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Most people would not describe Christian monks as militaristic. However, there are instances in history when Christians have strayed from their basic pacifist beliefs in the name of defending their religion. The most famous example of this would be the Military Orders of the medieval Crusades, when full scale war was encouraged by the Catholic Church in order to protect the Holy Land. These militant monks formed a new breed of religious organization where brothers were soldiers willing die defending Christianity against the infidel. Although the Order of the Temple, or the Templars, was the most infamous of the Orders, the Order of St. John, or the Hospitallers, was also highly influential. Both came to wield immense power in the twelfth century, despite their counterintuitive identity as religious warriors. Yet it is precisely their contradictory nature that makes them so intriguing. Although they were devout members of a pacifist religion, they were also its dominant military force. By the most basic tenants of Christianity, the Military Orders should never have existed. It is the goal of this paper to uncover the various factors that allowed for their ascendancy through the analysis of primary sources and secondary research. The rise to power of the Military Orders was due to shifts in religious military thought, acquisition of immense wealth through donations from prestigious patrons, ecclesiastical privileges, and a military need in the Crusader states.