, as contenders to succeed their father, Aurangzeb and Dara Shukoh were no different than other scions in similar predicaments in the medieval world.