Revolutionary currents with transformative ideals were part of the Sufi religious identity during the late medieval Islamic period. This dissertation tries to make sense of this phenomenon by focusing on the historical evolution of the Bayrami-Malāmi Sufi order within the Ottoman Empire. The scope of the study extends from the beginnings of the order during the ninth/ fifteenth century until its partial demise by the end of the eleventh/seventeenth century. The Bayrami-Malāmiyya was essentially marked by a reaction towards the established Sufi rituals of the time: its adherents refused to wear Sufi clothes, take part in gatherings of remembrance of God, or rely upon imperial endowments for their livelihood. I suggest in this study that Bayrami-Malāmis carried some of the distinguishing signs of religiosity belonging to the anarchic period between the Mongol attacks and the rise of the powerful Islamic Empires. During that time, many local forms of Sufism, which were tied to charismatic and independent communities that were quite prevalent and powerful in their own domains, had emerged. These communities often held a particular vision regarding the saint, whose persona came to be defined in terms exceeding that of a spiritual master, often taking the form of a community elder or a universal savior. Taking their inspiration from this period, Bayrami-Malāmis reconstructed their teachings and affiliations as the social and political conditions shifted in Anatolia. While several pīrs were executed for being heretics and making messianic claims in the sixteenth century, the Order was able to put together a more prudent vision based on the writings of Ibn Arabi (d. 638/1240) during the seventeenth century. After this, it became a secretive order that attracted the upper classes in the imperial city of Istanbul, and extended its influence to imminent poets, bureaucrats, and political figures. This study is essentially concerned with the dynamics of this evolution. It also tries to conceptualize how the teachings of the Order were rooted in the persona of the saint, who was regarded in divine terms and seen as the culmination point of creation. This worldview had the potential to lead to apocalyptic urges that did not harbor the immediate end of the world, but yearned for the beginning of a new era in which people would understand and experience divinity in its true monistic fashion.