The authors argue that Umar Khayyam was a philosopher-sage (ḥakīm) and a spiritual-pragmatist whose Rubā‘iyyāt should be seen as a philosophical commentary on the human condition. The salient features of Umar Khayyam’s pioneering work in various branches of mathematics were also discussed. Khayyam’s mathematical genius not only produced the most accurate calendar to date, but the issues he treated remained pertinent up until the modern period. For Khayyam, there are two discourses, each of which pertains to one dimension of human existence: philosophical and poetic. Philosophically, Khayyam was the last Peripatetic in the Persian speaking world before philosophical thinking eclipsed the Eastern part of the Islamic world for several centuries. Khayyam defended rationalism against the rise of orthodoxy and made an attempt to revive the spirit of rationalism which was so prevalent in the first four centuries in Islam. Poetically, Khayyam represents a voice of protest against what he regards to be a fundamentally unjust world. Many people found in him a voice they needed to hear, and centuries after he had died his works became a venue for those who were experiencing the same trials and tribulations as Khayyam had.